JP2020125268A - Method for producing fluorine-containing compound - Google Patents
Method for producing fluorine-containing compound Download PDFInfo
- Publication number
- JP2020125268A JP2020125268A JP2019019009A JP2019019009A JP2020125268A JP 2020125268 A JP2020125268 A JP 2020125268A JP 2019019009 A JP2019019009 A JP 2019019009A JP 2019019009 A JP2019019009 A JP 2019019009A JP 2020125268 A JP2020125268 A JP 2020125268A
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- JP
- Japan
- Prior art keywords
- methyl
- group
- ethyl
- iodo
- trifluoromethyl
- Prior art date
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 87
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 87
- 239000011737 fluorine Substances 0.000 title claims abstract description 87
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 title claims description 80
- -1 olefin compound Chemical class 0.000 claims abstract description 94
- 150000001336 alkenes Chemical class 0.000 claims abstract description 25
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 15
- 150000002081 enamines Chemical class 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 11
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 62
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 5
- 150000005527 organic iodine compounds Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000007259 addition reaction Methods 0.000 abstract description 2
- 150000002896 organic halogen compounds Chemical class 0.000 abstract 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 77
- 238000006243 chemical reaction Methods 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- UOAVDNYZEXTDOI-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane Chemical compound CCCCCCCCC(I)CC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UOAVDNYZEXTDOI-UHFFFAOYSA-N 0.000 description 30
- 239000007788 liquid Substances 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 22
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 13
- SRKZLLOKXQIOQD-UHFFFAOYSA-N 1-(2-methyl-3-phenylprop-1-enyl)pyrrolidine Chemical compound CC(=CN1CCCC1)CC2=CC=CC=C2 SRKZLLOKXQIOQD-UHFFFAOYSA-N 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000012043 crude product Substances 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 6
- BULLJMKUVKYZDJ-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-6-iodohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I BULLJMKUVKYZDJ-UHFFFAOYSA-N 0.000 description 5
- HXCKCCRKGXHOBK-UHFFFAOYSA-N cycloheptane Chemical compound [CH]1CCCCCC1 HXCKCCRKGXHOBK-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- HLLGFGBLKOIZOM-UHFFFAOYSA-N 2,2-diphenylacetaldehyde Chemical compound C=1C=CC=CC=1C(C=O)C1=CC=CC=C1 HLLGFGBLKOIZOM-UHFFFAOYSA-N 0.000 description 4
- HEPHYCJJLAUKSB-UHFFFAOYSA-N 2-methyl-3-phenylpropanal Chemical compound O=CC(C)CC1=CC=CC=C1 HEPHYCJJLAUKSB-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- ZCZFPSNTTZUWFV-UHFFFAOYSA-N CC(CC(C(F)(F)F)(C(F)(F)F)F)(C(O)=O)I Chemical compound CC(CC(C(F)(F)F)(C(F)(F)F)F)(C(O)=O)I ZCZFPSNTTZUWFV-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PRGQAUYEPZLQHK-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodo-7-methyltridecane Chemical compound CCCCCC(C(C)C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)I PRGQAUYEPZLQHK-UHFFFAOYSA-N 0.000 description 3
- SWRIQPRCOGIJGK-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodo-8-methyldodecane Chemical compound CCCCC(C)(CC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)I SWRIQPRCOGIJGK-UHFFFAOYSA-N 0.000 description 3
- MNBTZWGXQAMLCE-UHFFFAOYSA-N 7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluoro-5-iodododecan-1-ol Chemical compound OCCCCC(I)CC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F MNBTZWGXQAMLCE-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RUFRWPTZMPBWPV-UHFFFAOYSA-N C(C(C(=O)O)I)C(C(F)(F)F)(F)F Chemical compound C(C(C(=O)O)I)C(C(F)(F)F)(F)F RUFRWPTZMPBWPV-UHFFFAOYSA-N 0.000 description 3
- FYBHIXBWPBOOMP-UHFFFAOYSA-N CC(CC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(C(=O)O)I Chemical compound CC(CC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(C(=O)O)I FYBHIXBWPBOOMP-UHFFFAOYSA-N 0.000 description 3
- GVGXYDOSBRCEMM-UHFFFAOYSA-N CCCCCCCCC(CC(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)I Chemical compound CCCCCCCCC(CC(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)I GVGXYDOSBRCEMM-UHFFFAOYSA-N 0.000 description 3
- RWWLQFHGAGIOAN-UHFFFAOYSA-N FC(C(C(C(CC(CCCCCCCC)I)(F)F)(F)F)(F)F)(F)F Chemical compound FC(C(C(C(CC(CCCCCCCC)I)(F)F)(F)F)(F)F)(F)F RWWLQFHGAGIOAN-UHFFFAOYSA-N 0.000 description 3
- GIJUSNGHBWBHRH-UHFFFAOYSA-N FC(C(C(CC(CCCCCCCC)I)(F)F)(F)F)(F)F Chemical compound FC(C(C(CC(CCCCCCCC)I)(F)F)(F)F)(F)F GIJUSNGHBWBHRH-UHFFFAOYSA-N 0.000 description 3
- GWKWWOPNQXDSGO-UHFFFAOYSA-N IC(C(=O)OC)CCCCCCCCC Chemical compound IC(C(=O)OC)CCCCCCCCC GWKWWOPNQXDSGO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002497 iodine compounds Chemical class 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 239000003504 photosensitizing agent Substances 0.000 description 3
- 239000000267 (Z)-hex-3-en-1-ol Substances 0.000 description 2
- ZNWVHZQPHQBOIJ-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(3-iododecan-2-yl)cyclohexane Chemical compound CCCCCCCC(C(C)C1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)F)I ZNWVHZQPHQBOIJ-UHFFFAOYSA-N 0.000 description 2
- JDBKHZHDLZKWNG-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(3-iodododecan-2-yl)cyclohexane Chemical compound CCCCCCCCCC(C(C)C1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)F)I JDBKHZHDLZKWNG-UHFFFAOYSA-N 0.000 description 2
- SHLALROYYGLRKL-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(3-iodoheptan-2-yl)cyclohexane Chemical compound CCCCC(C(C)C1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)F)I SHLALROYYGLRKL-UHFFFAOYSA-N 0.000 description 2
- MRZHGSKEVVNJIU-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(3-iodohexan-2-yl)cyclohexane Chemical compound CCCC(C(C)C1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)F)I MRZHGSKEVVNJIU-UHFFFAOYSA-N 0.000 description 2
- IJHLLZHSVZVROY-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(3-iodononan-2-yl)cyclohexane Chemical compound CCCCCCC(C(C)C1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)F)I IJHLLZHSVZVROY-UHFFFAOYSA-N 0.000 description 2
- FLMHPBGEPCJUEC-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(3-iodooctan-2-yl)cyclohexane Chemical compound CCCCCC(C(C)C1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)F)I FLMHPBGEPCJUEC-UHFFFAOYSA-N 0.000 description 2
- QRPHBDTVCWJIDI-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(3-iodotridecan-2-yl)cyclohexane Chemical compound CCCCCCCCCCC(C(C)C1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)F)I QRPHBDTVCWJIDI-UHFFFAOYSA-N 0.000 description 2
- MFADGYGDZRBRBM-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(3-iodoundecan-2-yl)cyclohexane Chemical compound CCCCCCCCC(C(C)C1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)F)I MFADGYGDZRBRBM-UHFFFAOYSA-N 0.000 description 2
- LOSPPRFYAFTQAX-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5-nonafluoro-5-(2-iodo-2-methyldecyl)cyclopentane Chemical compound CCCCCCCCC(C)(CC1(C(C(C(C1(F)F)(F)F)(F)F)(F)F)F)I LOSPPRFYAFTQAX-UHFFFAOYSA-N 0.000 description 2
- UKNQDAOWLLPICO-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5-nonafluoro-5-(3-iododecan-2-yl)cyclopentane Chemical compound CCCCCCCC(C(C)C1(C(C(C(C1(F)F)(F)F)(F)F)(F)F)F)I UKNQDAOWLLPICO-UHFFFAOYSA-N 0.000 description 2
- RHLIUTDQMIAHRD-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5-nonafluoro-5-(3-iodododecan-2-yl)cyclopentane Chemical compound CCCCCCCCCC(C(C)C1(C(C(C(C1(F)F)(F)F)(F)F)(F)F)F)I RHLIUTDQMIAHRD-UHFFFAOYSA-N 0.000 description 2
- LOHZAAJRKJHSGV-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5-nonafluoro-5-(3-iodoheptan-2-yl)cyclopentane Chemical compound CCCCC(C(C)C1(C(C(C(C1(F)F)(F)F)(F)F)(F)F)F)I LOHZAAJRKJHSGV-UHFFFAOYSA-N 0.000 description 2
- UGHUILZQDSSWOZ-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5-nonafluoro-5-(3-iodohexan-2-yl)cyclopentane Chemical compound CCCC(C(C)C1(C(C(C(C1(F)F)(F)F)(F)F)(F)F)F)I UGHUILZQDSSWOZ-UHFFFAOYSA-N 0.000 description 2
- GVKHHGGJDQWZBW-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5-nonafluoro-5-(3-iodononan-2-yl)cyclopentane Chemical compound CCCCCCC(C(C)C1(C(C(C(C1(F)F)(F)F)(F)F)(F)F)F)I GVKHHGGJDQWZBW-UHFFFAOYSA-N 0.000 description 2
- YRPBZXPFUCMCRT-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5-nonafluoro-5-(3-iodooctan-2-yl)cyclopentane Chemical compound CCCCCC(C(C)C1(C(C(C(C1(F)F)(F)F)(F)F)(F)F)F)I YRPBZXPFUCMCRT-UHFFFAOYSA-N 0.000 description 2
- ZAZCUBCYHPODLG-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5-nonafluoro-5-(3-iodotridecan-2-yl)cyclopentane Chemical compound CCCCCCCCCCC(C(C)C1(C(C(C(C1(F)F)(F)F)(F)F)(F)F)F)I ZAZCUBCYHPODLG-UHFFFAOYSA-N 0.000 description 2
- FZPQGKCBFRERIZ-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5-nonafluoro-5-(3-iodoundecan-2-yl)cyclopentane Chemical compound CCCCCCCCC(C(C)C1(C(C(C(C1(F)F)(F)F)(F)F)(F)F)F)I FZPQGKCBFRERIZ-UHFFFAOYSA-N 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- RLWUJHZKEURQBH-UHFFFAOYSA-N 1-(2-ethyl-2-iododecyl)-1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexane Chemical compound CCCCCCCCC(CC)(CC1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)F)I RLWUJHZKEURQBH-UHFFFAOYSA-N 0.000 description 2
- ZSMNSGGBRDKDAW-UHFFFAOYSA-N 1-(2-ethyl-2-iododecyl)-1,2,2,3,3,4,4,5,5-nonafluorocyclopentane Chemical compound CCCCCCCCC(CC)(CC1(C(C(C(C1(F)F)(F)F)(F)F)(F)F)F)I ZSMNSGGBRDKDAW-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- ZHDDGKNACKSKEF-UHFFFAOYSA-N 2,3-diphenylpropanal Chemical compound C=1C=CC=CC=1C(C=O)CC1=CC=CC=C1 ZHDDGKNACKSKEF-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- IQVAERDLDAZARL-UHFFFAOYSA-N 2-phenylpropanal Chemical compound O=CC(C)C1=CC=CC=C1 IQVAERDLDAZARL-UHFFFAOYSA-N 0.000 description 2
- NPPSLFJBIKCAFD-UHFFFAOYSA-N 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodononanoic acid Chemical compound OC(=O)C(I)CC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F NPPSLFJBIKCAFD-UHFFFAOYSA-N 0.000 description 2
- QABIXMMBWTXMKQ-UHFFFAOYSA-N 7-ethyl-1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iododecane Chemical compound CCC(C(CC)I)C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F QABIXMMBWTXMKQ-UHFFFAOYSA-N 0.000 description 2
- AIKCKPRBMLCNQS-UHFFFAOYSA-N C(C(C(=O)O)I)C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F Chemical compound C(C(C(=O)O)I)C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F AIKCKPRBMLCNQS-UHFFFAOYSA-N 0.000 description 2
- MWEVKPXYWAANQS-UHFFFAOYSA-N C(C(C(=O)O)I)C(C(C(C(F)(F)F)(F)F)(F)F)(F)F Chemical compound C(C(C(=O)O)I)C(C(C(C(F)(F)F)(F)F)(F)F)(F)F MWEVKPXYWAANQS-UHFFFAOYSA-N 0.000 description 2
- WNAJYKXVPSIIQI-UHFFFAOYSA-N C(C(C(=O)O)I)C(C(C(F)(F)F)(F)F)(C(F)(F)F)F Chemical compound C(C(C(=O)O)I)C(C(C(F)(F)F)(F)F)(C(F)(F)F)F WNAJYKXVPSIIQI-UHFFFAOYSA-N 0.000 description 2
- RHDZARKGDBWIMH-UHFFFAOYSA-N C(C(C(=O)O)I)C(C(F)(F)F)(C(F)(F)F)F Chemical compound C(C(C(=O)O)I)C(C(F)(F)F)(C(F)(F)F)F RHDZARKGDBWIMH-UHFFFAOYSA-N 0.000 description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
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- 230000002950 deficient Effects 0.000 description 1
- BZFOTDCOPAWHTP-UHFFFAOYSA-N diethyl 2,2-difluoro-4-iodo-4-methylpentanedioate Chemical compound CCOC(=O)C(C)(CC(C(=O)OCC)(F)F)I BZFOTDCOPAWHTP-UHFFFAOYSA-N 0.000 description 1
- FCAGIIFAVLGOII-UHFFFAOYSA-N diethyl 2,2-difluoro-4-iodopentanedioate Chemical compound CCOC(=O)C(I)CC(F)(F)C(=O)OCC FCAGIIFAVLGOII-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- NHERJAOJDYECLT-UHFFFAOYSA-N dimethyl 2,2-difluoro-4-iodo-4-methylpentanedioate Chemical compound CC(CC(C(=O)OC)(F)F)(C(=O)OC)I NHERJAOJDYECLT-UHFFFAOYSA-N 0.000 description 1
- MYVJFXQZJPEAHF-UHFFFAOYSA-N dimethyl 2,2-difluoro-4-iodopentanedioate Chemical compound COC(=O)C(CC(C(=O)OC)(F)F)I MYVJFXQZJPEAHF-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- OKXPUQMEFURMRX-UHFFFAOYSA-N ethyl 2,2-difluoro-2-(2-iodocycloheptyl)acetate Chemical compound CCOC(=O)C(C1CCCCCC1I)(F)F OKXPUQMEFURMRX-UHFFFAOYSA-N 0.000 description 1
- IRHNYNMTZJJHNF-UHFFFAOYSA-N ethyl 2,2-difluoro-2-(2-iodocyclohexyl)acetate Chemical compound CCOC(=O)C(F)(F)C1CCCCC1I IRHNYNMTZJJHNF-UHFFFAOYSA-N 0.000 description 1
- BWUCFLQKWJWQDS-UHFFFAOYSA-N ethyl 2,2-difluoro-2-(2-iodocyclooctyl)acetate Chemical compound CCOC(=O)C(C1CCCCCCC1I)(F)F BWUCFLQKWJWQDS-UHFFFAOYSA-N 0.000 description 1
- YOFQCYGHZYOPGT-UHFFFAOYSA-N ethyl 2,2-difluoro-2-(2-iodocyclopentyl)acetate Chemical compound CCOC(=O)C(C1CCCC1I)(F)F YOFQCYGHZYOPGT-UHFFFAOYSA-N 0.000 description 1
- HGWXXIZVRRTDKT-UHFFFAOYSA-N ethyl 2,2-difluoro-2-iodoacetate Chemical compound CCOC(=O)C(F)(F)I HGWXXIZVRRTDKT-UHFFFAOYSA-N 0.000 description 1
- DSTQCIMXLFNVJA-UHFFFAOYSA-N ethyl 2,2-difluoro-4-iodo-3-methyldodecanoate Chemical compound CCCCCCCCC(C(C)C(C(=O)OCC)(F)F)I DSTQCIMXLFNVJA-UHFFFAOYSA-N 0.000 description 1
- POZLZMQLIHDWBW-UHFFFAOYSA-N ethyl 2,2-difluoro-4-iodo-3-methyltridecanoate Chemical compound CCCCCCCCCC(C(C)C(C(=O)OCC)(F)F)I POZLZMQLIHDWBW-UHFFFAOYSA-N 0.000 description 1
- DBDBGVWUJLGZEG-UHFFFAOYSA-N ethyl 2,2-difluoro-4-iodo-4,4-diphenylbutanoate Chemical compound CCOC(=O)C(CC(C1=CC=CC=C1)(C2=CC=CC=C2)I)(F)F DBDBGVWUJLGZEG-UHFFFAOYSA-N 0.000 description 1
- BFCXRXVOJDYFSI-UHFFFAOYSA-N ethyl 2,2-difluoro-4-iodo-4-methyldecanoate Chemical compound CCCCCCC(C)(CC(C(=O)OCC)(F)F)I BFCXRXVOJDYFSI-UHFFFAOYSA-N 0.000 description 1
- HVKLUJZCEINIDX-UHFFFAOYSA-N ethyl 2,2-difluoro-4-iodo-4-methyldodecanoate Chemical compound CCCCCCCCC(C)(CC(C(=O)OCC)(F)F)I HVKLUJZCEINIDX-UHFFFAOYSA-N 0.000 description 1
- GUSUSFWZGBTDFO-UHFFFAOYSA-N ethyl 2,2-difluoro-4-iodo-4-methylheptanoate Chemical compound CCCC(C)(CC(C(=O)OCC)(F)F)I GUSUSFWZGBTDFO-UHFFFAOYSA-N 0.000 description 1
- ZTXWJPXAIOLNKF-UHFFFAOYSA-N ethyl 2,2-difluoro-4-iodo-4-methylnonanoate Chemical compound CCCCCC(C)(CC(C(=O)OCC)(F)F)I ZTXWJPXAIOLNKF-UHFFFAOYSA-N 0.000 description 1
- USHQVZNWWUCZOU-UHFFFAOYSA-N ethyl 2,2-difluoro-4-iodo-4-methyloctanoate Chemical compound CCCCC(C)(CC(C(=O)OCC)(F)F)I USHQVZNWWUCZOU-UHFFFAOYSA-N 0.000 description 1
- PBPNJTJFDPCVTF-UHFFFAOYSA-N ethyl 2,2-difluoro-4-iodo-4-methyltetradecanoate Chemical compound CCCCCCCCCCC(C)(CC(C(=O)OCC)(F)F)I PBPNJTJFDPCVTF-UHFFFAOYSA-N 0.000 description 1
- LMTJOQASBDYGJK-UHFFFAOYSA-N ethyl 2,2-difluoro-4-iodo-4-methyltridecanoate Chemical compound CCCCCCCCCC(C)(CC(C(=O)OCC)(F)F)I LMTJOQASBDYGJK-UHFFFAOYSA-N 0.000 description 1
- XJRKCNOLDUBQTL-UHFFFAOYSA-N ethyl 2,2-difluoro-4-iodo-4-methylundecanoate Chemical compound CCCCCCCC(C)(CC(C(=O)OCC)(F)F)I XJRKCNOLDUBQTL-UHFFFAOYSA-N 0.000 description 1
- CVKHIWSGHLWGMF-UHFFFAOYSA-N ethyl 2-iodo-3-(1,2,2,3,3,4,4,5,5-nonafluorocyclopentyl)propanoate Chemical compound CCOC(=O)C(CC1(C(C(C(C1(F)F)(F)F)(F)F)(F)F)F)I CVKHIWSGHLWGMF-UHFFFAOYSA-N 0.000 description 1
- WZQDKMOIDWGJST-UHFFFAOYSA-N ethyl 2-iodohexanoate Chemical compound CCCCC(I)C(=O)OCC WZQDKMOIDWGJST-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- PUPUBXYPDHVZQH-UHFFFAOYSA-N ethyl 3-ethyl-2,2-difluoro-4-iodononanoate Chemical compound CCCCCC(C(CC)C(C(=O)OCC)(F)F)I PUPUBXYPDHVZQH-UHFFFAOYSA-N 0.000 description 1
- CMRHQGSGVQPDPT-UHFFFAOYSA-N ethyl 4,5,5,6,6,7,7,7-octafluoro-2-iodo-2-methyl-3-(trifluoromethyl)heptanoate Chemical compound CCOC(=O)C(C)(C(C(C(C(C(F)(F)F)(F)F)(F)F)F)C(F)(F)F)I CMRHQGSGVQPDPT-UHFFFAOYSA-N 0.000 description 1
- MGLWFGBGRPYZMK-UHFFFAOYSA-N ethyl 4-ethyl-2,2-difluoro-4-iodoheptanoate Chemical compound CCCC(CC)(CC(C(=O)OCC)(F)F)I MGLWFGBGRPYZMK-UHFFFAOYSA-N 0.000 description 1
- KGYWGLOJRTYLHF-UHFFFAOYSA-N ethyl 4-ethyl-2,2-difluoro-4-iodohexanoate Chemical compound CCC(CC)(CC(C(=O)OCC)(F)F)I KGYWGLOJRTYLHF-UHFFFAOYSA-N 0.000 description 1
- ALYPHBDOEKEYAK-UHFFFAOYSA-N ethyl 4-ethyl-2,2-difluoro-4-iodooctanoate Chemical compound CCCCC(CC)(CC(C(=O)OCC)(F)F)I ALYPHBDOEKEYAK-UHFFFAOYSA-N 0.000 description 1
- OSXVEGWCOBTMCS-UHFFFAOYSA-N ethyl 4-ethyl-2,2-difluoro-4-iodotetradecanoate Chemical compound CCCCCCCCCCC(CC)(CC(C(=O)OCC)(F)F)I OSXVEGWCOBTMCS-UHFFFAOYSA-N 0.000 description 1
- AQUZEXYZLQJQPM-UHFFFAOYSA-N ethyl 4-ethyl-2,2-difluoro-4-iodotridecanoate Chemical compound CCCCCCCCCC(CC)(CC(C(=O)OCC)(F)F)I AQUZEXYZLQJQPM-UHFFFAOYSA-N 0.000 description 1
- VCZCBLCPYXTPCC-UHFFFAOYSA-N ethyl 4-ethyl-2,2-difluoro-4-iodoundecanoate Chemical compound CCCCCCCC(CC)(CC(C(=O)OCC)(F)F)I VCZCBLCPYXTPCC-UHFFFAOYSA-N 0.000 description 1
- LLGWTINMSLTDMP-UHFFFAOYSA-N ethyl 4-iodotetradecanoate Chemical compound CCCCCCCCCCC(I)CCC(=O)OCC LLGWTINMSLTDMP-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- WZHKDGJSXCTSCK-UHFFFAOYSA-N hept-3-ene Chemical compound CCCC=CCC WZHKDGJSXCTSCK-UHFFFAOYSA-N 0.000 description 1
- UIZVMOZAXAMASY-UHFFFAOYSA-N hex-5-en-1-ol Chemical compound OCCCCC=C UIZVMOZAXAMASY-UHFFFAOYSA-N 0.000 description 1
- GOQJMMHTSOQIEI-UHFFFAOYSA-N hex-5-yn-1-ol Chemical compound OCCCCC#C GOQJMMHTSOQIEI-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- PDJAZCSYYQODQF-UHFFFAOYSA-N iodine monofluoride Chemical compound IF PDJAZCSYYQODQF-UHFFFAOYSA-N 0.000 description 1
- HLXICRJOFXSTBV-CMDGGOBGSA-N methyl (e)-dec-3-enoate Chemical compound CCCCCC\C=C\CC(=O)OC HLXICRJOFXSTBV-CMDGGOBGSA-N 0.000 description 1
- PJTYJAOQKPHJKS-UHFFFAOYSA-N methyl 2,2-difluoro-2-(2-iodocycloheptyl)acetate Chemical compound COC(=O)C(C1CCCCCC1I)(F)F PJTYJAOQKPHJKS-UHFFFAOYSA-N 0.000 description 1
- WPUPZLQQEIFGFA-UHFFFAOYSA-N methyl 2,2-difluoro-2-(2-iodocyclooctyl)acetate Chemical compound COC(=O)C(C1CCCCCCC1I)(F)F WPUPZLQQEIFGFA-UHFFFAOYSA-N 0.000 description 1
- CWGBOFQMEZSMFN-UHFFFAOYSA-N methyl 2,2-difluoro-2-(2-iodocyclopentyl)acetate Chemical compound COC(=O)C(C1CCCC1I)(F)F CWGBOFQMEZSMFN-UHFFFAOYSA-N 0.000 description 1
- KAHKWAVXEPUDOR-UHFFFAOYSA-N methyl 2,2-difluoro-2-iodoacetate Chemical compound COC(=O)C(F)(F)I KAHKWAVXEPUDOR-UHFFFAOYSA-N 0.000 description 1
- ZSEZQMKLAPROFP-UHFFFAOYSA-N methyl 2,2-difluoro-4-iodo-3-methyldecanoate Chemical compound CCCCCCC(C(C)C(C(=O)OC)(F)F)I ZSEZQMKLAPROFP-UHFFFAOYSA-N 0.000 description 1
- RYLKIAANXDYHIY-UHFFFAOYSA-N methyl 2,2-difluoro-4-iodo-3-methyldodecanoate Chemical compound CCCCCCCCC(C(C)C(C(=O)OC)(F)F)I RYLKIAANXDYHIY-UHFFFAOYSA-N 0.000 description 1
- YPGSCWIBDGFQOS-UHFFFAOYSA-N methyl 2,2-difluoro-4-iodo-3-methylheptanoate Chemical compound CCCC(C(C)C(C(=O)OC)(F)F)I YPGSCWIBDGFQOS-UHFFFAOYSA-N 0.000 description 1
- FJTDGUKOWLOKLW-UHFFFAOYSA-N methyl 2,2-difluoro-4-iodo-3-methylhexanoate Chemical compound CCC(C(C)C(C(=O)OC)(F)F)I FJTDGUKOWLOKLW-UHFFFAOYSA-N 0.000 description 1
- QAINBZWHBZOTMG-UHFFFAOYSA-N methyl 2,2-difluoro-4-iodo-3-methylnonanoate Chemical compound CCCCCC(C(C)C(C(=O)OC)(F)F)I QAINBZWHBZOTMG-UHFFFAOYSA-N 0.000 description 1
- WMGYMKZAQINEDP-UHFFFAOYSA-N methyl 2,2-difluoro-4-iodo-3-methyloctanoate Chemical compound CCCCC(C(C)C(C(=O)OC)(F)F)I WMGYMKZAQINEDP-UHFFFAOYSA-N 0.000 description 1
- TYGQKUXTXPVMHZ-UHFFFAOYSA-N methyl 2,2-difluoro-4-iodo-3-methylpentanoate Chemical compound CC(C(C)I)C(C(=O)OC)(F)F TYGQKUXTXPVMHZ-UHFFFAOYSA-N 0.000 description 1
- FREHTHNDFXUOGP-UHFFFAOYSA-N methyl 2,2-difluoro-4-iodo-3-methyltetradecanoate Chemical compound CCCCCCCCCCC(C(C)C(C(=O)OC)(F)F)I FREHTHNDFXUOGP-UHFFFAOYSA-N 0.000 description 1
- RTFUWIJUMIEUCR-UHFFFAOYSA-N methyl 2,2-difluoro-4-iodo-3-methyltridecanoate Chemical compound CCCCCCCCCC(C(C)C(C(=O)OC)(F)F)I RTFUWIJUMIEUCR-UHFFFAOYSA-N 0.000 description 1
- YDVCXLNAVIMGCE-UHFFFAOYSA-N methyl 2,2-difluoro-4-iodo-4-methylhexanoate Chemical compound CCC(C)(CC(C(=O)OC)(F)F)I YDVCXLNAVIMGCE-UHFFFAOYSA-N 0.000 description 1
- JGMXUWCKZXOFKN-UHFFFAOYSA-N methyl 2,2-difluoro-4-iodo-4-phenylbutanoate Chemical compound COC(=O)C(CC(C1=CC=CC=C1)I)(F)F JGMXUWCKZXOFKN-UHFFFAOYSA-N 0.000 description 1
- ZYUBRBUXFGPQTC-UHFFFAOYSA-N methyl 2,2-difluoro-6-hydroxy-4-iodohex-3-enoate Chemical compound COC(=O)C(C=C(CCO)I)(F)F ZYUBRBUXFGPQTC-UHFFFAOYSA-N 0.000 description 1
- CSSYKHYGURSRAZ-UHFFFAOYSA-N methyl 2,2-difluoroacetate Chemical compound COC(=O)C(F)F CSSYKHYGURSRAZ-UHFFFAOYSA-N 0.000 description 1
- NBINNYQISJAKHQ-UHFFFAOYSA-N methyl 2-iodo-3-(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)propanoate Chemical compound COC(=O)C(CC1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)F)I NBINNYQISJAKHQ-UHFFFAOYSA-N 0.000 description 1
- BMQVVHLZAWQQEZ-UHFFFAOYSA-N methyl 2-iodo-3-(1,2,2,3,3,4,4,5,5-nonafluorocyclopentyl)propanoate Chemical compound COC(=O)C(CC1(C(C(C(C1(F)F)(F)F)(F)F)(F)F)F)I BMQVVHLZAWQQEZ-UHFFFAOYSA-N 0.000 description 1
- VBYFLCZOLALVLX-UHFFFAOYSA-N methyl 2-iodotetradecanoate Chemical compound CCCCCCCCCCCCC(I)C(=O)OC VBYFLCZOLALVLX-UHFFFAOYSA-N 0.000 description 1
- FWFCIERVUSWLAA-UHFFFAOYSA-N methyl 3-ethyl-2,2-difluoro-4-iododecanoate Chemical compound CCCCCCC(C(CC)C(C(=O)OC)(F)F)I FWFCIERVUSWLAA-UHFFFAOYSA-N 0.000 description 1
- RJXYMVOZXRYUOH-UHFFFAOYSA-N methyl 3-ethyl-2,2-difluoro-4-iodododecanoate Chemical compound CCCCCCCCC(C(CC)C(C(=O)OC)(F)F)I RJXYMVOZXRYUOH-UHFFFAOYSA-N 0.000 description 1
- NCEVXMIBKOPPDQ-UHFFFAOYSA-N methyl 3-ethyl-2,2-difluoro-4-iodoheptanoate Chemical compound CCCC(C(CC)C(C(=O)OC)(F)F)I NCEVXMIBKOPPDQ-UHFFFAOYSA-N 0.000 description 1
- HJQKDZGPDURGLA-UHFFFAOYSA-N methyl 3-ethyl-2,2-difluoro-4-iodohexanoate Chemical compound CCC(C(CC)I)C(C(=O)OC)(F)F HJQKDZGPDURGLA-UHFFFAOYSA-N 0.000 description 1
- UOGSCDCHYFXJCQ-UHFFFAOYSA-N methyl 3-ethyl-2,2-difluoro-4-iodononanoate Chemical compound CCCCCC(C(CC)C(C(=O)OC)(F)F)I UOGSCDCHYFXJCQ-UHFFFAOYSA-N 0.000 description 1
- GIKLJBLHEQHSTN-UHFFFAOYSA-N methyl 3-ethyl-2,2-difluoro-4-iodooctanoate Chemical compound CCCCC(C(CC)C(C(=O)OC)(F)F)I GIKLJBLHEQHSTN-UHFFFAOYSA-N 0.000 description 1
- FGJCMKSNWJYJED-UHFFFAOYSA-N methyl 3-ethyl-2,2-difluoro-4-iodotetradecanoate Chemical compound CCCCCCCCCCC(C(CC)C(C(=O)OC)(F)F)I FGJCMKSNWJYJED-UHFFFAOYSA-N 0.000 description 1
- MWEOVWPPNUDBPT-UHFFFAOYSA-N methyl 3-ethyl-2,2-difluoro-4-iodotridecanoate Chemical compound CCCCCCCCCC(C(CC)C(C(=O)OC)(F)F)I MWEOVWPPNUDBPT-UHFFFAOYSA-N 0.000 description 1
- RDOISSPGJZGUTG-UHFFFAOYSA-N methyl 4-ethyl-2,2-difluoro-4-iodohexanoate Chemical compound CCC(CC)(CC(C(=O)OC)(F)F)I RDOISSPGJZGUTG-UHFFFAOYSA-N 0.000 description 1
- JNJVZWSFFHUWFP-UHFFFAOYSA-N methyl 4-ethyl-2,2-difluoro-4-iodononanoate Chemical compound CCCCCC(CC)(CC(C(=O)OC)(F)F)I JNJVZWSFFHUWFP-UHFFFAOYSA-N 0.000 description 1
- IRXUVGOJGGUKDA-UHFFFAOYSA-N methyl dodec-3-enoate Chemical compound CCCCCCCCC=CCC(=O)OC IRXUVGOJGGUKDA-UHFFFAOYSA-N 0.000 description 1
- LFUAISXNEQSFSW-UHFFFAOYSA-N methyl tridec-3-enoate Chemical compound CCCCCCCCCC=CCC(=O)OC LFUAISXNEQSFSW-UHFFFAOYSA-N 0.000 description 1
- YZULHOOBWDXEOT-UHFFFAOYSA-N n,n-diethylpentan-1-amine Chemical compound CCCCCN(CC)CC YZULHOOBWDXEOT-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical compound CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- YCBSHDKATAPNIA-UHFFFAOYSA-N non-3-ene Chemical compound CCCCCC=CCC YCBSHDKATAPNIA-UHFFFAOYSA-N 0.000 description 1
- UMIPWJGWASORKV-UHFFFAOYSA-N oct-1-yne Chemical compound CCCCCCC#C UMIPWJGWASORKV-UHFFFAOYSA-N 0.000 description 1
- WXPWPYISTQCNDP-UHFFFAOYSA-N oct-7-en-1-ol Chemical compound OCCCCCCC=C WXPWPYISTQCNDP-UHFFFAOYSA-N 0.000 description 1
- ATCNYMVVGBLQMQ-UHFFFAOYSA-N oct-7-yn-1-ol Chemical compound OCCCCCCC#C ATCNYMVVGBLQMQ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- CRWVOXFUXPYTRK-UHFFFAOYSA-N pent-4-yn-1-ol Chemical compound OCCCC#C CRWVOXFUXPYTRK-UHFFFAOYSA-N 0.000 description 1
- UXPOJVLZTPGWFX-UHFFFAOYSA-N pentafluoroethyl iodide Chemical compound FC(F)(F)C(F)(F)I UXPOJVLZTPGWFX-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OMBXNSHDJUALCV-UHFFFAOYSA-N tridec-3-ene Chemical compound CCCCCCCCCC=CCC OMBXNSHDJUALCV-UHFFFAOYSA-N 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
本発明はオレフィン類又はアセチレン類にパーフルオロアルキルハライドをラジカル反応で付加させ、含フッ素化合物を製造する方法に関する。本発明の含フッ素化合物は、電子材料や医・農薬の製造中間体として有用な化合物である。 The present invention relates to a method for producing a fluorine-containing compound by radically adding a perfluoroalkyl halide to olefins or acetylenes. The fluorine-containing compound of the present invention is a compound useful as an intermediate for producing electronic materials, medicines and agricultural chemicals.
従来より、アクリル酸エステル誘導体にパーフルオロアルキルヨージドを、高圧水銀灯を用いた光反応により付加させα−ヨウド−β−パーフルオロアルキル付加体を得る方法が知られている(例えば、非特許文献1、非特許文献2、非特許文献3、非特許文献4参照)。
また、光増感剤を触媒として用い、可視光照射下、パーフルオロアルキルヨージド又はパーフルオロアルキルブロミドをオレフィン類へ付加させる方法が知られている(特許文献1〜3、非特許文献5参照)。
さらに、過剰のアミン類を用い、可視光照射下、パーフルオロアルキルヨージドをオレフィン類へ付加させる方法が知られている(非特許文献6参照)。
加えて、ラジカル開始剤を用い、加熱下、オレフィン類にパーフルオロヨージドをラジカル付加させる方法が知られている。
従来の非特許文献1、非特許文献2、非特許文献3及び非特許文献4に記載の方法は、高圧水銀灯を光源として用いているが、反応効率が悪く、高出力の光源で長時間反応させることが必要であり、さらに必要に応じて加熱条件下、反応を実施する必要がある等の課題があった。
一方、特許文献1、特許文献2、特許文献3、非特許文献5及び非特許文献6に記載の方法は、光増感剤としてエオシンYを触媒として用いる方法や大過剰のアミン類を用いる方法であるが、満足できる収率とは言い難い。
加えて、周知のラジカル開始剤を用いる方法は、加熱条件下の反応のため、用いる基質又は生成物が、熱的に分解する場合や、生成物がさらにラジカル付加するテロメリゼーション等の副反応を発生する場合がある等の課題がある。
Conventionally, a method has been known in which a perfluoroalkyl iodide is added to an acrylate derivative by a photoreaction using a high-pressure mercury lamp to obtain an α-iodo-β-perfluoroalkyl adduct (for example, Non-Patent Documents). 1, Non-Patent Document 2, Non-Patent Document 3, and Non-Patent Document 4).
Further, a method of adding a perfluoroalkyl iodide or perfluoroalkyl bromide to olefins under visible light irradiation using a photosensitizer is known (see Patent Documents 1 to 3 and Non-Patent Document 5). ).
Further, there is known a method of adding perfluoroalkyl iodide to olefins under irradiation of visible light using an excess of amines (see Non-Patent Document 6).
In addition, a method of radically adding perfluoroiodide to olefins under heating using a radical initiator is known.
The conventional methods described in Non-Patent Document 1, Non-Patent Document 2, Non-Patent Document 3, and Non-Patent Document 4 use a high-pressure mercury lamp as a light source, but the reaction efficiency is poor and a high-output light source reacts for a long time. However, there is a problem that the reaction needs to be carried out under heating conditions, if necessary.
On the other hand, the methods described in Patent Document 1, Patent Document 2, Patent Document 3, Non-Patent Document 5 and Non-Patent Document 6 are a method using Eosin Y as a photosensitizer as a catalyst and a method using a large excess of amines. However, it is hard to say that the yield is satisfactory.
In addition, the method using a well-known radical initiator is a reaction under heating conditions, and therefore, when a substrate or a product used is thermally decomposed or a side reaction such as telomerization in which the product is further radical-added. There are problems such as occurrence of.
本発明者らは、これら従来技術を鑑み、オレフィン類又はアセチレン類へのパーフルオロアルキルラジカル類の付加反応について、より工業的に実施可能な方法を提供することにある。 In view of these conventional techniques, the present inventors intend to provide a more industrially feasible method for the addition reaction of perfluoroalkyl radicals to olefins or acetylenes.
そこで、本発明者らは、光ラジカルによるオレフィン化合物へのパーフルオロアルキルラジカル類の付加反応について鋭意検討した結果、ある種のエナミン誘導体が蛍光ランプ等を光源として用いた光反応において、触媒活性が高いことを見出し、また、適用基質についても光増感剤としてエオシンY等を用いた場合に適用可能な末端オレフィン類やアセチレン類に限らず、内部オレフィンや電子不足オレフィンについてもパーフルオロアルキル基のラジカル付加反応が可能であることを見出した。さらにアミン類を添加することにより、オレフィン類又はアセチレン類に対して、エナミン誘導体が0.01モルでも良好な反応結果が得られることを見出し、本発明を完成させるに至った。 Therefore, as a result of diligent studies on the addition reaction of perfluoroalkyl radicals to olefin compounds by photoradicals, the present inventors have shown that certain enamine derivatives have a catalytic activity in a photoreaction using a fluorescent lamp or the like as a light source. It was found that it is high, and the applicable substrate is not limited to the terminal olefins and acetylenes applicable when Eosin Y or the like is used as the photosensitizer, but the internal olefin and electron-deficient olefin are It was found that radical addition reaction is possible. By further adding amines, it has been found that a good reaction result can be obtained even with 0.01 mol of an enamine derivative with respect to olefins or acetylenes, and the present invention has been completed.
すなわち本発明は、下記一般式(1)
下記一般式(2)
で表されるオレフィン類、
又は
下記一般式(3)
下記一般式(4)
R8−I (4)
(式(4)中、R8は、トリフルオロメチル基、ペンタフルオロエチル基、炭素数3〜8の直鎖若しくは分岐若しくは環式のパーフルオロアルキル基、メトキシカルボニルジフルオロメチル基又はエトキシカルボニルジフルオロメチル基を示す)で表される含フッ素有機ヨウ素化合物とを、
光照射下、反応させることを特徴とする、
下記一般式(5)
又は、
下記一般式(6)
で表わされる含フッ素化合物の製造方法を提供するものである。
That is, the present invention provides the following general formula (1)
The following general formula (2)
Olefins represented by
Or the following general formula (3)
The following general formula (4)
R 8 -I (4)
(In the formula (4), R 8 is a trifluoromethyl group, a pentafluoroethyl group, a linear or branched or cyclic perfluoroalkyl group having 3 to 8 carbon atoms, a methoxycarbonyldifluoromethyl group or an ethoxycarbonyldifluoromethyl group. And a fluorine-containing organic iodine compound represented by
Characterized by reacting under light irradiation,
The following general formula (5)
Or
The following general formula (6)
The present invention provides a method for producing a fluorine-containing compound represented by.
本発明により、様々なオレフィン類又はアセチレン類へパーフルオロアルキルラジカル及びハロゲンが付加した含フッ素化合物のより工業的製造方法を提供できる。 According to the present invention, it is possible to provide a more industrial method for producing a fluorine-containing compound in which a perfluoroalkyl radical and a halogen are added to various olefins or acetylenes.
以下、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明の一般式(1)で表されるエナミン誘導体としては、具体的には例えば、N−(2−メチル−3−フェニル−1−プロペン−1−イル)ピロリジン、N−(2−フェニル−1−プロペン−1−イル)ピロリジン、N−(2,2−ジフェニルエチレン−1−イル)ピロリジン、N−(2−フェニルエチレン−1−イル)ピロリジン、N−(2−メチル−3−フェニル−1−プロペン−1−イル)−(S)−2−[ビス(3,4−ジメトキシフェニル)メトキシメチル]ピロリジン、N−(2−フェニル−1−プロペン−1−イル)−(S)−2−[ビス(3,4−ジメトキシフェニル)メトキシメチル]ピロリジン、N−(2,2−ジフェニルエチレン−1−イル)−(S)−2−[ビス(3,4−ジメトキシフェニル)メトキシメチル]ピロリジン、N−(2−フェニルエチレン−1−イル)−(S)−2−[ビス(3,4−ジメトキシフェニル)メトキシメチル]ピロリジン等が挙げられる。 Specific examples of the enamine derivative represented by the general formula (1) of the present invention include N-(2-methyl-3-phenyl-1-propen-1-yl)pyrrolidine and N-(2-phenyl). -1-propen-1-yl)pyrrolidine, N-(2,2-diphenylethylene-1-yl)pyrrolidine, N-(2-phenylethylene-1-yl)pyrrolidine, N-(2-methyl-3-) Phenyl-1-propen-1-yl)-(S)-2-[bis(3,4-dimethoxyphenyl)methoxymethyl]pyrrolidine, N-(2-phenyl-1-propen-1-yl)-(S )-2-[Bis(3,4-dimethoxyphenyl)methoxymethyl]pyrrolidine, N-(2,2-diphenylethylene-1-yl)-(S)-2-[bis(3,4-dimethoxyphenyl) Examples thereof include methoxymethyl]pyrrolidine and N-(2-phenylethylene-1-yl)-(S)-2-[bis(3,4-dimethoxyphenyl)methoxymethyl]pyrrolidine.
本発明の一般式(2)で表されるオレフィン類で、R4が水素原子であるものとしては、具体的には例えば、エチレン、プロピレン、1−ブテン、1−ペンテン、1−ヘキセン、1−ヘプテン、1−オクテン、1−ノネン、1−デセン、1−ウンデセン、1−ドデセン、4−ヒドロキシ−1−ブテン、5−ヒドロキシ−1−ペンテン、6−ヒドロキシ−1−ヘキセン、7−ヒドロキシ−7−ヘプテン、8−ヒドロキシ−1−オクテン、スチレン、1,1−ジフェニルエチレン、アクリル酸メチル、アクリル酸エチル、アクリル酸(2−イソプロピルアダマンタン−2−イル)、アクリル酸(イソボルネン−2−イル)、メタクリル酸メチル、メタクリル酸エチル、メタクリル酸(2−イソプロピルアダマンタン−2−イル)、メタクリル酸(イソボルネン−2−イル)、2−メチルプロピレン、2−メチル−1−ブテン、2−メチル−1−ペンテン、2−メチル−1−ヘキセン、2−メチル−1−ヘプテン、2−メチル−1−オクテン、2−メチル−1−ノネン、2−メチル−1−デセン、2−メチル−1−ウンデセン、2−メチル−1−ドデセン、2−エチルプロピレン、2−エチル−1−ブテン、2−エチル−1−ペンテン、2−エチル−1−ヘキセン、2−エチル−1−ヘプテン、2−エチル−1−オクテン、2−エチル−1−ノネン、2−エチル−1−デセン、2−エチル−1−ウンデセン、2−エチル−1−ドデセン等が挙げられる。 Specific examples of the olefin represented by the general formula (2) of the present invention in which R 4 is a hydrogen atom include, for example, ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1 -Heptene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-dodecene, 4-hydroxy-1-butene, 5-hydroxy-1-pentene, 6-hydroxy-1-hexene, 7-hydroxy -7-heptene, 8-hydroxy-1-octene, styrene, 1,1-diphenylethylene, methyl acrylate, ethyl acrylate, acrylic acid (2-isopropyladamantan-2-yl), acrylic acid (isobornene-2- Yl), methyl methacrylate, ethyl methacrylate, methacrylic acid (2-isopropyladamantan-2-yl), methacrylic acid (isobornen-2-yl), 2-methylpropylene, 2-methyl-1-butene, 2-methyl -1-Pentene, 2-methyl-1-hexene, 2-methyl-1-heptene, 2-methyl-1-octene, 2-methyl-1-nonene, 2-methyl-1-decene, 2-methyl-1. -Undecene, 2-methyl-1-dodecene, 2-ethylpropylene, 2-ethyl-1-butene, 2-ethyl-1-pentene, 2-ethyl-1-hexene, 2-ethyl-1-heptene, 2- Ethyl-1-octene, 2-ethyl-1-nonene, 2-ethyl-1-decene, 2-ethyl-1-undecene, 2-ethyl-1-dodecene and the like can be mentioned.
本発明の一般式(2)で表されるオレフィン類で、R4が水素原子でないものとしては、具体的には例えば、2−ブテン、2−ペンテン、2−ヘキセン、2−ヘプテン、2−オクテン、2−ノネン、2−デセン、2−ウンデセン、2−ドデセン、2−トリデセン、3−ヘキセン、3−ヘプテン、3−オクテン、3−ノネン、3−デセン、3−ウンデセン、3−ドデセン、3−トリデセン、3−テトラデセン、シクロペンテン、シクロヘキセン、シクロヘプテン、シクロオクテン等が挙げられる。 Specific examples of the olefin represented by the general formula (2) of the present invention in which R 4 is not a hydrogen atom include, for example, 2-butene, 2-pentene, 2-hexene, 2-heptene, 2- Octene, 2-nonene, 2-decene, 2-undecene, 2-dodecene, 2-tridecene, 3-hexene, 3-heptene, 3-octene, 3-nonene, 3-decene, 3-undecene, 3-dodecene, 3-tridecene, 3-tetradecene, cyclopentene, cyclohexene, cycloheptene, cyclooctene and the like can be mentioned.
本発明の一般式(3)で表されるアセチレン類としては、具体的には例えば、1−オクチン、1−ノニン、1−デシン、1−ウンデシン、1−ドデシン、4−ヒドロキシ−1−ブチン、5−ヒドロキシ−1−ペンチン、6−ヒドロキシ−1−ヘキチン、7−ヒドロキシ−1−ヘプチン、8−ヒドロキシ−1−オクチン等が挙げられる。 Specific examples of the acetylenes represented by the general formula (3) of the present invention include 1-octyne, 1-nonine, 1-decine, 1-undecine, 1-dodecine, 4-hydroxy-1-butyne. , 5-hydroxy-1-pentyne, 6-hydroxy-1-hexyne, 7-hydroxy-1-heptin, 8-hydroxy-1-octyne and the like.
本発明の一般式(4)で表される含フッ素有機ヨウ素化合物としては、具体的には例えば、ヨードトリフルオロメタン、ヨードペンタフルオロエタン、1−ヨードヘプタフルオロプロパン、2−ヨードヘプタフルオロプロパン、1−ヨードノナフルオロブタン、2−ヨードノナフルオロブタン、1−ヨードウンデカフルオロペンタン、2−ヨードウンデカフルオロペンタン、ヨードノナフルオロシクロペンタン、1−ヨードトリデカフルオロヘキサン、ヨードウンデカフルオロシクロヘキサン、1−ヨードペンタデカフルオロヘプタン、1−ヨードヘプタデカフルオロオクタン、ヨードジフルオロ酢酸メチル、ヨードジフルオロ酢酸エチル等が挙げられる。 Specific examples of the fluorine-containing organic iodine compound represented by the general formula (4) of the present invention include iodotrifluoromethane, iodopentafluoroethane, 1-iodoheptafluoropropane, 2-iodoheptafluoropropane, 1 -Iodononafluorobutane, 2-iodononafluorobutane, 1-iodoundecafluoropentane, 2-iodoundecafluoropentane, iodononafluorocyclopentane, 1-iodotridecafluorohexane, iodoundecafluorocyclohexane, 1 -Iodopentadecafluoroheptane, 1-iodoheptadecafluorooctane, methyl iododifluoroacetate, ethyl iododifluoroacetate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4及びR5が水素原子、R6がメチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−ヨードブタン、1,1,1,2,2−ペンタフルオロ−4−ヨードペンタン、1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨードヘキサン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−ヨードペンタン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−ヨードヘプタン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−ヨードヘキサン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−ヨードオクタン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−ヨードヘプタン、1−(ノナフルオロシクロペンチル)−2−ヨードプロパン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードノナン、1−(ウンデカフルオロシクロヘキシル)−2−ヨードプロパン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−ヨードウンデカン、2,2−ジフルオロ−4−ヨードペンタン酸メチル、2,2−ジフルオロ−4−ヨードペンタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 and R 5 are hydrogen atoms and R 6 is a methyl group, include, for example, 1,1,1-tri Fluoro-3-iodobutane, 1,1,1,2,2-pentafluoro-4-iodopentane, 1,1,1,2,2,3,3-heptafluoro-5-iodohexane, 1,1, 1,2-Tetrafluoro-2-(trifluoromethyl)-4-iodopentane, 1,1,1,2,2,3,3,4,4-nonafluoro-6-iodoheptane, 1,1,1 ,2,2,3-Hexafluoro-3-(trifluoromethyl)-5-iodohexane, 1,1,1,2,2,3,3,4,5,5-undecafluoro-7 -Iodooctane, 1,1,1,2,2,3,3,4-octafluoro-4-(trifluoromethyl)-6-iodoheptane, 1-(nonafluorocyclopentyl)-2-iodopropane, 1 , 1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodononane, 1-(undecafluorocyclohexyl)-2-iodopropane, 1,1 , 1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-iododecane, 1,1,1,2,2,3,3,4 ,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-iodoundecane, methyl 2,2-difluoro-4-iodopentanoate, 2,2-difluoro-4-iodo Examples include ethyl pentanoate and the like.
本発明の一般式(5)で表される含フッ素化合物で、R4及びR5が水素原子、R6がエチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−ヨードペンタン、1,1,1,2,2−ペンタフルオロ−4−ヨードヘキサン、1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨードヘプタン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−ヨードヘキサン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−ヨードオクタン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−ヨードノナン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−ヨードオクタン、1−(ノナフルオロシクロペンチル)−2−ヨードブタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードデカン、1−(ウンデカフルオロシクロヘキシル)−2−ヨードブタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−ヨードドデカン、2,2−ジフルオロ−4−ヨードヘキサン酸メチル、2,2−ジフルオロ−4−ヨードヘキサン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 and R 5 are hydrogen atoms and R 6 is an ethyl group, include 1,1,1-tri Fluoro-3-iodopentane, 1,1,1,2,2-pentafluoro-4-iodohexane, 1,1,1,2,2,3,3-heptafluoro-5-iodoheptane, 1,1 ,1,2-Tetrafluoro-2-(trifluoromethyl)-4-iodohexane, 1,1,1,2,2,3,3,4,4-nonafluoro-6-iodooctane, 1,1, 1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-iodoheptane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro- 7-iodononane, 1,1,1,2,2,3,3,4-octafluoro-4-(trifluoromethyl)-6-iodooctane, 1-(nonafluorocyclopentyl)-2-iodobutane, 1, 1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iododecane, 1-(undecafluorocyclohexyl)-2-iodobutane, 1,1,1 , 2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-iodoundecane, 1,1,1,2,2,3,3,4 4,5,5,6,6,7,7,8,8-heptadecafluoro-10-iodododecane, methyl 2,2-difluoro-4-iodohexanoate, 2,2-difluoro-4-iodohexane Ethyl acid and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4及びR5が水素原子、R6が炭素数3〜10の直鎖アルキル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−ヨードヘキサン、1,1,1,2,2−ペンタフルオロ−4−ヨードヘプタン、1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードウンデカン、1,1,1−トリフルオロ−3−ヨードヘプタン、1,1,1,2,2−ペンタフルオロ−4−ヨードオクタン、1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードドデカン、1,1,1−トリフルオロ−3−ヨードオクタン、1,1,1,2,2−ペンタフルオロ−4−ヨードノナン、1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードトリデカン、1,1,1−トリフルオロ−3−ヨードノナン、1,1,1,2,2−ペンタフルオロ−4−ヨードデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードテトラデカン、1,1,1−トリフルオロ−3−ヨードデカン、1,1,1,2,2−ペンタフルオロ−4−ヨードウンデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードペンタデカン、1,1,1−トリフルオロ−3−ヨードウンデカン、1,1,1,2,2−ペンタフルオロ−4−ヨードドデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−ヨードヘプタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタフルオロ−10−ヨードオクタデカン、1,1,1−トリフルオロ−3−ヨードドデカン、1,1,1,2,2−ペンタフルオロ−4−ヨードトリデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨードテトラデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−ヨードテトラデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘプタデカン、1,1,1−トリフルオロ−3−ヨードトリデカン、1,1,1,2,2−ペンタフルオロ−4−ヨードテトラデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨードペンタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードオクタデカン等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, wherein R 4 and R 5 are hydrogen atoms and R 6 is a linear alkyl group having 3 to 10 carbon atoms, include, for example, , 1,1,1-trifluoro-3-iodohexane, 1,1,1,2,2-pentafluoro-4-iodoheptane, 1,1,1,2,2,3,3-heptafluoro- 5-iodooctane, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodoundecane, 1,1,1-trifluoro-3 -Iodoheptane, 1,1,1,2,2-pentafluoro-4-iodooctane, 1,1,1,2,2,3,3-heptafluoro-5-iodononane, 1,1,1,2 , 2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodododecane, 1,1,1-trifluoro-3-iodooctane, 1,1,1,2, 2-pentafluoro-4-iodononane, 1,1,1,2,2,3,3-heptafluoro-5-iododecane, 1,1,1,2,2,3,3,4,4,5 5,6,6-tridecafluoro-8-iodotridecane, 1,1,1-trifluoro-3-iodononane, 1,1,1,2,2-pentafluoro-4-iododecane, 1,1, 1,2,2,3,3-heptafluoro-5-iodoundecane, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8- Iodotetradecane, 1,1,1-trifluoro-3-iododecane, 1,1,1,2,2-pentafluoro-4-iodoundecane, 1,1,1,2,2,3,3-heptafluoro -5-iodododecane, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodopentadecane, 1,1,1-trifluoro- 3-iodoundecane, 1,1,1,2,2-pentafluoro-4-iodododecane, 1,1,1,2,2,3,3-heptafluoro-5-iodotridecane, 1,1, 1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane, 1,1,1,2,2,3,3,4,4,5 , 5,6,6,7,7-pentadecafluoro-9-iodoheptadecane, 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7 ,8,8-Heptafluoro-10-iodooctadecane, 1,1,1-trifluoro-3-iodododecane, 1,1,1,2,2-pentafluoro-4 -Iodotridecane, 1,1,1,2,2,3,3-heptafluoro-5-iodotetradecane, 1,1,1,2,2,3,3,4,4-nonafluoro-6-iodo Tetradecane, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodoheptadecane, 1,1,1-trifluoro-3-iodo Tridecane, 1,1,1,2,2-pentafluoro-4-iodotetradecane, 1,1,1,2,2,3,3-heptafluoro-5-iodopentadecane, 1,1,1,2 , 2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodooctadecane and the like.
本発明の一般式(5)で表される含フッ素化合物で、R4及びR5が水素原子、R6が末端に水酸基を有する炭素数2〜6のアルキル基である化合物としては、具体的には例えば、5,5,5−トリフルオロ−3−ヨード−1−ペンタノール、5,5,6,6,6−ペンタフルオロ−3−ヨード−1−ヘキサノール、5,5,6,6,7,7,7−ヘプタフルオロ−3−ヨード−1−ヘプタノール、5,5,6,6,7,7,8,8,9,9,10,10,10−トリデカフルオロ−3−ヨード−1−デカノール、6,6,6−トリフルオロ−4−ヨード−1−ヘキサノール、6,6,7,7,7−ペンタフルオロ−4−ヨード−1−ヘプタノール、6,6,7,7,8,8,8−ヘプタフルオロ−4−ヨード−1−オクタノール、6,6,7,7,8,8,9,9,10.10,11,11,11−トリデカフルオロ−4−ヨード−1−ウンデカノール、7,7,7−トリフルオロ−5−ヨード−1−ヘプタノール、7,7,8,8,8−ペンタフルオロ−5−ヨード−1−オクタノール、7,7,8,8,9,9,9−ヘプタフルオロ−5−ヨード−1−ノナノール、7,7,8,8,9,9,10,10,11,11,12,12,12−トリデカフルオロ−5−ヨード−1−ドデカノール、8,8,8−トリフルオロ−6−ヨード−1−オクタノール、8,8,9,9,9−ペンタフルオロ−6−ヨード−1−ノナノール、8,8,9,9,10,10,10−ヘプタフルオロ−6−ヨード−1−デカノール、8,8,9,9,10,10,11,11,12,12,13,13,13−トリデカフルオロ−6−ヨード−1−トリデカノール、9,9,9−トリフルオロ−7−ヨード−1−ノナノール、9,9,10,10,10−ペンタフルオロ−7−ヨード−1−デカノール、9,9,10,10,11,11,11−ヘプタフルオロ−7−ヨード−1−ウンデカノール、9,9,10,10,11,11,12,12,13,13,14,14,14−トリデカフルオロ−7−ヨード−1−ペンタデカノール等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 and R 5 are hydrogen atoms, and R 6 is a C 2-6 alkyl group having a hydroxyl group at the terminal, Include, for example, 5,5,5-trifluoro-3-iodo-1-pentanol, 5,5,6,6,6-pentafluoro-3-iodo-1-hexanol, 5,5,6,6. , 7,7,7-Heptafluoro-3-iodo-1-heptanol, 5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluoro-3- Iodo-1-decanol, 6,6,6-trifluoro-4-iodo-1-hexanol, 6,6,7,7,7-pentafluoro-4-iodo-1-heptanol, 6,6,7, 7,8,8,8-Heptafluoro-4-iodo-1-octanol, 6,6,7,7,8,8,9,9,10.10,11,11,11-tridecafluoro-4 -Iodo-1-undecanol, 7,7,7-trifluoro-5-iodo-1-heptanol, 7,7,8,8,8-pentafluoro-5-iodo-1-octanol, 7,7,8 , 8,9,9,9-heptafluoro-5-iodo-1-nonanol, 7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluoro- 5-iodo-1-dodecanol, 8,8,8-trifluoro-6-iodo-1-octanol, 8,8,9,9,9-pentafluoro-6-iodo-1-nonanol, 8,8, 9,9,10,10,10-Heptafluoro-6-iodo-1-decanol, 8,8,9,9,10,10,11,11,12,12,13,13,13-tridecafluoro -6-iodo-1-tridecanol, 9,9,9-trifluoro-7-iodo-1-nonanol, 9,9,10,10,10-pentafluoro-7-iodo-1-decanol, 9,9 , 10,10,11,11,11-Heptafluoro-7-iodo-1-undecanol, 9,9,10,10,11,11,12,12,13,13,14,14,14-trideca Fluoro-7-iodo-1-pentadecanol and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4及びR5が水素原子、R6がフェニル基である化合物としては、具体的には例えば、3,3,3−トリフルオロ−1−フェニル−1−ヨードプロパン、3,3,4,4,4−ペンタフルオロ−1−フェニル−1−ヨードブタン、3,3,4,4,5,5,5−ヘプタフルオロ−1−フェニル−1−ヨードペンタン、3,4,4,4−テトラフルオロ−3−(トリフルオロメチル)−1−フェニル−1−ヨードブタン、3.3,4,4,5,5,6,6,6−ノナフルオロ−1−フェニル−1−ヨードヘキサン、3,4,4,5,5,5−ヘキサフルオロ−3−(トリフルオロメチル)−1−フェニル−1−ヨードヘキサン、3,3,4,4,5,5,6,6,7,7,7−ウンデカフルオロ−1−フェニル−1−ヨードヘプタン、3,4,4,5,5,6,6,6−オクタフルオロ−3−(トリフルオロメチル)−1−フェニル−1−ヨードヘキサン、2−(ノナフルオロシクロペンチル)−1−フェニル−1−ヨードエタン、3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−1−フェニル−1−ヨードオクタン、3−(ウンデカフルオロシクロヘキシル)−1−フェニル−1−ヨードエタン、3,3,4,4,5,5,6,6,7,7,8,8,9,9,9−ペンタデカフルオロ−1−フェニル−1−ヨードノナン、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ヘプタデカフルオロ−1−フェニル−1−ヨードデカン、2,2−ジフルオロ−4−フェニル−4−ヨードブタン酸メチル、2,2−ジフルオロ−4−フェニル−4−ヨードブタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention in which R 4 and R 5 are hydrogen atoms and R 6 is a phenyl group include, for example, 3,3,3-tri Fluoro-1-phenyl-1-iodopropane, 3,3,4,4,4-pentafluoro-1-phenyl-1-iodobutane, 3,3,4,4,5,5,5-heptafluoro-1 -Phenyl-1-iodopentane, 3,4,4,4-tetrafluoro-3-(trifluoromethyl)-1-phenyl-1-iodobutane, 3.3,4,4,5,5,6,6 ,6-Nonafluoro-1-phenyl-1-iodohexane, 3,4,4,5,5,5-hexafluoro-3-(trifluoromethyl)-1-phenyl-1-iodohexane, 3,3,3 4,4,5,5,6,6,7,7,7-undecafluoro-1-phenyl-1-iodoheptane, 3,4,4,5,5,6,6,6-octafluoro- 3-(trifluoromethyl)-1-phenyl-1-iodohexane, 2-(nonafluorocyclopentyl)-1-phenyl-1-iodoethane, 3,3,4,4,5,5,6,6,7 , 7,8,8,8-Tridecafluoro-1-phenyl-1-iodooctane, 3-(undecafluorocyclohexyl)-1-phenyl-1-iodoethane, 3,3,4,4,5,5 , 6,6,7,7,8,8,9,9,9-pentadecafluoro-1-phenyl-1-iodononane, 3,3,4,4,5,5,6,6,7,7 , 8,8,9,9,10,10,10-Heptadecafluoro-1-phenyl-1-iododecane, methyl 2,2-difluoro-4-phenyl-4-iodobutanoate, 2,2-difluoro-4 -Phenyl-4-iodobutanoic acid ethyl etc. are mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4及びR5が水素原子、R6がメトキシカルボニル基である化合物としては、具体的には例えば、4,4,4−トリフルオロ−2−ヨードブタン酸メチル、4,4,5,5,5−ペンタフルオロ−2−ヨードペンタン酸メチル、4,4,5,5,6,6,6−ヘプタフルオロ−2−ヨードヘキサン酸メチル、4,5,5,5−テトラフルオロ−4−(トリフルオロメチル)−2−ヨードペンタン酸メチル、4,4,5,5,6,6,7,7,7−ノナフルオロ−2−ヨードヘプタン酸メチル、4,5,5,6,6,6−ヘキサフルオロ−4−(トリフルオロメチル)−2−ヨードヘキサン酸メチル、4,4,5,5,6,6,7,7,8,8,8−ウンデカフルオロ−2−ヨードオクタン酸メチル、4,5,5,6,6,7,7,7−オクタフルオロ−3−(トリフルオロメチル)−2−ヨードヘプタン酸メチル、3−(ノナフルオロシクロペンチル)−2−ヨードプロピオン酸メチル、4,4,5,5,6,6,7,7,8,8,9,9,9−トリデカフルオロ−2−ヨードノナン酸メチル、3−(ウンデカフルオロシクロヘキシル)−2−ヨードプロピオン酸メチル、4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ペンタデカフルオロ−2−ヨードデカン酸メチル、4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11−ヘプタデカフルオロ−2−ヨードウンデカン酸メチル、2,2−ジフルオロ−4−(メトキシカルボニル)−4−ヨードブタン酸メチル、2,2−ジフルオロ−4−(メトキシカルボニル)−4−ヨードブタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, wherein R 4 and R 5 are hydrogen atoms and R 6 is a methoxycarbonyl group, include, for example, 4,4,4- Methyl trifluoro-2-iodobutanoate, 4,4,5,5,5-pentafluoro-2-iodopentanoate methyl, 4,4,5,5,6,6,6-heptafluoro-2-iodohexane Methyl acid, 4,5,5,5-tetrafluoro-4-(trifluoromethyl)-2-methyl iodopentanoate, 4,4,5,5,6,6,7,7,7-Nonafluoro-2 -Methyl iodoheptanoate, 4,5,5,6,6,6-methyl hexafluoro-4-(trifluoromethyl)-2-methyl iodohexanoate, 4,4,5,5,6,6,7, Methyl 7,8,8,8-undecafluoro-2-iodooctanoate, 4,5,5,6,6,7,7,7-octafluoro-3-(trifluoromethyl)-2-iodoheptane Methyl acid, methyl 3-(nonafluorocyclopentyl)-2-iodopropionate, 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2- Methyl iodononanoate, Methyl 3-(undecafluorocyclohexyl)-2-iodopropionate, 4,4,5,5,6,6,7,7,8,8,9,9,10,10,10- Methyl pentadecafluoro-2-iododecanoate, 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2- Examples thereof include methyl iodoundecanoate, methyl 2,2-difluoro-4-(methoxycarbonyl)-4-iodobutanoate and ethyl 2,2-difluoro-4-(methoxycarbonyl)-4-iodobutanoate.
本発明の一般式(5)で表される含フッ素化合物で、R4及びR5が水素原子、R6がエトキシカルボニル基である化合物としては、具体的には例えば、4,4,4−トリフルオロ−2−ヨードブタン酸エチル、4,4,5,5,5−ペンタフルオロ−2−ヨードペンタン酸エチル、4,4,5,5,6,6,6−ヘプタフルオロ−2−ヨードヘキサン酸エチル、4,5,5,5−テトラフルオロ−4−(トリフルオロメチル)−2−ヨードペンタン酸エチル、4,4,5,5,6,6,7,7,7−ノナフルオロ−2−ヨードヘプタン酸エチル、4,5,5,6,6,6−ヘキサフルオロ−4−(トリフルオロメチル)−2−ヨードヘキサン酸エチル、4,4,5,5,6,6,7,7,8,8,8−ウンデカフルオロ−2−ヨードオクタン酸エチル、4,5,5,6,6,7,7,7−オクタフルオロ−3−(トリフルオロメチル)−2−ヨードヘプタン酸エチル、3−(ノナフルオロシクロペンチル)−2−ヨードプロピオン酸エチル、4,4,5,5,6,6,7,7,8,8,9,9,9−トリデカフルオロ−2−ヨードノナン酸エチル、3−(ウンデカフルオロシクロヘキシル)−2−ヨードプロピオン酸エチル、4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ペンタデカフルオロ−2−ヨードデカン酸エチル、4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11−ヘプタデカフルオロ−2−ヨードウンデカン酸エチル、2,2−ジフルオロ−4−(エトキシカルボニル)−4−ヨードブタン酸メチル、2,2−ジフルオロ−4−(エトキシカルボニル)−4−ヨードブタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, wherein R 4 and R 5 are hydrogen atoms and R 6 is an ethoxycarbonyl group, include, for example, 4,4,4- Ethyl trifluoro-2-iodobutanoate, 4,4,5,5,5-pentafluoro-2-iodopentanoate, 4,4,5,5,6,6,6-heptafluoro-2-iodohexane Ethyl acid salt, 4,5,5,5-tetrafluoro-4-(trifluoromethyl)-2-iodopentanoic acid ethyl salt, 4,4,5,5,6,6,7,7,7-nonafluoro-2 -Ethyl iodoheptanoate, 4,5,5,6,6,6-ethyl hexafluoro-4-(trifluoromethyl)-2-ethyl iodohexanoate, 4,4,5,5,6,6,7, Ethyl 7,8,8,8-undecafluoro-2-iodooctanoate, 4,5,5,6,6,7,7,7-octafluoro-3-(trifluoromethyl)-2-iodoheptane Ethyl acid, ethyl 3-(nonafluorocyclopentyl)-2-iodopropionate, 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2- Ethyl iodononanoate, 3-(undecafluorocyclohexyl)-2-ethyl iodopropionate, 4,4,5,5,6,6,7,7,8,8,9,9,10,10,10- Ethyl pentadecafluoro-2-iododecanoate, 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2- Examples thereof include ethyl iodoundecanoate, methyl 2,2-difluoro-4-(ethoxycarbonyl)-4-iodobutanoate, and ethyl 2,2-difluoro-4-(ethoxycarbonyl)-4-iodobutanoate.
本発明の一般式(5)で表される含フッ素化合物で、R4及びR5が水素原子、R6が2−イソプロピルアダマンタン−2−イルオキシカルボニル基である化合物としては、具体的には例えば、4,4,4−トリフルオロ−2−ヨードブタン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,5−ペンタフルオロ−2−ヨードペンタン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,6,6,6−ヘプタフルオロ−2−ヨードヘキサン酸(2−イソプロピルアダマンタン−2−イル)、4,5,5,5−テトラフルオロ−4−(トリフルオロメチル)−2−ヨードペンタン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,6,6,7,7,7−ノナフルオロ−2−ヨードヘプタン酸(2−イソプロピルアダマンタン−2−イル)、4,5,5,6,6,6−ヘキサフルオロ−4−(トリフルオロメチル)−2−ヨードヘキサン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,6,6,7,7,8,8,8−ウンデカフルオロ−2−ヨードオクタン酸(2−イソプロピルアダマンタン−2−イル)、4,5,5,6,6,7,7,7−オクタフルオロ−3−(トリフルオロメチル)−2−ヨードヘプタン酸(2−イソプロピルアダマンタン−2−イル)、3−(ノナフルオロシクロペンチル)−2−ヨードプロピオン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,6,6,7,7,8,8,9,9,9−トリデカフルオロ−2−ヨードノナン酸(2−イソプロピルアダマンタン−2−イル)、3−(ウンデカフルオロシクロヘキシル)−2−ヨードプロピオン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ペンタデカフルオロ−2−ヨードデカン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11−ヘプタデカフルオロ−2−ヨードウンデカン酸(2−イソプロピルアダマンタン−2−イル)、2,2−ジフルオロ−4−[(2−イソプロピルアダマンタン−2−イル)オキシカルボニル]−4−ヨードブタン酸メチル、2,2−ジフルオロ−4−[(2−イソプロピルアダマンタン−2−イル)オキシカルボニル]−4−ヨードブタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 and R 5 are hydrogen atoms and R 6 is a 2-isopropyladamantan-2-yloxycarbonyl group, For example, 4,4,4-trifluoro-2-iodobutanoic acid (2-isopropyladamantan-2-yl), 4,4,5,5,5-pentafluoro-2-iodopentanoic acid (2-isopropyladamantane- 2-yl), 4,5,5,5,6,6,6-heptafluoro-2-iodohexanoic acid (2-isopropyladamantan-2-yl), 4,5,5,5-tetrafluoro-4 -(Trifluoromethyl)-2-iodopentanoic acid (2-isopropyladamantan-2-yl), 4,4,5,5,6,6,7,7,7-nonafluoro-2-iodoheptanoic acid (2 -Isopropyladamantan-2-yl), 4,5,5,6,6,6-hexafluoro-4-(trifluoromethyl)-2-iodohexanoic acid (2-isopropyladamantan-2-yl), 4, 4,5,5,6,6,7,7,8,8,8-undecafluoro-2-iodooctanoic acid (2-isopropyladamantan-2-yl), 4,5,5,6,6 7,7,7-Octafluoro-3-(trifluoromethyl)-2-iodoheptanoic acid (2-isopropyladamantan-2-yl), 3-(nonafluorocyclopentyl)-2-iodopropionic acid (2-isopropyl Adamantan-2-yl), 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodononanoic acid (2-isopropyladamantan-2-yl) ), 3-(undecafluorocyclohexyl)-2-iodopropionic acid (2-isopropyladamantan-2-yl), 4,4,5,5,6,6,7,7,8,8,9,9 , 10,10,10-pentadecafluoro-2-iododecanoic acid (2-isopropyladamantan-2-yl), 4,4,5,5,6,6,7,7,8,8,9,9, 10,10,11,11,11-Heptadecafluoro-2-iodoundecanoic acid (2-isopropyladamantan-2-yl), 2,2-difluoro-4-[(2-isopropyladamantan-2-yl)oxy Carbonyl]-4-iodobutanoate, ethyl 2,2-difluoro-4-[(2-isopropyladamantan-2-yl)oxycarbonyl]-4-iodobutanoate, and the like. Be done.
本発明の一般式(5)で表される含フッ素化合物で、R4及びR5が水素原子、R6がイソボルネン−2−イルオキシカルボニル基である化合物としては、具体的には例えば、4,4,4−トリフルオロ−2−ヨードブタン酸(イソボルネン−2−イル)、4,4,5,5,5−ペンタフルオロ−2−ヨードペンタン酸(イソボルネン−2−イル)、4,4,5,5,6,6,6−ヘプタフルオロ−2−ヨードヘキサン酸(イソボルネン−2−イル)、4,5,5,5−テトラフルオロ−4−(トリフルオロメチル)−2−ヨードペンタン酸(イソボルネン−2−イル)、4,4,5,5,6,6,7,7,7−ノナフルオロ−2−ヨードヘプタン酸(イソボルネン−2−イル)、4,5,5,6,6,6−ヘキサフルオロ−4−(トリフルオロメチル)−2−ヨードヘキサン酸(イソボルネン−2−イル)、4,4,5,5,6,6,7,7,8,8,8−ウンデカフルオロ−2−ヨードオクタン酸(イソボルネン−2−イル)、4,5,5,6,6,7,7,7−オクタフルオロ−3−(トリフルオロメチル)−2−ヨードヘプタン酸(イソボルネン−2−イル)、3−(ノナフルオロシクロペンチル)−2−ヨードプロピオン酸(イソボルネン−2−イル)、4,4,5,5,6,6,7,7,8,8,9,9,9−トリデカフルオロ−2−ヨードノナン酸(イソボルネン−2−イル)、3−(ウンデカフルオロシクロヘキシル)−2−ヨードプロピオン酸(イソボルネン−2−イル)、4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ペンタデカフルオロ−2−ヨードデカン酸(イソボルネン−2−イル)、4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11−ヘプタデカフルオロ−2−ヨードウンデカン酸(イソボルネン−2−イル)、2,2−ジフルオロ−4−[(イソボルネン−2−イル)オキシカルボニル]−4−ヨードブタン酸メチル、2,2−ジフルオロ−4−[(イソボルネン−2−イル)オキシカルボニル]−4−ヨードブタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 and R 5 are hydrogen atoms and R 6 is an isobornen-2-yloxycarbonyl group, include: ,4,4-Trifluoro-2-iodobutanoic acid (isobornen-2-yl), 4,4,5,5,5-pentafluoro-2-iodopentanoic acid (isobornen-2-yl), 4,4 5,5,6,6,6-heptafluoro-2-iodohexanoic acid (isobornen-2-yl), 4,5,5,5-tetrafluoro-4-(trifluoromethyl)-2-iodopentanoic acid (Isobornen-2-yl), 4,4,5,5,6,6,7,7,7-nonafluoro-2-iodoheptanoic acid (isobornen-2-yl), 4,5,5,6,6 ,6-hexafluoro-4-(trifluoromethyl)-2-iodohexanoic acid (isobornen-2-yl), 4,4,5,5,6,6,7,7,8,8,8-un Decafluoro-2-iodooctanoic acid (isobornen-2-yl), 4,5,5,6,6,7,7,7-octafluoro-3-(trifluoromethyl)-2-iodoheptanoic acid (isobornene 2-yl), 3-(nonafluorocyclopentyl)-2-iodopropionic acid (isobornen-2-yl), 4,4,5,5,6,6,7,7,8,8,9,9 , 9-Tridecafluoro-2-iodononanoic acid (isobornen-2-yl), 3-(undecafluorocyclohexyl)-2-iodopropionic acid (isobornen-2-yl), 4,4,5,5,6 , 6,7,7,8,8,9,9,10,10,10-pentadecafluoro-2-iododecanoic acid (isobornen-2-yl), 4,4,5,5,6,6,7 , 7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-iodoundecanoic acid (isobornen-2-yl), 2,2-difluoro-4-[(isobornene- 2-yl)oxycarbonyl]-4-iodobutanoic acid methyl ester, 2,2-difluoro-4-[(isobornen-2-yl)oxycarbonyl]-4-iodobutanoic acid ethyl ester and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5及びR6がメチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−メチル−3−ヨードブタン、1,1,1,2,2−ペンタフルオロ−4−メチル−4−ヨードペンタン、1,1,1,2,2,3,3−ヘプタフルオロ−5−メチル−5−ヨードヘキサン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−メチル−4−ヨードペンタン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−メチル−6−ヨードヘプタン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−メチル−5−ヨードヘキサン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−メチル−7−ヨードオクタン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−メチル−6−ヨードヘプタン、1−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードプロパン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−メチル−8−ヨードノナン、1−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードプロパン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−メチル−9−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−メチル−10−ヨードウンデカン、2,2−ジフルオロ−4−メチル−4−ヨードペンタン酸メチル、2,2−ジフルオロ−4−メチル−4−ヨードペンタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention in which R 4 is a hydrogen atom and R 5 and R 6 are methyl groups include, for example, 1,1,1-tri Fluoro-3-methyl-3-iodobutane, 1,1,1,2,2-pentafluoro-4-methyl-4-iodopentane, 1,1,1,2,2,3,3-heptafluoro-5 -Methyl-5-iodohexane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-methyl-4-iodopentane, 1,1,1,2,2,3,3,3 4,4-nonafluoro-6-methyl-6-iodoheptane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-methyl-5-iodohexane, 1,1 ,1,2,2,3,3,4,4,5,5-undecafluoro-7-methyl-7-iodooctane, 1,1,1,2,2,3,3,4-octafluoro -4-(trifluoromethyl)-6-methyl-6-iodoheptane, 1-(nonafluorocyclopentyl)-2-methyl-2-iodopropane, 1,1,1,2,2,3,3,4 , 4,5,5,6,6-Tridecafluoro-8-methyl-8-iodononane, 1-(undecafluorocyclohexyl)-2-methyl-2-iodopropane, 1,1,1,2,2 , 3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-methyl-9-iododecane, 1,1,1,2,2,3,3,4,4 , 5,5,6,6,7,7,8,8-Heptadecafluoro-10-methyl-10-iodoundecane, 2,2-difluoro-4-methyl-4-iodopentanoate methyl, 2,2 -Ethyl difluoro-4-methyl-4-iodopentanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がエチル基、R6がメチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−メチル−3−ヨードペンタン、1,1,1,2,2−ペンタフルオロ−4−メチル−4−ヨードヘキサン、1,1,1,2,2,3,3−ヘプタフルオロ−5−メチル−5−ヨードヘプタン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−メチル−4−ヨードヘキサン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−メチル−6−ヨードオクタン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−メチル−5−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−メチル−7−ヨードノナン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−メチル−6−ヨードオクタン、1−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードブタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−メチル−8−ヨードデカン、1−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードブタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−メチル−9−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−メチル−10−ヨードドデカン、2,2−ジフルオロ−4−メチル−4−ヨードヘキサン酸メチル、2,2−ジフルオロ−4−メチル−4−ヨードヘキサン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an ethyl group, and R 6 is a methyl group, include: 1-trifluoro-3-methyl-3-iodopentane, 1,1,1,2,2-pentafluoro-4-methyl-4-iodohexane, 1,1,1,2,2,3,3- Heptafluoro-5-methyl-5-iodoheptane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-methyl-4-iodohexane, 1,1,1,2,2 3,3,4,4-Nonafluoro-6-methyl-6-iodooctane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-methyl-5-iodoheptane , 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-methyl-7-iodononane, 1,1,1,2,2,3,3,4 -Octafluoro-4-(trifluoromethyl)-6-methyl-6-iodooctane, 1-(nonafluorocyclopentyl)-2-methyl-2-iodobutane, 1,1,1,2,2,3,3 , 4,4,5,5,6,6-tridecafluoro-8-methyl-8-iododecane, 1-(undecafluorocyclohexyl)-2-methyl-2-iodobutane, 1,1,1,2, 2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-methyl-9-iodoundecane, 1,1,1,2,2,3,3,4 , 4,5,5,6,6,7,7,8,8-heptadecafluoro-10-methyl-10-iodododecane, methyl 2,2-difluoro-4-methyl-4-iodohexanoate, 2 , Ethyl 2-difluoro-4-methyl-4-iodohexanoate and the like.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−プロピル基、R6がメチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−メチル−3−ヨードヘキサン、1,1,1,2,2−ペンタフルオロ−4−メチル−4−ヨードヘプタン、1,1,1,2,2,3,3−ヘプタフルオロ−5−メチル−5−ヨードオクタン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−メチル−4−ヨードヘプタン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−メチル−6−ヨードノナン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−メチル−5−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−メチル−7−ヨードデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−メチル−6−ヨードノナン、1−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードペンタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−メチル−8−ヨードウンデカン、1−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードペンタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−メチル−9−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−メチル−10−ヨードトリデカン、2,2−ジフルオロ−4−メチル−4−ヨードヘプタン酸メチル、2,2−ジフルオロ−4−メチル−4−ヨードヘプタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-propyl group, and R 6 is a methyl group, include: 1,1-trifluoro-3-methyl-3-iodohexane, 1,1,1,2,2-pentafluoro-4-methyl-4-iodoheptane, 1,1,1,2,2,3, 3-heptafluoro-5-methyl-5-iodooctane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-methyl-4-iodoheptane, 1,1,1,2, 2,3,3,4,4-nonafluoro-6-methyl-6-iodononane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-methyl-5-iodo Octane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-methyl-7-iododecane, 1,1,1,2,2,3,3,3 4-Octafluoro-4-(trifluoromethyl)-6-methyl-6-iodononane, 1-(nonafluorocyclopentyl)-2-methyl-2-iodopentane, 1,1,1,2,2,3,3 3,4,4,5,5,6,6-tridecafluoro-8-methyl-8-iodoundecane, 1-(undecafluorocyclohexyl)-2-methyl-2-iodopentane, 1,1,1 , 2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-methyl-9-iodododecane, 1,1,1,2,2,3, 3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-methyl-10-iodotridecane, 2,2-difluoro-4-methyl-4-iodoheptane Methyl acid, ethyl 2,2-difluoro-4-methyl-4-iodoheptanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−ブチル基、R6がメチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−メチル−3−ヨードヘプタン、1,1,1,2,2−ペンタフルオロ−4−メチル−4−ヨードオクタン、1,1,1,2,2,3,3−ヘプタフルオロ−5−メチル−5−ヨードノナン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−メチル−4−ヨードオクタン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−メチル−6−ヨードデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−メチル−5−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−メチル−7−ヨードウンデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−メチル−6−ヨードデカン、1−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードヘキサン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−メチル−8−ヨードドデカン、1−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードヘキサン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−メチル−9−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−メチル−10−ヨードテトラデカン、2,2−ジフルオロ−4−メチル−4−ヨードオクタン酸メチル、2,2−ジフルオロ−4−メチル−4−ヨードオクタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-butyl group, and R 6 is a methyl group, include: 1,1-trifluoro-3-methyl-3-iodoheptane, 1,1,1,2,2-pentafluoro-4-methyl-4-iodooctane, 1,1,1,2,2,3, 3-heptafluoro-5-methyl-5-iodononane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-methyl-4-iodooctane, 1,1,1,2,2 , 3,3,4,4-Nonafluoro-6-methyl-6-iododecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-methyl-5-iodononane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-methyl-7-iodoundecane, 1,1,1,2,2,3,3,4 -Octafluoro-4-(trifluoromethyl)-6-methyl-6-iododecane, 1-(nonafluorocyclopentyl)-2-methyl-2-iodohexane, 1,1,1,2,2,3,3 , 4,4,5,5,6,6-tridecafluoro-8-methyl-8-iodododecane, 1-(undecafluorocyclohexyl)-2-methyl-2-iodohexane, 1,1,1, 2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-methyl-9-iodotridecane, 1,1,1,2,2,3,3 3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-methyl-10-iodotetradecane, 2,2-difluoro-4-methyl-4-iodooctanoic acid Methyl, ethyl 2,2-difluoro-4-methyl-4-iodooctanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−ペンチル基、R6がメチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−メチル−3−ヨードオクタン、1,1,1,2,2−ペンタフルオロ−4−メチル−4−ヨードノナン、1,1,1,2,2,3,3−ヘプタフルオロ−5−メチル−5−ヨードデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−メチル−4−ヨードノナン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−メチル−6−ヨードウンデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−メチル−5−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−メチル−7−ヨードドデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−メチル−6−ヨードウンデカン、1−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−メチル−8−ヨードトリデカン、1−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−メチル−9−ヨードテトラデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−メチル−10−ヨードペンタデカン、2,2−ジフルオロ−3−メチル−3−ヨードオクタン酸メチル、2,2−ジフルオロ−4−メチル−4−ヨードノナン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-pentyl group, and R 6 is a methyl group, include: 1,1-trifluoro-3-methyl-3-iodooctane, 1,1,1,2,2-pentafluoro-4-methyl-4-iodononane, 1,1,1,2,2,3,3 -Heptafluoro-5-methyl-5-iododecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-methyl-4-iodononane, 1,1,1,2,2,3 ,3,4,4-Nonafluoro-6-methyl-6-iodoundecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-methyl-5-iododecane, 1 , 1,1,2,2,3,3,4,4,5,5-undecafluoro-7-methyl-7-iodododecane, 1,1,1,2,2,3,3,4- Octafluoro-4-(trifluoromethyl)-6-methyl-6-iodoundecane, 1-(nonafluorocyclopentyl)-2-methyl-2-iodoheptane, 1,1,1,2,2,3,3 , 4,4,5,5,6,6-tridecafluoro-8-methyl-8-iodotridecane, 1-(undecafluorocyclohexyl)-2-methyl-2-iodoheptane, 1,1,1 , 2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-methyl-9-iodotetradecane, 1,1,1,2,2,3, 3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-methyl-10-iodopentadecane, 2,2-difluoro-3-methyl-3-iodooctanoic acid Methyl, ethyl 2,2-difluoro-4-methyl-4-iodononanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−ヘキシル基、R6がメチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−メチル−3−ヨードノナン、1,1,1,2,2−ペンタフルオロ−4−メチル−4−ヨードデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−メチル−5−ヨードウンデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−メチル−4−ヨードデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−メチル−6−ヨードドデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−メチル−5−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−メチル−7−ヨードトリデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−メチル−6−ヨードドデカン、1−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−メチル−8−ヨードテトラデカン、1−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−メチル−9−ヨードペンタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−メチル−10−ヨードヘキサデカン、2,2−ジフルオロ−4−メチル−4−ヨードデカン酸メチル、2,2−ジフルオロ−4−メチル−4−ヨードデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-hexyl group, and R 6 is a methyl group, include: 1,1-trifluoro-3-methyl-3-iodononane, 1,1,1,2,2-pentafluoro-4-methyl-4-iododecane, 1,1,1,2,2,3,3- Heptafluoro-5-methyl-5-iodoundecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-methyl-4-iododecane, 1,1,1,2,2,3 , 3,4,4-Nonafluoro-6-methyl-6-iodododecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-methyl-5-iodoundecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-methyl-7-iodotridecane, 1,1,1,2,2,3,3,3 4-octafluoro-4-(trifluoromethyl)-6-methyl-6-iodododecane, 1-(nonafluorocyclopentyl)-2-methyl-2-iodooctane, 1,1,1,2,2,3 , 3,4,4,5,5,6,6-tridecafluoro-8-methyl-8-iodotetradecane, 1-(undecafluorocyclohexyl)-2-methyl-2-iodooctane, 1,1, 1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-methyl-9-iodopentadecane, 1,1,1,2,2,3 ,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-methyl-10-iodohexadecane, 2,2-difluoro-4-methyl-4-iododecanoic acid Methyl, ethyl 2,2-difluoro-4-methyl-4-iododecanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−ヘプチル基、R6がメチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−メチル−3−ヨードデカン、1,1,1,2,2−ペンタフルオロ−4−メチル−4−ヨードウンデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−メチル−5−ヨードドデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−メチル−4−ヨードウンデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−メチル−6−ヨードトリデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−メチル−5−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−メチル−7−ヨードテトラデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−メチル−6−ヨードトリデカン、1−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−メチル−8−ヨードペンタデカン、1−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−メチル−9−ヨードヘキサデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−メチル−10−ヨードヘプタデカン、2,2−ジフルオロ−4−メチル−4−ヨードウンデカン酸メチル、2,2−ジフルオロ−4−メチル−4−ヨードウンデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-heptyl group, and R 6 is a methyl group, include: 1,1-trifluoro-3-methyl-3-iododecane, 1,1,1,2,2-pentafluoro-4-methyl-4-iodoundecane, 1,1,1,2,2,3,3 -Heptafluoro-5-methyl-5-iodododecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-methyl-4-iodoundecane, 1,1,1,2,2 ,3,3,4,4-Nonafluoro-6-methyl-6-iodotridecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-methyl-5- Iodododecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-methyl-7-iodotetradecane, 1,1,1,2,2,3 3,4-octafluoro-4-(trifluoromethyl)-6-methyl-6-iodotridecane, 1-(nonafluorocyclopentyl)-2-methyl-2-iodononane, 1,1,1,2,2 , 3,3,4,4,5,5,6,6-tridecafluoro-8-methyl-8-iodopentadecane, 1-(undecafluorocyclohexyl)-2-methyl-2-iodononane, 1,1 , 1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-methyl-9-iodohexadecane, 1,1,1,2,2 3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-methyl-10-iodoheptadecane, 2,2-difluoro-4-methyl-4- Examples thereof include methyl iodoundecanoate and ethyl 2,2-difluoro-4-methyl-4-iodoundecanoate.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−オクチル基、R6がメチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−メチル−3−ヨードウンデカン、1,1,1,2,2−ペンタフルオロ−4−メチル−4−ヨードドデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−メチル−5−ヨードトリデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−メチル−4−ヨードドデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−メチル−6−ヨードテトラデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−メチル−5−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−メチル−7−ヨードペンタデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−メチル−6−ヨードテトラデカン、1−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−メチル−8−ヨードヘキサデカン、1−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−メチル−9−ヨードヘプタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−メチル−10−ヨードオクタデカン、2,2−ジフルオロ−4−メチル−4−ヨードドデカン酸メチル、2,2−ジフルオロ−4−メチル−4−ヨードドデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-octyl group, and R 6 is a methyl group, include: 1,1-trifluoro-3-methyl-3-iodoundecane, 1,1,1,2,2-pentafluoro-4-methyl-4-iodododecane, 1,1,1,2,2,3, 3-heptafluoro-5-methyl-5-iodotridecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-methyl-4-iodododecane, 1,1,1,2 ,2,3,3,4,4-Nonafluoro-6-methyl-6-iodotetradecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-methyl-5 -Iodotridecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-methyl-7-iodopentadecane, 1,1,1,2,2 3,3,4-octafluoro-4-(trifluoromethyl)-6-methyl-6-iodotetradecane, 1-(nonafluorocyclopentyl)-2-methyl-2-iododecane, 1,1,1,2, 2,3,3,4,4,5,5,6,6-tridecafluoro-8-methyl-8-iodohexadecane, 1-(undecafluorocyclohexyl)-2-methyl-2-iododecane, 1, 1,1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-methyl-9-iodoheptadecane, 1,1,1,2, 2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-methyl-10-iodooctadecane, 2,2-difluoro-4-methyl-4 -Methyl iodododecanoate, ethyl 2,2-difluoro-4-methyl-4-iodododecanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−ノニル基、R6がメチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−メチル−3−ヨードドデカン、1,1,1,2,2−ペンタフルオロ−4−メチル−4−ヨードトリデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−メチル−5−ヨードテトラデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−メチル−4−ヨードトリデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−メチル−6−ヨードペンタデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−メチル−5−ヨードテトラデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−メチル−7−ヨードヘキサデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−メチル−6−ヨードペンタデカン、1−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−メチル−8−ヨードヘプタデカン、1−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−メチル−9−ヨードオクタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−メチル−10−ヨードノナデカン、2,2−ジフルオロ−4−メチル−4−ヨードトリデカン酸メチル、2,2−ジフルオロ−4−メチル−4−ヨードトリデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, wherein R 4 is a hydrogen atom, R 5 is an n-nonyl group, and R 6 is a methyl group, include: 1,1-trifluoro-3-methyl-3-iodododecane, 1,1,1,2,2-pentafluoro-4-methyl-4-iodotridecane, 1,1,1,2,2,3 ,3-heptafluoro-5-methyl-5-iodotetradecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-methyl-4-iodotridecane, 1,1,1, 2,2,3,3,4,4-nonafluoro-6-methyl-6-iodopentadecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-methyl- 5-Iodotetradecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-methyl-7-iodohexadecane, 1,1,1,2,2 3,3,4-octafluoro-4-(trifluoromethyl)-6-methyl-6-iodopentadecane, 1-(nonafluorocyclopentyl)-2-methyl-2-iodoundecane, 1,1,1,2 , 2,3,3,4,4,5,5,6,6-tridecafluoro-8-methyl-8-iodoheptadecane, 1-(undecafluorocyclohexyl)-2-methyl-2-iodoundecane , 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-methyl-9-iodooctadecane, 1,1,1, 2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-methyl-10-iodononadecane, 2,2-difluoro-4-methyl- Examples thereof include methyl 4-iodotridecanoate and ethyl 2,2-difluoro-4-methyl-4-iodotridecanoate.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−デシル基、R6がメチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−メチル−3−ヨードトリデカン、1,1,1,2,2−ペンタフルオロ−4−メチル−4−ヨードテトラデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−メチル−5−ヨードペンタデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−メチル−4−ヨードテトラデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−メチル−6−ヨードヘキサデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−メチル−5−ヨードペンタデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−メチル−7−ヨードヘプタデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−メチル−6−ヨードヘキサデカン、1−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−メチル−8−ヨードオクタデカン、1−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−メチル−9−ヨードノナデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−メチル−10−ヨードイコサン、2,2−ジフルオロ−4−メチル−4−ヨードテトラデカン酸メチル、2,2−ジフルオロ−4−メチル−4−ヨードテトラデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-decyl group, and R 6 is a methyl group, include: 1,1-trifluoro-3-methyl-3-iodotridecane, 1,1,1,2,2-pentafluoro-4-methyl-4-iodotetradecane, 1,1,1,2,2,3 ,3-heptafluoro-5-methyl-5-iodopentadecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-methyl-4-iodotetradecane, 1,1,1,2 ,2,3,3,4,4-Nonafluoro-6-methyl-6-iodohexadecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-methyl-5 -Iodopentadecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-methyl-7-iodoheptadecane, 1,1,1,2,2 3,3,4-octafluoro-4-(trifluoromethyl)-6-methyl-6-iodohexadecane, 1-(nonafluorocyclopentyl)-2-methyl-2-iododecane, 1,1,1,2 , 2,3,3,4,4,5,5,6,6-tridecafluoro-8-methyl-8-iodooctadecane, 1-(undecafluorocyclohexyl)-2-methyl-2-iodododecane, 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-methyl-9-iodononadecane, 1,1,1,2, 2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-methyl-10-iodoicosane, 2,2-difluoro-4-methyl-4- Methyl iodotetradecanoate, ethyl 2,2-difluoro-4-methyl-4-iodotetradecanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5及びR6がエチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−エチル−3−ヨードペンタン、1,1,1,2,2−ペンタフルオロ−4−エチル−4−ヨードヘキサン、1,1,1,2,2,3,3−ヘプタフルオロ−5−エチル−5−ヨードヘプタン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−エチル−4−ヨードヘキサン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−エチル−6−ヨードオクタン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−エチル−5−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−エチル−7−ヨードノナン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−エチル−6−ヨードオクタン、1−(ノナフルオロシクロペンチル)−2−エチル−2−ヨードブタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−エチル−8−ヨードデカン、1−(ウンデカフルオロシクロヘキシル)−2−エチル−2−ヨードブタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−エチル−9−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−エチル−10−ヨードドデカン、2,2−ジフルオロ−4−エチル−4−ヨードヘキサン酸メチル、2,2−ジフルオロ−4−エチル−4−ヨードヘキサン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention in which R 4 is a hydrogen atom and R 5 and R 6 are ethyl groups include, for example, 1,1,1-tri Fluoro-3-ethyl-3-iodopentane, 1,1,1,2,2-pentafluoro-4-ethyl-4-iodohexane, 1,1,1,2,2,3,3-heptafluoro- 5-ethyl-5-iodoheptane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-ethyl-4-iodohexane, 1,1,1,2,2,3,3 ,4,4-Nonafluoro-6-ethyl-6-iodooctane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-ethyl-5-iodoheptane, 1, 1,1,2,2,3,3,4,4,5,5-undecafluoro-7-ethyl-7-iodononane, 1,1,1,2,2,3,3,4-octafluoro -4-(trifluoromethyl)-6-ethyl-6-iodooctane, 1-(nonafluorocyclopentyl)-2-ethyl-2-iodobutane, 1,1,1,2,2,3,3,4 4,5,5,6,6-Tridecafluoro-8-ethyl-8-iododecane, 1-(undecafluorocyclohexyl)-2-ethyl-2-iodobutane, 1,1,1,2,2,3 , 3,4,4,5,5,6,6,7,7-pentadecafluoro-9-ethyl-9-iodoundecane, 1,1,1,2,2,3,3,4,4,4 5,5,6,6,7,7,8,8-heptadecafluoro-10-ethyl-10-iodododecane, methyl 2,2-difluoro-4-ethyl-4-iodohexanoate, 2,2- Examples thereof include ethyl difluoro-4-ethyl-4-iodohexanoate.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−プロピル基、R6がエチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−エチル−3−ヨードヘキサン、1,1,1,2,2−ペンタフルオロ−4−エチル−4−ヨードヘプタン、1,1,1,2,2,3,3−ヘプタフルオロ−5−エチル−5−ヨードオクタン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−エチル−4−ヨードヘプタン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−エチル−6−ヨードノナン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−エチル−5−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−エチル−7−ヨードデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−エチル−6−ヨードノナン、1−(ノナフルオロシクロペンチル)−2−エチル−2−ヨードペンタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−エチル−8−ヨードウンデカン、1−(ウンデカフルオロシクロヘキシル)−2−エチル−2−ヨードペンタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−エチル−9−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−エチル−10−ヨードトリデカン、2,2−ジフルオロ−4−エチル−4−ヨードヘプタン酸メチル、2,2−ジフルオロ−4−エチル−4−ヨードヘプタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-propyl group, and R 6 is an ethyl group, include: 1,1-trifluoro-3-ethyl-3-iodohexane, 1,1,1,2,2-pentafluoro-4-ethyl-4-iodoheptane, 1,1,1,2,2,3,3 3-heptafluoro-5-ethyl-5-iodooctane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-ethyl-4-iodoheptane, 1,1,1,2, 2,3,3,4,4-nonafluoro-6-ethyl-6-iodononane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-ethyl-5-iodo Octane, 1,1,1,2,2,3,3,4,5,5-undecafluoro-7-ethyl-7-iododecane, 1,1,1,2,2,3,3,3 4-Octafluoro-4-(trifluoromethyl)-6-ethyl-6-iodononane, 1-(nonafluorocyclopentyl)-2-ethyl-2-iodopentane, 1,1,1,2,2,3,3 3,4,4,5,5,6,6-tridecafluoro-8-ethyl-8-iodoundecane, 1-(undecafluorocyclohexyl)-2-ethyl-2-iodopentane, 1,1,1 , 2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-ethyl-9-iodododecane, 1,1,1,2,2,3, 3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-ethyl-10-iodotridecane, 2,2-difluoro-4-ethyl-4-iodoheptane Methyl acid, ethyl 2,2-difluoro-4-ethyl-4-iodoheptanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−ブチル基、R6がエチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−エチル−3−ヨードヘプタン、1,1,1,2,2−ペンタフルオロ−4−エチル−4−ヨードオクタン、1,1,1,2,2,3,3−ヘプタフルオロ−5−エチル−5−ヨードノナン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−エチル−4−ヨードオクタン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−エチル−6−ヨードデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−エチル−5−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−エチル−7−ヨードウンデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−エチル−6−ヨードデカン、1−(ノナフルオロシクロペンチル)−2−エチル−2−ヨードヘキサン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−エチル−8−ヨードドデカン、1−(ウンデカフルオロシクロヘキシル)−2−エチル−2−ヨードヘキサン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−エチル−9−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−エチル−10−ヨードテトラデカン、2,2−ジフルオロ−4−エチル−4−ヨードオクタン酸メチル、2,2−ジフルオロ−4−エチル−4−ヨードオクタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-butyl group, and R 6 is an ethyl group, include: 1,1-trifluoro-3-ethyl-3-iodoheptane, 1,1,1,2,2-pentafluoro-4-ethyl-4-iodooctane, 1,1,1,2,2,3, 3-heptafluoro-5-ethyl-5-iodononane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-ethyl-4-iodooctane, 1,1,1,2,2 , 3,3,4,4-Nonafluoro-6-ethyl-6-iododecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-ethyl-5-iodononane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-ethyl-7-iodoundecane, 1,1,1,2,2,3,3,4 -Octafluoro-4-(trifluoromethyl)-6-ethyl-6-iododecane, 1-(nonafluorocyclopentyl)-2-ethyl-2-iodohexane, 1,1,1,2,2,3,3 , 4,4,5,5,6,6-tridecafluoro-8-ethyl-8-iodododecane, 1-(undecafluorocyclohexyl)-2-ethyl-2-iodohexane, 1,1,1, 2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-ethyl-9-iodotridecane, 1,1,1,2,2,3,3 3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-ethyl-10-iodotetradecane, 2,2-difluoro-4-ethyl-4-iodooctanoic acid Methyl, ethyl 2,2-difluoro-4-ethyl-4-iodooctanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−ペンチル基、R6がエチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−エチル−3−ヨードオクタン、1,1,1,2,2−ペンタフルオロ−4−エチル−4−ヨードノナン、1,1,1,2,2,3,3−ヘプタフルオロ−5−エチル−5−ヨードデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−エチル−4−ヨードノナン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−エチル−6−ヨードウンデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−エチル−5−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−エチル−7−ヨードドデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−エチル−6−ヨードウンデカン、1−(ノナフルオロシクロペンチル)−2−エチル−2−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−エチル−8−ヨードトリデカン、1−(ウンデカフルオロシクロヘキシル)−2−エチル−2−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−エチル−9−ヨードテトラデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−エチル−10−ヨードペンタデカン、2,2−ジフルオロ−4−エチル−4−ヨードノナン酸メチル、2,2−ジフルオロ−4−エチル−4−ヨードノナン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-pentyl group, and R 6 is an ethyl group, include: 1,1-trifluoro-3-ethyl-3-iodooctane, 1,1,1,2,2-pentafluoro-4-ethyl-4-iodononane, 1,1,1,2,2,3,3 -Heptafluoro-5-ethyl-5-iododecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-ethyl-4-iodononane, 1,1,1,2,2,3 ,3,4,4-Nonafluoro-6-ethyl-6-iodoundecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-ethyl-5-iododecane, 1 , 1,1,2,2,3,3,4,4,5,5-undecafluoro-7-ethyl-7-iodododecane, 1,1,1,2,2,3,3,4- Octafluoro-4-(trifluoromethyl)-6-ethyl-6-iodoundecane, 1-(nonafluorocyclopentyl)-2-ethyl-2-iodoheptane, 1,1,1,2,2,3,3 , 4,4,5,5,6,6-tridecafluoro-8-ethyl-8-iodotridecane, 1-(undecafluorocyclohexyl)-2-ethyl-2-iodoheptane, 1,1,1 , 2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-ethyl-9-iodotetradecane, 1,1,1,2,2,3, 3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-ethyl-10-iodopentadecane, methyl 2,2-difluoro-4-ethyl-4-iodononanoate , 2,2-difluoro-4-ethyl-4-iodononanoate ethyl and the like.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−ヘキシル基、R6がエチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−エチル−3−ヨードノナン、1,1,1,2,2−ペンタフルオロ−4−エチル−4−ヨードデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−エチル−5−ヨードウンデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−エチル−4−ヨードデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−エチル−6−ヨードドデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−エチル−5−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−エチル−7−ヨードトリデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−エチル−6−ヨードドデカン、1−(ノナフルオロシクロペンチル)−2−エチル−2−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−エチル−8−ヨードテトラデカン、1−(ウンデカフルオロシクロヘキシル)−2−エチル−2−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−エチル−9−ヨードペンタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−エチル−10−ヨードヘキサデカン、2,2−ジフルオロ−4−エチル−4−ヨードデカン酸メチル、2,2−ジフルオロ−4−エチル−4−ヨードデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-hexyl group, and R 6 is an ethyl group, include: 1,1-trifluoro-3-ethyl-3-iodononane, 1,1,1,2,2-pentafluoro-4-ethyl-4-iododecane, 1,1,1,2,2,3,3- Heptafluoro-5-ethyl-5-iodoundecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-ethyl-4-iododecane, 1,1,1,2,2,3 ,3,4,4-nonafluoro-6-ethyl-6-iodododecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-ethyl-5-iodoundecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-ethyl-7-iodotridecane, 1,1,1,2,2,3,3,3 4-octafluoro-4-(trifluoromethyl)-6-ethyl-6-iodododecane, 1-(nonafluorocyclopentyl)-2-ethyl-2-iodooctane, 1,1,1,2,2,3 , 3,4,4,5,5,6,6-tridecafluoro-8-ethyl-8-iodotetradecane, 1-(undecafluorocyclohexyl)-2-ethyl-2-iodooctane, 1,1, 1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-ethyl-9-iodopentadecane, 1,1,1,2,2,3 ,3,4,4,5,5,6,6,7,7,8,8-Heptadecafluoro-10-ethyl-10-iodohexadecane, 2,2-difluoro-4-ethyl-4-iododecanoic acid Methyl, ethyl 2,2-difluoro-4-ethyl-4-iododecanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−ヘプチル基、R6がエチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−エチル−3−ヨードデカン、1,1,1,2,2−ペンタフルオロ−4−エチル−4−ヨードウンデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−エチル−5−ヨードドデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−エチル−4−ヨードウンデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−エチル−6−ヨードトリデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−エチル−5−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−エチル−7−ヨードテトラデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−エチル−6−ヨードトリデカン、1−(ノナフルオロシクロペンチル)−2−エチル−2−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−エチル−8−ヨードペンタデカン、1−(ウンデカフルオロシクロヘキシル)−2−エチル−2−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−エチル−9−ヨードヘキサデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−エチル−10−ヨードヘプタデカン、2,2−ジフルオロ−4−エチル−4−ヨードウンデカン酸メチル、2,2−ジフルオロ−4−エチル−4−ヨードウンデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, wherein R 4 is a hydrogen atom, R 5 is an n-heptyl group, and R 6 is an ethyl group, include: 1,1-trifluoro-3-ethyl-3-iododecane, 1,1,1,2,2-pentafluoro-4-ethyl-4-iodoundecane, 1,1,1,2,2,3,3 -Heptafluoro-5-ethyl-5-iodododecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-ethyl-4-iodoundecane, 1,1,1,2,2 ,3,3,4,4-Nonafluoro-6-ethyl-6-iodotridecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-ethyl-5 Iodododecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-ethyl-7-iodotetradecane, 1,1,1,2,2,3,3 3,4-octafluoro-4-(trifluoromethyl)-6-ethyl-6-iodotridecane, 1-(nonafluorocyclopentyl)-2-ethyl-2-iodononane, 1,1,1,2,2 , 3,3,4,4,5,5,6,6-tridecafluoro-8-ethyl-8-iodopentadecane, 1-(undecafluorocyclohexyl)-2-ethyl-2-iodononane, 1,1 , 1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-ethyl-9-iodohexadecane, 1,1,1,2,2 3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-ethyl-10-iodoheptadecane, 2,2-difluoro-4-ethyl-4- Examples thereof include methyl iodoundecanoate and ethyl 2,2-difluoro-4-ethyl-4-iodoundecanoate.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−オクチル基、R6がエチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−エチル−3−ヨードウンデカン、1,1,1,2,2−ペンタフルオロ−4−エチル−4−ヨードドデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−エチル−5−ヨードトリデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−エチル−4−ヨードドデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−エチル−6−ヨードテトラデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−エチル−5−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−エチル−7−ヨードペンタデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−エチル−6−ヨードテトラデカン、1−(ノナフルオロシクロペンチル)−2−エチル−2−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−エチル−8−ヨードヘキサデカン、1−(ウンデカフルオロシクロヘキシル)−2−エチル−2−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−エチル−9−ヨードヘプタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−エチル−10−ヨードオクタデカン、2,2−ジフルオロ−4−エチル−4−ヨードドデカン酸メチル、2,2−ジフルオロ−4−エチル−4−ヨードドデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-octyl group, and R 6 is an ethyl group, include: 1,1-trifluoro-3-ethyl-3-iodoundecane, 1,1,1,2,2-pentafluoro-4-ethyl-4-iodododecane, 1,1,1,2,2,3, 3-heptafluoro-5-ethyl-5-iodotridecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-ethyl-4-iodododecane, 1,1,1,2 ,2,3,3,4,4-Nonafluoro-6-ethyl-6-iodotetradecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-ethyl-5 Iodotridecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-ethyl-7-iodopentadecane, 1,1,1,2,2 3,3,4-octafluoro-4-(trifluoromethyl)-6-ethyl-6-iodotetradecane, 1-(nonafluorocyclopentyl)-2-ethyl-2-iododecane, 1,1,1,2, 2,3,3,4,4,5,5,6,6-tridecafluoro-8-ethyl-8-iodohexadecane, 1-(undecafluorocyclohexyl)-2-ethyl-2-iododecane, 1, 1,1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-ethyl-9-iodoheptadecane, 1,1,1,2, 2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-ethyl-10-iodooctadecane, 2,2-difluoro-4-ethyl-4 -Methyl iodododecanoate, ethyl 2,2-difluoro-4-ethyl-4-iododecanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−ノニル基、R6がエチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−エチル−3−ヨードドデカン、1,1,1,2,2−ペンタフルオロ−4−エチル−4−ヨードトリデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−エチル−5−ヨードテトラデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−エチル−4−ヨードトリデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−エチル−6−ヨードペンタデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−エチル−5−ヨードテトラデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−エチル−7−ヨードヘキサデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−エチル−6−ヨードペンタデカン、1−(ノナフルオロシクロペンチル)−2−エチル−2−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−エチル−8−ヨードヘプタデカン、1−(ウンデカフルオロシクロヘキシル)−2−エチル−2−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−エチル−9−ヨードオクタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−エチル−10−ヨードノナデカン、2,2−ジフルオロ−4−エチル−4−ヨードトリデカン酸メチル、2,2−ジフルオロ−4−エチル−4−ヨードトリデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-nonyl group, and R 6 is an ethyl group, include: 1,1-trifluoro-3-ethyl-3-iodododecane, 1,1,1,2,2-pentafluoro-4-ethyl-4-iodotridecane, 1,1,1,2,2,3 ,3-heptafluoro-5-ethyl-5-iodotetradecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-ethyl-4-iodotridecane, 1,1,1, 2,2,3,3,4,4-nonafluoro-6-ethyl-6-iodopentadecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-ethyl- 5-iodotetradecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-ethyl-7-iodohexadecane, 1,1,1,2,2 3,3,4-octafluoro-4-(trifluoromethyl)-6-ethyl-6-iodopentadecane, 1-(nonafluorocyclopentyl)-2-ethyl-2-iodoundecane, 1,1,1,2 , 2,3,3,4,4,5,5,6,6-tridecafluoro-8-ethyl-8-iodoheptadecane, 1-(undecafluorocyclohexyl)-2-ethyl-2-iodoundecane , 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-ethyl-9-iodooctadecane, 1,1,1, 2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-ethyl-10-iodononadecane, 2,2-difluoro-4-ethyl- Methyl 4-iodotridecanoate, ethyl 2,2-difluoro-4-ethyl-4-iodotridecanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がn−デシル基、R6がエチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−3−エチル−3−ヨードトリデカン、1,1,1,2,2−ペンタフルオロ−4−エチル−4−ヨードテトラデカン、1,1,1,2,2,3,3−ヘプタフルオロ−5−エチル−5−ヨードペンタデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−エチル−4−ヨードテトラデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−6−エチル−6−ヨードヘキサデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−エチル−5−ヨードペンタデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−エチル−7−ヨードヘプタデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−エチル−6−ヨードヘキサデカン、1−(ノナフルオロシクロペンチル)−2−エチル−2−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−エチル−8−ヨードオクタデカン、1−(ウンデカフルオロシクロヘキシル)−2−エチル−2−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−エチル−9−ヨードノナデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−エチル−10−ヨードイコサン、2,2−ジフルオロ−4−エチル−4−ヨードテトラデカン酸メチル、2,2−ジフルオロ−4−エチル−4−ヨードテトラデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is an n-decyl group, and R 6 is an ethyl group, include: 1,1-trifluoro-3-ethyl-3-iodotridecane, 1,1,1,2,2-pentafluoro-4-ethyl-4-iodotetradecane, 1,1,1,2,2,3 ,3-heptafluoro-5-ethyl-5-iodopentadecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-ethyl-4-iodotetradecane, 1,1,1,2 ,2,3,3,4,4-Nonafluoro-6-ethyl-6-iodohexadecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-5-ethyl-5 -Iodopentadecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-ethyl-7-iodoheptadecane, 1,1,1,2,2 3,3,4-Octafluoro-4-(trifluoromethyl)-6-ethyl-6-iodohexadecane, 1-(nonafluorocyclopentyl)-2-ethyl-2-iododecane, 1,1,1,2 , 2,3,3,4,4,5,5,6,6-tridecafluoro-8-ethyl-8-iodooctadecane, 1-(undecafluorocyclohexyl)-2-ethyl-2-iododecane, 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-ethyl-9-iodononadecane, 1,1,1,2, 2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-ethyl-10-iodoicosane, 2,2-difluoro-4-ethyl-4- Examples include methyl iodotetradecanoate, ethyl 2,2-difluoro-4-ethyl-4-iodotetradecanoate, and the like.
本発明の一般式(5)で表される含フッ素化合物で、R4及びR6がメチル基、R5が水素原子である化合物としては、具体的には例えば、1,1,1−トリフルオロ−2−メチル−3−ヨードブタン、1,1,1,2,2−ペンタフルオロ−3−メチル−4−ヨードペンタン、1,1,1,2,2,3,3−ヘプタフルオロ−4−メチル−5−ヨードヘキサン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−メチル−4−ヨードペンタン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−メチル−6−ヨードヘプタン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−メチル−5−ヨードヘキサン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−メチル−7−ヨードオクタン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−メチル−6−ヨードヘプタン、2−(ノナフルオロシクロペンチル)−3−ヨードブタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−メチル−8−ヨードノナン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードブタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−メチル−9−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−メチル−10−ヨードウンデカン、2,2−ジフルオロ−3−メチル−4−ヨードペンタン酸メチル、2,2−ジフルオロ−3−メチル−4−ヨードペンタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention in which R 4 and R 6 are methyl groups and R 5 is a hydrogen atom include, for example, 1,1,1-tri Fluoro-2-methyl-3-iodobutane, 1,1,1,2,2-pentafluoro-3-methyl-4-iodopentane, 1,1,1,2,2,3,3-heptafluoro-4 -Methyl-5-iodohexane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-methyl-4-iodopentane, 1,1,1,2,2,3,3, 4,4-Nonafluoro-5-methyl-6-iodoheptane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-methyl-5-iodohexane, 1,1 ,1,2,2,3,3,4,4,5,5-undecafluoro-6-methyl-7-iodooctane, 1,1,1,2,2,3,3,4-octafluoro -4-(trifluoromethyl)-5-methyl-6-iodoheptane, 2-(nonafluorocyclopentyl)-3-iodobutane, 1,1,1,2,2,3,3,4,4,5 5,6,6-Tridecafluoro-7-methyl-8-iodononane, 2-(undecafluorocyclohexyl)-3-iodobutane, 1,1,1,2,2,3,3,4,4,5 , 5,6,6,7,7-Pentadecafluoro-8-methyl-9-iododecane, 1,1,1,2,2,3,3,4,4,5,5,6,6,7 ,7,8,8-Heptadecafluoro-9-methyl-10-iodoundecane, methyl 2,2-difluoro-3-methyl-4-iodopentanoate, 2,2-difluoro-3-methyl-4-iodo Examples include ethyl pentanoate and the like.
本発明の一般式(5)で表される含フッ素化合物で、R4がメチル基、R5が水素原子、R6がエチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−2−メチル−3−ヨードペンタン、1,1,1,2,2−ペンタフルオロ−3−メチル−4−ヨードヘキサン、1,1,1,2,2,3,3−ヘプタフルオロ−4−メチル−5−ヨードヘプタン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−メチル−4−ヨードヘキサン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−メチル−6−ヨードオクタン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−メチル−5−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−メチル−7−ヨードノナン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−メチル−6−ヨードオクタン、2−(ノナフルオロシクロペンチル)−3−ヨードペンタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−メチル−8−ヨードデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードペンタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−メチル−9−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−メチル−10−ヨードドデカン、2,2−ジフルオロ−3−メチル−4−ヨードヘキサン酸メチル、2,2−ジフルオロ−3−メチル−4−ヨードヘキサン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, wherein R 4 is a methyl group, R 5 is a hydrogen atom, and R 6 is an ethyl group, include: 1-trifluoro-2-methyl-3-iodopentane, 1,1,1,2,2-pentafluoro-3-methyl-4-iodohexane, 1,1,1,2,2,3,3- Heptafluoro-4-methyl-5-iodoheptane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-methyl-4-iodohexane, 1,1,1,2,2 3,3,4,4-Nonafluoro-5-methyl-6-iodooctane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-methyl-5-iodoheptane , 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-6-methyl-7-iodononane, 1,1,1,2,2,3,3,4 -Octafluoro-4-(trifluoromethyl)-5-methyl-6-iodooctane, 2-(nonafluorocyclopentyl)-3-iodopentane, 1,1,1,2,2,3,3,4. 4,5,5,6,6-Tridecafluoro-7-methyl-8-iododecane, 2-(undecafluorocyclohexyl)-3-iodopentane, 1,1,1,2,2,3,3,3 4,4,5,5,6,6,7,7-pentadecafluoro-8-methyl-9-iodoundecane, 1,1,1,2,2,3,3,4,4,5,5 , 6,6,7,7,8,8-Heptadecafluoro-9-methyl-10-iododecane, methyl 2,2-difluoro-3-methyl-4-iodohexanoate, 2,2-difluoro-3 -Methyl-4-iodohexanoic acid ethyl etc. are mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4がメチル基、R5が水素原子、R6がn−プロピル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−2−メチル−3−ヨードヘキサン、1,1,1,2,2−ペンタフルオロ−3−メチル−4−ヨードヘプタン、1,1,1,2,2,3,3−ヘプタフルオロ−4−メチル−5−ヨードオクタン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−メチル−4−ヨードヘプタン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−メチル−6−ヨードノナン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−メチル−5−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−メチル−7−ヨードデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−メチル−6−ヨードノナン、2−(ノナフルオロシクロペンチル)−3−ヨードヘキサン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−メチル−8−ヨードウンデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードヘキサン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−メチル−9−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−メチル−10−ヨードトリデカン、2,2−ジフルオロ−3−メチル−4−ヨードヘプタン酸メチル、2,2−ジフルオロ−3−メチル−4−ヨードヘプタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a methyl group, R 5 is a hydrogen atom, and R 6 is an n-propyl group, include: 1,1-trifluoro-2-methyl-3-iodohexane, 1,1,1,2,2-pentafluoro-3-methyl-4-iodoheptane, 1,1,1,2,2,3, 3-heptafluoro-4-methyl-5-iodooctane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-methyl-4-iodoheptane, 1,1,1,2, 2,3,3,4,4-nonafluoro-5-methyl-6-iodononane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-methyl-5-iodo Octane, 1,1,1,2,2,3,3,4,5,5-undecafluoro-6-methyl-7-iododecane, 1,1,1,2,2,3,3,3 4-octafluoro-4-(trifluoromethyl)-5-methyl-6-iodononane, 2-(nonafluorocyclopentyl)-3-iodohexane, 1,1,1,2,2,3,3,4, 4,5,5,6,6-tridecafluoro-7-methyl-8-iodoundecane, 2-(undecafluorocyclohexyl)-3-iodohexane, 1,1,1,2,2,3,3 , 4,4,5,5,6,6,7,7-pentadecafluoro-8-methyl-9-iodododecane, 1,1,1,2,2,3,3,4,4,5 5,6,6,7,7,8,8-Heptadecafluoro-9-methyl-10-iodotridecane, methyl 2,2-difluoro-3-methyl-4-iodoheptanoate, 2,2-difluoro Examples thereof include ethyl-3-methyl-4-iodoheptanoate.
本発明の一般式(5)で表される含フッ素化合物で、R4がメチル基、R5が水素原子、R6がn−ブチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−2−メチル−3−ヨードヘプタン、1,1,1,2,2−ペンタフルオロ−3−メチル−4−ヨードオクタン、1,1,1,2,2,3,3−ヘプタフルオロ−4−メチル−5−ヨードノナン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−メチル−4−ヨードオクタン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−メチル−6−ヨードデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−メチル−5−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−メチル−7−ヨードウンデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−メチル−6−ヨードデカン、2−(ノナフルオロシクロペンチル)−3−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−メチル−8−ヨードドデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−メチル−9−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−メチル−10−ヨードテトラデカン、2,2−ジフルオロ−3−メチル−4−ヨードオクタン酸メチル、2,2−ジフルオロ−3−メチル−4−ヨードオクタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a methyl group, R 5 is a hydrogen atom, and R 6 is an n-butyl group, include: 1,1-trifluoro-2-methyl-3-iodoheptane, 1,1,1,2,2-pentafluoro-3-methyl-4-iodooctane, 1,1,1,2,2,3, 3-heptafluoro-4-methyl-5-iodononane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-methyl-4-iodooctane, 1,1,1,2,2 , 3,3,4,4-Nonafluoro-5-methyl-6-iododecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-methyl-5-iodononane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-6-methyl-7-iodoundecane, 1,1,1,2,2,3,3,4 -Octafluoro-4-(trifluoromethyl)-5-methyl-6-iododecane, 2-(nonafluorocyclopentyl)-3-iodoheptane, 1,1,1,2,2,3,3,4,4 , 5,5,6,6-Tridecafluoro-7-methyl-8-iodododecane, 2-(undecafluorocyclohexyl)-3-iodoheptane, 1,1,1,2,2,3,3,3 4,4,5,5,6,6,7,7-pentadecafluoro-8-methyl-9-iodotridecane, 1,1,1,2,2,3,3,4,4,5 5,6,6,7,7,8,8-Heptadecafluoro-9-methyl-10-iodotetradecane, methyl 2,2-difluoro-3-methyl-4-iodooctanoate, 2,2-difluoro- Ethyl 3-methyl-4-iodooctanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4がメチル基、R5が水素原子、R6がn−ペンチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−2−メチル−3−ヨードオクタン、1,1,1,2,2−ペンタフルオロ−3−メチル−4−ヨードノナン、1,1,1,2,2,3,3−ヘプタフルオロ−4−メチル−5−ヨードデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−メチル−4−ヨードノナン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−メチル−6−ヨードウンデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−メチル−5−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−メチル−7−ヨードドデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−メチル−6−ヨードウンデカン、2−(ノナフルオロシクロペンチル)−3−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−メチル−8−ヨードトリデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−メチル−9−ヨードテトラデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−メチル−10−ヨードペンタデカン、2,2−ジフルオロ−3−メチル−4−ヨードノナン酸メチル、2,2−ジフルオロ−3−メチル−4−ヨードノナン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a methyl group, R 5 is a hydrogen atom, and R 6 is an n-pentyl group, include: 1,1-trifluoro-2-methyl-3-iodooctane, 1,1,1,2,2-pentafluoro-3-methyl-4-iodononane, 1,1,1,2,2,3,3 -Heptafluoro-4-methyl-5-iododecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-methyl-4-iodononane, 1,1,1,2,2,3 ,3,4,4-Nonafluoro-5-methyl-6-iodoundecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-methyl-5-iododecane, 1 , 1,1,2,2,3,3,4,4,5,5-undecafluoro-6-methyl-7-iodododecane, 1,1,1,2,2,3,3,4- Octafluoro-4-(trifluoromethyl)-5-methyl-6-iodoundecane, 2-(nonafluorocyclopentyl)-3-iodooctane, 1,1,1,2,2,3,3,4,4 , 5,5,6,6-Tridecafluoro-7-methyl-8-iodotridecane, 2-(undecafluorocyclohexyl)-3-iodooctane, 1,1,1,2,2,3,3 , 4,4,5,5,6,6,7,7-pentadecafluoro-8-methyl-9-iodotetradecane, 1,1,1,2,2,3,3,4,4,5 5,6,6,7,7,8,8-Heptadecafluoro-9-methyl-10-iodopentadecane, methyl 2,2-difluoro-3-methyl-4-iodononanoate, 2,2-difluoro-3 -Methyl-4-iodononanoic acid ethyl etc. are mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4がメチル基、R5が水素原子、R6がn−ヘキシル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−2−メチル−3−ヨードノナン、1,1,1,2,2−ペンタフルオロ−3−メチル−4−ヨードデカン、1,1,1,2,2,3,3−ヘプタフルオロ−4−メチル−5−ヨードウンデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−メチル−4−ヨードデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−メチル−6−ヨードドデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−メチル−5−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−メチル−7−ヨードトリデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−メチル−6−ヨードドデカン、2−(ノナフルオロシクロペンチル)−3−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−メチル−8−ヨードテトラデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−メチル−9−ヨードペンタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−メチル−10−ヨードヘキサデカン、2,2−ジフルオロ−3−メチル−4−ヨードデカン酸メチル、2,2−ジフルオロ−3−メチル−4−ヨードデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a methyl group, R 5 is a hydrogen atom, and R 6 is an n-hexyl group, include: 1,1-trifluoro-2-methyl-3-iodononane, 1,1,1,2,2-pentafluoro-3-methyl-4-iododecane, 1,1,1,2,2,3,3- Heptafluoro-4-methyl-5-iodoundecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-methyl-4-iododecane, 1,1,1,2,2,3 , 3,4,4-Nonafluoro-5-methyl-6-iodododecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-methyl-5-iodoundecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-6-methyl-7-iodotridecane, 1,1,1,2,2,3,3,3 4-Octafluoro-4-(trifluoromethyl)-5-methyl-6-iodododecane, 2-(nonafluorocyclopentyl)-3-iodononane, 1,1,1,2,2,3,3,4. 4,5,5,6,6-tridecafluoro-7-methyl-8-iodotetradecane, 2-(undecafluorocyclohexyl)-3-iodononane, 1,1,1,2,2,3,3,3 4,4,5,5,6,6,7,7-pentadecafluoro-8-methyl-9-iodopentadecane, 1,1,1,2,2,3,3,4,4,5,5 , 6,6,7,7,8,8-Heptadecafluoro-9-methyl-10-iodohexadecane, methyl 2,2-difluoro-3-methyl-4-iododecanoate, 2,2-difluoro-3- Examples include methyl-4-iododecanoate ethyl and the like.
本発明の一般式(5)で表される含フッ素化合物で、R4がメチル基、R5が水素原子、R6がn−ヘプチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−2−メチル−3−ヨードデカン、1,1,1,2,2−ペンタフルオロ−3−メチル−4−ヨードウンデカン、1,1,1,2,2,3,3−ヘプタフルオロ−4−メチル−5−ヨードドデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−メチル−4−ヨードウンデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−メチル−6−ヨードトリデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−メチル−5−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−メチル−7−ヨードテトラデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−メチル−6−ヨードトリデカン、2−(ノナフルオロシクロペンチル)−3−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−メチル−8−ヨードペンタデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−メチル−9−ヨードヘキサデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−メチル−10−ヨードヘプタデカン、2,2−ジフルオロ−3−メチル−4−ヨードウンデカン酸メチル、2,2−ジフルオロ−3−メチル−4−ヨードウンデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a methyl group, R 5 is a hydrogen atom, and R 6 is an n-heptyl group, include: 1,1-trifluoro-2-methyl-3-iododecane, 1,1,1,2,2-pentafluoro-3-methyl-4-iodoundecane, 1,1,1,2,2,3,3 -Heptafluoro-4-methyl-5-iodododecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-methyl-4-iodoundecane, 1,1,1,2,2 ,3,3,4,4-Nonafluoro-5-methyl-6-iodotridecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-methyl-5- Iodododecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-6-methyl-7-iodotetradecane, 1,1,1,2,2,3, 3,4-octafluoro-4-(trifluoromethyl)-5-methyl-6-iodotridecane, 2-(nonafluorocyclopentyl)-3-iododecane, 1,1,1,2,2,3,3 , 4,4,5,5,6,6-Tridecafluoro-7-methyl-8-iodopentadecane, 2-(undecafluorocyclohexyl)-3-iododecane, 1,1,1,2,2,3 , 3,4,4,5,5,6,6,7,7-pentadecafluoro-8-methyl-9-iodohexadecane, 1,1,1,2,2,3,3,4,4,4 5,5,6,6,7,7,8,8-heptadecafluoro-9-methyl-10-iodoheptadecane, methyl 2,2-difluoro-3-methyl-4-iodoundecanoate, 2,2 -Ethyl difluoro-3-methyl-4-iodoundecanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4がメチル基、R5が水素原子、R6がn−オクチル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−2−メチル−3−ヨードウンデカン、1,1,1,2,2−ペンタフルオロ−3−メチル−4−ヨードドデカン、1,1,1,2,2,3,3−ヘプタフルオロ−4−メチル−5−ヨードトリデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−メチル−4−ヨードドデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−メチル−6−ヨードテトラデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−メチル−5−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−メチル−7−ヨードペンタデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−メチル−6−ヨードテトラデカン、2−(ノナフルオロシクロペンチル)−3−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−メチル−8−ヨードヘキサデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−メチル−9−ヨードヘプタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−メチル−10−ヨードオクタデカン、2,2−ジフルオロ−3−メチル−4−ヨードドデカン酸メチル、2,2−ジフルオロ−3−メチル−4−ヨードドデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a methyl group, R 5 is a hydrogen atom, and R 6 is an n-octyl group, include: 1,1-trifluoro-2-methyl-3-iodoundecane, 1,1,1,2,2-pentafluoro-3-methyl-4-iodododecane, 1,1,1,2,2,3, 3-heptafluoro-4-methyl-5-iodotridecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-methyl-4-iodododecane, 1,1,1,2 ,2,3,3,4,4-Nonafluoro-5-methyl-6-iodotetradecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-methyl-5 Iodotridecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-6-methyl-7-iodopentadecane, 1,1,1,2,2 3,3,4-octafluoro-4-(trifluoromethyl)-5-methyl-6-iodotetradecane, 2-(nonafluorocyclopentyl)-3-iodoundecane, 1,1,1,2,2,3 , 3,4,4,5,5,6,6-tridecafluoro-7-methyl-8-iodohexadecane, 2-(undecafluorocyclohexyl)-3-iodoundecane, 1,1,1,2, 2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-8-methyl-9-iodoheptadecane, 1,1,1,2,2,3,3,3 4,4,5,5,6,6,7,7,8,8-heptadecafluoro-9-methyl-10-iodooctadecane, methyl 2,2-difluoro-3-methyl-4-iodododecanoate, Ethyl 2,2-difluoro-3-methyl-4-iodododecanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4がメチル基、R5が水素原子、R6がn−ノニル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−2−メチル−3−ヨードドデカン、1,1,1,2,2−ペンタフルオロ−3−メチル−4−ヨードトリデカン、1,1,1,2,2,3,3−ヘプタフルオロ−4−メチル−5−ヨードテトラデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−メチル−4−ヨードトリデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−メチル−6−ヨードペンタデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−メチル−5−ヨードテトラデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−メチル−7−ヨードヘキサデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−メチル−6−ヨードペンタデカン、2−(ノナフルオロシクロペンチル)−3−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−メチル−8−ヨードヘプタデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−メチル−9−ヨードオクタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−メチル−10−ヨードノナデカン、2,2−ジフルオロ−3−メチル−4−ヨードトリデカン酸メチル、2,2−ジフルオロ−3−メチル−4−ヨードトリデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a methyl group, R 5 is a hydrogen atom, and R 6 is an n-nonyl group, include: 1,1-trifluoro-2-methyl-3-iodododecane, 1,1,1,2,2-pentafluoro-3-methyl-4-iodotridecane, 1,1,1,2,2,3 ,3-heptafluoro-4-methyl-5-iodotetradecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-methyl-4-iodotridecane, 1,1,1, 2,2,3,3,4,4-nonafluoro-5-methyl-6-iodopentadecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-methyl- 5-Iodotetradecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-6-methyl-7-iodohexadecane, 1,1,1,2,2 3,3,4-octafluoro-4-(trifluoromethyl)-5-methyl-6-iodopentadecane, 2-(nonafluorocyclopentyl)-3-iodododecane, 1,1,1,2,2,3 , 3,4,4,5,5,6,6-Tridecafluoro-7-methyl-8-iodoheptadecane, 2-(undecafluorocyclohexyl)-3-iodododecane, 1,1,1,2 , 2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-8-methyl-9-iodooctadecane, 1,1,1,2,2,3,3,3 4,4,5,5,6,6,7,7,8,8-heptadecafluoro-9-methyl-10-iodononadecane, methyl 2,2-difluoro-3-methyl-4-iodotridecanoate, Ethyl 2,2-difluoro-3-methyl-4-iodotridecanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4がメチル基、R5が水素原子、R6がn−デシル基である化合物としては、具体的には例えば、1,1,1−トリフルオロ−2−メチル−3−ヨードトリデカン、1,1,1,2,2−ペンタフルオロ−3−メチル−4−ヨードテトラデカン、1,1,1,2,2,3,3−ヘプタフルオロ−4−メチル−5−ヨードペンタデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−メチル−4−ヨードテトラデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−メチル−6−ヨードヘキサデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−メチル−5−ヨードペンタデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−メチル−7−ヨードヘプタデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−メチル−6−ヨードヘキサデカン、2−(ノナフルオロシクロペンチル)−3−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−メチル−8−ヨードオクタデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−メチル−9−ヨードノナデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−メチル−10−ヨードイコサン、2,2−ジフルオロ−3−メチル−4−ヨードテトラデカン酸メチル、2,2−ジフルオロ−3−メチル−4−ヨードテトラデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a methyl group, R 5 is a hydrogen atom, and R 6 is an n-decyl group, include: 1,1-trifluoro-2-methyl-3-iodotridecane, 1,1,1,2,2-pentafluoro-3-methyl-4-iodotetradecane, 1,1,1,2,2,3 ,3-heptafluoro-4-methyl-5-iodopentadecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-methyl-4-iodotetradecane, 1,1,1,2 ,2,3,3,4,4-Nonafluoro-5-methyl-6-iodohexadecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-methyl-5 -Iodopentadecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-6-methyl-7-iodoheptadecane, 1,1,1,2,2 3,3,4-octafluoro-4-(trifluoromethyl)-5-methyl-6-iodohexadecane, 2-(nonafluorocyclopentyl)-3-iodotridecane, 1,1,1,2,2 3,3,4,4,5,5,6,6-tridecafluoro-7-methyl-8-iodooctadecane, 2-(undecafluorocyclohexyl)-3-iodotridecane, 1,1,1, 2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-8-methyl-9-iodononadecane, 1,1,1,2,2,3,3,3 4,4,5,5,6,6,7,7,8,8-heptadecafluoro-9-methyl-10-iodoicosane, methyl 2,2-difluoro-3-methyl-4-iodotetradecanoate, 2 , Ethyl 2-difluoro-3-methyl-4-iodotetradecanoate and the like.
本発明の一般式(5)で表される含フッ素化合物で、R4がエチル基、R5が水素原子、R6がエチル基である化合物としては、具体的には例えば、3−(トリフルオロメチル)−4−ヨードヘキサン、1,1,1,2,2−ペンタフルオロ−3−エチル−4−ヨードヘキサン、1,1,1,2,2,3,3−ヘプタフルオロ−4−エチル−5−ヨードヘプタン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−エチル−4−ヨードヘキサン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−エチル−6−ヨードオクタン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−エチル−5−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−エチル−7−ヨードノナン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−エチル−6−ヨードオクタン、2−(ノナフルオロシクロペンチル)−3−ヨードヘキサン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−エチル−8−ヨードデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードヘキサン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−エチル−9−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−エチル−10−ヨードドデカン、2,2−ジフルオロ−3−エチル−4−ヨードヘキサン酸メチル、2,2−ジフルオロ−3−エチル−4−ヨードヘキサン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is an ethyl group, R 5 is a hydrogen atom, and R 6 is an ethyl group, include 3-(tri Fluoromethyl)-4-iodohexane, 1,1,1,2,2-pentafluoro-3-ethyl-4-iodohexane, 1,1,1,2,2,3,3-heptafluoro-4- Ethyl-5-iodoheptane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-ethyl-4-iodohexane, 1,1,1,2,2,3,3,4 ,4-Nonafluoro-5-ethyl-6-iodooctane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-ethyl-5-iodoheptane, 1,1, 1,2,2,3,3,4,4,5,5-undecafluoro-6-ethyl-7-iodononane, 1,1,1,2,2,3,3,4-octafluoro-4 -(Trifluoromethyl)-5-ethyl-6-iodooctane, 2-(nonafluorocyclopentyl)-3-iodohexane, 1,1,1,2,2,3,3,4,5,5 ,6,6-Tridecafluoro-7-ethyl-8-iododecane, 2-(undecafluorocyclohexyl)-3-iodohexane, 1,1,1,2,2,3,3,4,4,5 , 5,6,6,7,7-Pentadecafluoro-8-ethyl-9-iodoundecane, 1,1,1,2,2,3,3,4,4,5,5,6,6,6 7,7,8,8-Heptadecafluoro-9-ethyl-10-iodododecane, methyl 2,2-difluoro-3-ethyl-4-iodohexanoate, 2,2-difluoro-3-ethyl-4- Examples thereof include ethyl iodohexanoate.
本発明の一般式(5)で表される含フッ素化合物で、R4がエチル基、R5が水素原子、R6がn−プロピル基である化合物としては、具体的には例えば、3−(トリフルオロメチル)−4−ヨードヘプタン、1,1,1,2,2−ペンタフルオロ−3−エチル−4−ヨードヘプタン、1,1,1,2,2,3,3−ヘプタフルオロ−4−エチル−5−ヨードオクタン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−エチル−4−ヨードヘプタン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−エチル−6−ヨードノナン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−エチル−5−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−エチル−7−ヨードデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−エチル−6−ヨードノナン、2−(ノナフルオロシクロペンチル)−3−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−エチル−8−ヨードウンデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードヘプタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−エチル−9−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−エチル−10−ヨードトリデカン、2,2−ジフルオロ−3−エチル−4−ヨードヘプタン酸メチル、2,2−ジフルオロ−3−エチル−4−ヨードヘプタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is an ethyl group, R 5 is a hydrogen atom, and R 6 is an n-propyl group, include 3- (Trifluoromethyl)-4-iodoheptane, 1,1,1,2,2-pentafluoro-3-ethyl-4-iodoheptane, 1,1,1,2,2,3,3-heptafluoro- 4-ethyl-5-iodooctane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-ethyl-4-iodoheptane, 1,1,1,2,2,3,3 ,4,4-Nonafluoro-5-ethyl-6-iodononane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-ethyl-5-iodooctane, 1,1 , 1,2,2,3,3,4,4,5,5-undecafluoro-6-ethyl-7-iododecane, 1,1,1,2,2,3,3,4-octafluoro- 4-(trifluoromethyl)-5-ethyl-6-iodononane, 2-(nonafluorocyclopentyl)-3-iodoheptane, 1,1,1,2,2,3,3,4,4,5,5 ,6,6-Tridecafluoro-7-ethyl-8-iodoundecane, 2-(undecafluorocyclohexyl)-3-iodoheptane, 1,1,1,2,2,3,3,4,4,4. 5,5,6,6,7,7-pentadecafluoro-8-ethyl-9-iodododecane, 1,1,1,2,2,3,3,4,5,5,6,6 , 7,7,8,8-Heptadecafluoro-9-ethyl-10-iodotridecane, methyl 2,2-difluoro-3-ethyl-4-iodoheptanoate, 2,2-difluoro-3-ethyl- 4-Iodoheptanoic acid ethyl etc. are mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4がエチル基、R5が水素原子、R6がn−ブチル基である化合物としては、具体的には例えば、3−(トリフルオロメチル)−4−ヨードオクタン、1,1,1,2,2−ペンタフルオロ−3−エチル−4−ヨードオクタン、1,1,1,2,2,3,3−ヘプタフルオロ−4−エチル−5−ヨードノナン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−エチル−4−ヨードオクタン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−エチル−6−ヨードデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−エチル−5−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−エチル−7−ヨードウンデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−エチル−6−ヨードデカン、2−(ノナフルオロシクロペンチル)−3−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−エチル−8−ヨードドデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードオクタン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−エチル−9−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−エチル−10−ヨードテトラデカン、2,2−ジフルオロ−3−エチル−4−ヨードオクタン酸メチル、2,2−ジフルオロ−3−エチル−4−ヨードオクタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is an ethyl group, R 5 is a hydrogen atom, and R 6 is an n-butyl group, include 3- (Trifluoromethyl)-4-iodooctane, 1,1,1,2,2-pentafluoro-3-ethyl-4-iodooctane, 1,1,1,2,2,3,3-heptafluoro- 4-ethyl-5-iodononane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-ethyl-4-iodooctane, 1,1,1,2,2,3,3,3 4,4-Nonafluoro-5-ethyl-6-iododecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-ethyl-5-iodononane, 1,1,1 , 2,2,3,3,4,4,5,5-undecafluoro-6-ethyl-7-iodoundecane, 1,1,1,2,2,3,3,4-octafluoro-4 -(Trifluoromethyl)-5-ethyl-6-iododecane, 2-(nonafluorocyclopentyl)-3-iodooctane, 1,1,1,2,2,3,3,4,5,5,5 6,6-Tridecafluoro-7-ethyl-8-iodododecane, 2-(undecafluorocyclohexyl)-3-iodooctane, 1,1,1,2,2,3,3,4,4,5 , 5,6,6,7,7-Pentadecafluoro-8-ethyl-9-iodotridecane, 1,1,1,2,2,3,3,4,4,5,5,6,6 , 7,7,8,8-Heptadecafluoro-9-ethyl-10-iodotetradecane, methyl 2,2-difluoro-3-ethyl-4-iodooctanoate, 2,2-difluoro-3-ethyl-4 -Ethyl iodooctanoate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4がエチル基、R5が水素原子、R6がn−ペンチル基である化合物としては、具体的には例えば、3−(トリフルオロメチル)−4−ヨードノナン、1,1,1,2,2−ペンタフルオロ−3−エチル−4−ヨードノナン、1,1,1,2,2,3,3−ヘプタフルオロ−4−エチル−5−ヨードデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−エチル−4−ヨードノナン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−エチル−6−ヨードウンデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−エチル−5−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−エチル−7−ヨードドデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−エチル−6−ヨードウンデカン、2−(ノナフルオロシクロペンチル)−3−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−エチル−8−ヨードトリデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードノナン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−エチル−9−ヨードテトラデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−エチル−10−ヨードペンタデカン、2,2−ジフルオロ−3−エチル−4−ヨードノナン酸メチル、2,2−ジフルオロ−3−エチル−4−ヨードノナン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is an ethyl group, R 5 is a hydrogen atom, and R 6 is an n-pentyl group, include 3- (Trifluoromethyl)-4-iodononane, 1,1,1,2,2-pentafluoro-3-ethyl-4-iodononane, 1,1,1,2,2,3,3-heptafluoro-4- Ethyl-5-iododecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-ethyl-4-iodononane, 1,1,1,2,2,3,3,4,4 -Nonafluoro-5-ethyl-6-iodoundecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-ethyl-5-iododecane, 1,1,1,2 , 2,3,3,4,4,5,5-undecafluoro-6-ethyl-7-iodododecane, 1,1,1,2,2,3,3,4-octafluoro-4-( Trifluoromethyl)-5-ethyl-6-iodoundecane, 2-(nonafluorocyclopentyl)-3-iodononane, 1,1,1,2,2,3,3,4,5,5,6,6. 6-tridecafluoro-7-ethyl-8-iodotridecane, 2-(undecafluorocyclohexyl)-3-iodononane, 1,1,1,2,2,3,3,4,4,5,5 , 6,6,7,7-Pentadecafluoro-8-ethyl-9-iodotetradecane, 1,1,1,2,2,3,3,4,4,5,5,6,6,7, 7,8,8-Heptadecafluoro-9-ethyl-10-iodopentadecane, methyl 2,2-difluoro-3-ethyl-4-iodononanoate, ethyl 2,2-difluoro-3-ethyl-4-iodononanoate Etc.
本発明の一般式(5)で表される含フッ素化合物で、R4がエチル基、R5が水素原子、R6がn−ヘキシル基である化合物としては、具体的には例えば、3−(トリフルオロメチル)−4−ヨードデカン、1,1,1,2,2−ペンタフルオロ−3−エチル−4−ヨードデカン、1,1,1,2,2,3,3−ヘプタフルオロ−4−エチル−5−ヨードウンデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−エチル−4−ヨードデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−エチル−6−ヨードドデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−エチル−5−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−エチル−7−ヨードトリデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−エチル−6−ヨードドデカン、2−(ノナフルオロシクロペンチル)−3−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−エチル−8−ヨードテトラデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−エチル−9−ヨードペンタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−エチル−10−ヨードヘキサデカン、2,2−ジフルオロ−3−エチル−4−ヨードデカン酸メチル、2,2−ジフルオロ−3−エチル−4−ヨードデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is an ethyl group, R 5 is a hydrogen atom, and R 6 is an n-hexyl group, include 3- (Trifluoromethyl)-4-iododecane, 1,1,1,2,2-pentafluoro-3-ethyl-4-iododecane, 1,1,1,2,2,3,3-heptafluoro-4- Ethyl-5-iodoundecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-ethyl-4-iododecane, 1,1,1,2,2,3,3,4. 4-Nonafluoro-5-ethyl-6-iodododecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-ethyl-5-iodoundecane, 1,1,1 , 2,2,3,3,4,4,5,5-undecafluoro-6-ethyl-7-iodotridecane, 1,1,1,2,2,3,3,4-octafluoro- 4-(trifluoromethyl)-5-ethyl-6-iodododecane, 2-(nonafluorocyclopentyl)-3-iododecane, 1,1,1,2,2,3,3,4,4,5,5 ,6,6-Tridecafluoro-7-ethyl-8-iodotetradecane, 2-(undecafluorocyclohexyl)-3-iododecane, 1,1,1,2,2,3,3,4,4,5 , 5,6,6,7,7-pentadecafluoro-8-ethyl-9-iodopentadecane, 1,1,1,2,2,3,3,4,5,5,6,6,6 7,7,8,8-Heptadecafluoro-9-ethyl-10-iodohexadecane, methyl 2,2-difluoro-3-ethyl-4-iododecanoate, 2,2-difluoro-3-ethyl-4-iododecane Ethyl acid and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4がエチル基、R5が水素原子、R6がn−ヘプチル基である化合物としては、具体的には例えば、3−(トリフルオロメチル)−4−ヨードウンデカン、1,1,1,2,2−ペンタフルオロ−3−エチル−4−ヨードウンデカン、1,1,1,2,2,3,3−ヘプタフルオロ−4−エチル−5−ヨードドデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−エチル−4−ヨードウンデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−エチル−6−ヨードトリデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−エチル−5−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−エチル−7−ヨードテトラデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−エチル−6−ヨードトリデカン、2−(ノナフルオロシクロペンチル)−3−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−エチル−8−ヨードペンタデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードウンデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−エチル−9−ヨードヘキサデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−エチル−10−ヨードヘプタデカン、2,2−ジフルオロ−3−エチル−4−ヨードウンデカン酸メチル、2,2−ジフルオロ−3−エチル−4−ヨードウンデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, wherein R 4 is an ethyl group, R 5 is a hydrogen atom, and R 6 is an n-heptyl group, include, for example, 3- (Trifluoromethyl)-4-iodoundecane, 1,1,1,2,2-pentafluoro-3-ethyl-4-iodoundecane, 1,1,1,2,2,3,3-heptafluoro- 4-ethyl-5-iodododecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-ethyl-4-iodoundecane, 1,1,1,2,2,3,3 ,4,4-Nonafluoro-5-ethyl-6-iodotridecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-ethyl-5-iodododecane, 1 , 1,1,2,2,3,3,4,4,5,5-undecafluoro-6-ethyl-7-iodotetradecane, 1,1,1,2,2,3,3,4- Octafluoro-4-(trifluoromethyl)-5-ethyl-6-iodotridecane, 2-(nonafluorocyclopentyl)-3-iodoundecane, 1,1,1,2,2,3,3,4. 4,5,5,6,6-Tridecafluoro-7-ethyl-8-iodopentadecane, 2-(undecafluorocyclohexyl)-3-iodoundecane, 1,1,1,2,2,3,3 , 4,4,5,5,6,6,7,7-pentadecafluoro-8-ethyl-9-iodohexadecane, 1,1,1,2,2,3,3,4,4,5 5,6,6,7,7,8,8-Heptadecafluoro-9-ethyl-10-iodoheptadecane, methyl 2,2-difluoro-3-ethyl-4-iodoundecanoate, 2,2-difluoro Examples include ethyl-3-ethyl-4-iodoundecanoate and the like.
本発明の一般式(5)で表される含フッ素化合物で、R4がエチル基、R5が水素原子、R6がn−オクチル基である化合物としては、具体的には例えば、3−(トリフルオロメチル)−4−ヨードドデカン、1,1,1,2,2−ペンタフルオロ−3−エチル−4−ヨードドデカン、1,1,1,2,2,3,3−ヘプタフルオロ−4−エチル−5−ヨードトリデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−エチル−4−ヨードドデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−エチル−6−ヨードテトラデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−エチル−5−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−エチル−7−ヨードペンタデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−エチル−6−ヨードテトラデカン、2−(ノナフルオロシクロペンチル)−3−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−エチル−8−ヨードヘキサデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードドデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−エチル−9−ヨードヘプタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−エチル−10−ヨードオクタデカン、2,2−ジフルオロ−3−エチル−4−ヨードドデカン酸メチル、2,2−ジフルオロ−3−エチル−4−ヨードドデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is an ethyl group, R 5 is a hydrogen atom, and R 6 is an n-octyl group, include, for example, 3- (Trifluoromethyl)-4-iodododecane, 1,1,1,2,2-pentafluoro-3-ethyl-4-iodododecane, 1,1,1,2,2,3,3-heptafluoro- 4-ethyl-5-iodotridecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-ethyl-4-iodododecane, 1,1,1,2,2,3, 3,4,4-nonafluoro-5-ethyl-6-iodotetradecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-ethyl-5-iodotridecane, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-6-ethyl-7-iodopentadecane, 1,1,1,2,2,3,3,4 -Octafluoro-4-(trifluoromethyl)-5-ethyl-6-iodotetradecane, 2-(nonafluorocyclopentyl)-3-iodododecane, 1,1,1,2,2,3,3,4. 4,5,5,6,6-Tridecafluoro-7-ethyl-8-iodohexadecane, 2-(undecafluorocyclohexyl)-3-iodododecane, 1,1,1,2,2,3,3 , 4,4,5,5,6,6,7,7-pentadecafluoro-8-ethyl-9-iodoheptadecane, 1,1,1,2,2,3,3,4,4,5 , 5,6,6,7,7,8,8-Heptadecafluoro-9-ethyl-10-iodooctadecane, methyl 2,2-difluoro-3-ethyl-4-iodododecanoate, 2,2-difluoro Examples thereof include ethyl-3-ethyl-4-iodododecanoate.
本発明の一般式(5)で表される含フッ素化合物で、R4がエチル基、R5が水素原子、R6がn−ノニル基である化合物としては、具体的には例えば、3−(トリフルオロメチル)−4−ヨードトリデカン、1,1,1,2,2−ペンタフルオロ−3−エチル−4−ヨードトリデカン、1,1,1,2,2,3,3−ヘプタフルオロ−4−エチル−5−ヨードテトラデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−エチル−4−ヨードトリデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−エチル−6−ヨードペンタデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−エチル−5−ヨードテトラデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−エチル−7−ヨードヘキサデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−エチル−6−ヨードペンタデカン、2−(ノナフルオロシクロペンチル)−3−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−エチル−8−ヨードヘプタデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードトリデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−エチル−9−ヨードオクタデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−エチル−10−ヨードノナデカン、2,2−ジフルオロ−3−エチル−4−ヨードトリデカン酸メチル、2,2−ジフルオロ−3−エチル−4−ヨードトリデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is an ethyl group, R 5 is a hydrogen atom, and R 6 is an n-nonyl group, include 3- (Trifluoromethyl)-4-iodotridecane, 1,1,1,2,2-pentafluoro-3-ethyl-4-iodotridecane, 1,1,1,2,2,3,3-hepta Fluoro-4-ethyl-5-iodotetradecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-ethyl-4-iodotridecane, 1,1,1,2,2 3,3,4,4-Nonafluoro-5-ethyl-6-iodopentadecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-ethyl-5-iodotetradecane , 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-6-ethyl-7-iodohexadecane, 1,1,1,2,2,3,3,3 4-octafluoro-4-(trifluoromethyl)-5-ethyl-6-iodopentadecane, 2-(nonafluorocyclopentyl)-3-iodotridecane, 1,1,1,2,2,3,3,3 4,4,5,5,6,6-tridecafluoro-7-ethyl-8-iodoheptadecane, 2-(undecafluorocyclohexyl)-3-iodotridecane, 1,1,1,2,2 , 3,3,4,4,5,5,6,6,7,7-pentadecafluoro-8-ethyl-9-iodooctadecane, 1,1,1,2,2,3,3,4, 4,5,5,6,6,7,7,8,8-heptadecafluoro-9-ethyl-10-iodononadecane, methyl 2,2-difluoro-3-ethyl-4-iodotridecanoate, 2, Examples thereof include ethyl 2-difluoro-3-ethyl-4-iodotridecanoate.
本発明の一般式(5)で表される含フッ素化合物で、R4がエチル基、R5が水素原子、R6がn−デシル基である化合物としては、具体的には例えば、3−(トリフルオロメチル)−4−ヨードテトラデカン、1,1,1,2,2−ペンタフルオロ−3−エチル−4−ヨードテトラデカン、1,1,1,2,2,3,3−ヘプタフルオロ−4−エチル−5−ヨードペンタデカン、1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−3−エチル−4−ヨードテトラデカン、1,1,1,2,2,3,3,4,4−ノナフルオロ−5−エチル−6−ヨードヘキサデカン、1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−4−エチル−5−ヨードペンタデカン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−6−エチル−7−ヨードヘプタデカン、1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−5−エチル−6−ヨードヘキサデカン、2−(ノナフルオロシクロペンチル)−3−ヨードテトラデカン、1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−エチル−8−ヨードオクタデカン、2−(ウンデカフルオロシクロヘキシル)−3−ヨードテトラデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−8−エチル−9−ヨードノナデカン、1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−9−エチル−10−ヨードイコサン、2,2−ジフルオロ−3−エチル−4−ヨードテトラデカン酸メチル、2,2−ジフルオロ−3−エチル−4−ヨードテトラデカン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is an ethyl group, R 5 is a hydrogen atom, and R 6 is an n-decyl group, include 3- (Trifluoromethyl)-4-iodotetradecane, 1,1,1,2,2-pentafluoro-3-ethyl-4-iodotetradecane, 1,1,1,2,2,3,3-heptafluoro- 4-ethyl-5-iodopentadecane, 1,1,1,2-tetrafluoro-2-(trifluoromethyl)-3-ethyl-4-iodotetradecane, 1,1,1,2,2,3,3 ,4,4-Nonafluoro-5-ethyl-6-iodohexadecane, 1,1,1,2,2,3-hexafluoro-3-(trifluoromethyl)-4-ethyl-5-iodopentadecane, 1, 1,1,2,2,3,3,4,4,5,5-undecafluoro-6-ethyl-7-iodoheptadecane, 1,1,1,2,2,3,3,4- Octafluoro-4-(trifluoromethyl)-5-ethyl-6-iodohexadecane, 2-(nonafluorocyclopentyl)-3-iodotetradecane, 1,1,1,2,2,3,3,4,4 ,5,5,6,6-Tridecafluoro-7-ethyl-8-iodooctadecane, 2-(undecafluorocyclohexyl)-3-iodotetradecane, 1,1,1,2,2,3,3,3 4,4,5,5,6,6,7,7-pentadecafluoro-8-ethyl-9-iodononadecane, 1,1,1,2,2,3,3,4,4,5,5,5 6,6,7,7,8,8-Heptadecafluoro-9-ethyl-10-iodoicosane, methyl 2,2-difluoro-3-ethyl-4-iodotetradecanoate, 2,2-difluoro-3-ethyl Examples include ethyl-4-iodotetradecanoate and the like.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5及びR6がフェニル基である化合物としては、具体的には例えば、3,3,3−トリフルオロ−1,1−ジフェニル−1−ヨードプロパン、3,3,4,4,4−ペンタフルオロ−1,1−ジフェニル−1−ヨードブタン、3,3,4,4,5,5,5−ヘプタフルオロ−1,1−ジフェニル−1−ヨードペンタン、3,4,4,4−テトラフルオロ−3−(トリフルオロメチル)−1,1−ジフェニル−1−ヨードブタン、3,3,4,4,5,5,6,6,6−ノナフルオロ−1,1−ジフェニル−1−ヨードヘキサン、3,4,4,5,5,5−ヘキサフルオロ−1,1−ジフェニル−1−ヨードペンタン、3,3,4,4,5,5,6,6,7,7,7−ウンデカフルオロ−1,1−ジフェニル−1−ヨードヘプタン、3,4,4,5,5,6,6,6−オクタフルオロ−3−(トリフルオロメチル)−1,1−ジフェニル−1−ヨードヘキサン、2−(ノナフルオロシクロペンチル)−1,1−ジフェニル−1−ヨードエタン、3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−1,1−ジフェニル−1−ヨードオクタン、2−(ウンデカフルオロシクロヘキシル)−1,1−ジフェニル−1−ヨードエタン、3,3,4,4,5,5,6,6,7,7,8,8,9,9,9−ペンタデカフルオロ−1,1−ジフェニル−1−ヨードノナン、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ヘプタデカフルオロ−1,1−ジフェニル−1−ヨードデカン、2,2−ジフルオロ−4,4−ジフェニル−4−ヨードブタン酸メチル、2,2−ジフルオロ−4,4−ジフェニル−4−ヨードブタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom and R 5 and R 6 are phenyl groups, include, for example, 3,3,3-tri Fluoro-1,1-diphenyl-1-iodopropane, 3,3,4,4,4-pentafluoro-1,1-diphenyl-1-iodobutane, 3,3,4,4,5,5,5- Heptafluoro-1,1-diphenyl-1-iodopentane, 3,4,4,4-tetrafluoro-3-(trifluoromethyl)-1,1-diphenyl-1-iodobutane, 3,3,4,4 , 5,5,6,6,6-nonafluoro-1,1-diphenyl-1-iodohexane, 3,4,4,5,5,5-hexafluoro-1,1-diphenyl-1-iodopentane, 3,3,4,4,5,5,6,6,7,7,7-undecafluoro-1,1-diphenyl-1-iodoheptane, 3,4,4,5,5,6,6 ,6-Octafluoro-3-(trifluoromethyl)-1,1-diphenyl-1-iodohexane, 2-(nonafluorocyclopentyl)-1,1-diphenyl-1-iodoethane, 3,3,4,4 , 5,5,6,6,7,7,8,8,8-tridecafluoro-1,1-diphenyl-1-iodooctane, 2-(undecafluorocyclohexyl)-1,1-diphenyl-1 -Iodoethane, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-pentadecafluoro-1,1-diphenyl-1-iodononane, 3,3 , 4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1,1-diphenyl-1-iododecane, 2,2-difluoro Examples include methyl -4,4-diphenyl-4-iodobutanoate and ethyl 2,2-difluoro-4,4-diphenyl-4-iodobutanoate.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がメチル基、R6がメトキシカルボニル基である化合物としては、具体的には例えば、4,4,4−トリフルオロ−2−メチル−2−ヨードブタン酸メチル、4,4,5,5,5−ペンタフルオロ−2−メチル−2−ヨードペンタン酸メチル、4,4,5,5,6,6,6−ヘプタフルオロ−2−メチル−2−ヨードヘキサン酸メチル、4,5,5,5−テトラフルオロ−4−(トリフルオロメチル)−2−メチル−2−ヨードペンタン酸メチル、4,4,5,5,6,6,7,7,7−ノナフルオロ−2−メチル−2−ヨードヘプタン酸メチル、4,5,5,6,6,6−ヘキサフルオロ−4−(トリフルオロメチル)−2−メチル−2−ヨードヘキサン酸メチル、4,4,5,5,6,6,7,7,8,8,8−ウンデカフルオロ−2−メチル−2−ヨードオクタン酸メチル、4,5,5,6,6,7,7,7−オクタフルオロ−3−(トリフルオロメチル)−2−メチル−2−ヨードヘプタン酸メチル、3−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードプロピオン酸メチル、4,4,5,5,6,6,7,7,8,8,9,9,9−トリデカフルオロ−2−メチル−2−ヨードノナン酸メチル、3−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードプロピオン酸メチル、4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ペンタデカフルオロ−2−メチル−2−ヨードデカン酸メチル、4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11−ヘプタデカフルオロ−2−メチル−2−ヨードウンデカン酸メチル、2,2−ジフルオロ−4−(メトキシカルボニル)−4−ヨードペンタン酸メチル、2,2−ジフルオロ−4−(メトキシカルボニル)−4−ヨードペンタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is a methyl group, and R 6 is a methoxycarbonyl group, include: , Methyl 4-trifluoro-2-methyl-2-iodobutanoate, 4,4,5,5,5-Methyl pentafluoro-2-methyl-2-iodopentanoate 4,4,5,5,6 Methyl 6,6-heptafluoro-2-methyl-2-iodohexanoate, 4,5,5,5-tetrafluoro-4-(trifluoromethyl)-2-methyl-2-iodopentanoate, 4, Methyl 4,5,5,6,6,7,7,7-nonafluoro-2-methyl-2-iodoheptanoate, 4,5,5,6,6,6-hexafluoro-4-(trifluoromethyl ) Methyl 2-methyl-2-iodohexanoate, 4,4,5,5,6,6,7,7,8,8,8-methyl undecafluoro-2-methyl-2-iodooctanoate, Methyl 4,5,5,6,6,7,7,7-octafluoro-3-(trifluoromethyl)-2-methyl-2-iodoheptanoate, 3-(nonafluorocyclopentyl)-2-methyl- Methyl 2-iodopropionate, 4,4,5,5,6,6,7,7,8,8,9,9,9-methyl tridecafluoro-2-methyl-2-iodononanoate, 3-( Undecafluorocyclohexyl)-2-methyl-2-iodopropionate methyl, 4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro Methyl-2-methyl-2-iododecanoate, 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2 -Methyl-2-iodoundecanoate, methyl 2,2-difluoro-4-(methoxycarbonyl)-4-iodopentanoate, ethyl 2,2-difluoro-4-(methoxycarbonyl)-4-iodopentanoate, etc. Is mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がメチル基、R6がエトキシカルボニル基である化合物としては、具体的には例えば、4,4,4−トリフルオロ−2−メチル−2−ヨードブタン酸エチル、4,4,5,5,5−ペンタフルオロ−2−メチル−2−ヨードペンタン酸エチル、4,4,5,5,6,6,6−ヘプタフルオロ−2−メチル−2−ヨードヘキサン酸エチル、4,5,5,5−テトラフルオロ−4−(トリフルオロメチル)−2−メチル−2−ヨードペンタン酸エチル、4,4,5,5,6,6,7,7,7−ノナフルオロ−2−メチル−2−ヨードヘプタン酸エチル、4,5,5,6,6,6−ヘキサフルオロ−4−(トリフルオロメチル)−2−メチル−2−ヨードヘキサン酸エチル、4,4,5,5,6,6,7,7,8,8,8−ウンデカフルオロ−2−メチル−2−ヨードオクタン酸エチル、4,5,5,6,6,7,7,7−オクタフルオロ−3−(トリフルオロメチル)−2−メチル−2−ヨードヘプタン酸エチル、3−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードプロピオン酸エチル、4,4,5,5,6,6,7,7,8,8,9,9,9−トリデカフルオロ−2−メチル−2−ヨードノナン酸エチル、3−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードプロピオン酸エチル、4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ペンタデカフルオロ−2−メチル−2−ヨードデカン酸エチル、4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11−ヘプタデカフルオロ−2−メチル−2−ヨードウンデカン酸エチル、2,2−ジフルオロ−4−(エトキシカルボニル)−4−ヨードペンタン酸メチル、2,2−ジフルオロ−4−(エトキシカルボニル)−4−ヨードペンタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is a methyl group, and R 6 is an ethoxycarbonyl group, include: , Ethyl 4-trifluoro-2-methyl-2-iodobutanoate, 4,4,5,5,5-Ethyl pentafluoro-2-methyl-2-iodopentanoate, 4,4,5,5,6 Ethyl 6,6-heptafluoro-2-methyl-2-iodohexanoate, 4,5,5,5-tetrafluoro-4-(trifluoromethyl)-2-methyl-2-iodopentanoate, 4, Ethyl 4,5,5,6,6,7,7,7-nonafluoro-2-methyl-2-iodoheptanoate, 4,5,5,6,6,6-hexafluoro-4-(trifluoromethyl ) Ethyl 2-methyl-2-iodohexanoate, 4,4,5,5,6,6,7,7,8,8,8-ethyl undecafluoro-2-methyl-2-iodooctanoate, Ethyl 4,5,5,6,6,7,7,7-octafluoro-3-(trifluoromethyl)-2-methyl-2-iodoheptanoate, 3-(nonafluorocyclopentyl)-2-methyl- Ethyl 2-iodopropionate, 4,4,5,5,6,6,7,7,8,8,9,9,9-ethyl tridecafluoro-2-methyl-2-iodononanoate, 3-( Undecafluorocyclohexyl)-2-methyl-2-iodopropionate ethyl, 4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro Ethyl-2-methyl-2-iododecanoate, 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2 -Ethyl methyl-2-iodoundecanoate, methyl 2,2-difluoro-4-(ethoxycarbonyl)-4-iodopentanoate, ethyl 2,2-difluoro-4-(ethoxycarbonyl)-4-iodopentanoate, etc. Is mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がメチル基、R6が2−イソプロピルアダマンタン−2−イルオキシカルボニル基である化合物としては、具体的には例えば、4,4,4−トリフルオロ−2−メチル−2−ヨードブタン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,5−ペンタフルオロ−2−メチル−2−ヨードペンタン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,6,6,6−ヘプタフルオロ−2−メチル−2−ヨードヘキサン酸(2−イソプロピルアダマンタン−2−イル)、4,5,5,5−テトラフルオロ−4−(トリフルオロメチル)−2−メチル−2−ヨードペンタン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,6,6,7,7,7−ノナフルオロ−2−メチル−2−ヨードヘプタン酸(2−イソプロピルアダマンタン−2−イル)、4,5,5,6,6,6−ヘキサフルオロ−4−(トリフルオロメチル)−2−メチル−2−ヨードヘキサン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,6,6,7,7,8,8,8−ウンデカフルオロ−2−メチル−2−ヨードオクタン酸(2−イソプロピルアダマンタン−2−イル)、4,5,5,6,6,7,7,7−オクタフルオロ−3−(トリフルオロメチル)−2−メチル−2−ヨードヘプタン酸(2−イソプロピルアダマンタン−2−イル)、3−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードプロピオン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,6,6,7,7,8,8,9,9,9−トリデカフルオロ−2−メチル−2−ヨードノナン酸(2−イソプロピルアダマンタン−2−イル)、3−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードプロピオン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ペンタデカフルオロ−2−メチル−2−ヨードデカン酸(2−イソプロピルアダマンタン−2−イル)、4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11−ヘプタデカフルオロ−2−メチル−2−ヨードウンデカン酸(2−イソプロピルアダマンタン−2−イル)、2,2−ジフルオロ−4−[(2−イソプロピルアダマンタン−2−イル)オキシカルボニル]−4−ヨードペンタン酸メチル、2,2−ジフルオロ−4−[(2−イソプロピルアダマンタン−2−イル)オキシカルボニル]−4−ヨードペンタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is a methyl group, and R 6 is a 2-isopropyladamantan-2-yloxycarbonyl group Specifically, for example, 4,4,4-trifluoro-2-methyl-2-iodobutanoic acid (2-isopropyladamantan-2-yl), 4,4,5,5,5-pentafluoro-2-methyl- 2-iodopentanoic acid (2-isopropyladamantan-2-yl), 4,4,5,5,6,6,6-heptafluoro-2-methyl-2-iodohexanoic acid (2-isopropyladamantan-2-yl) Yl), 4,5,5,5-tetrafluoro-4-(trifluoromethyl)-2-methyl-2-iodopentanoic acid (2-isopropyladamantan-2-yl), 4,4,5,5,5 6,6,7,7,7-Nonafluoro-2-methyl-2-iodoheptanoic acid (2-isopropyladamantan-2-yl), 4,5,5,6,6,6-hexafluoro-4-( Trifluoromethyl)-2-methyl-2-iodohexanoic acid (2-isopropyladamantan-2-yl), 4,4,5,5,6,6,7,7,8,8,8-undecafluoro 2-Methyl-2-iodooctanoic acid (2-isopropyladamantan-2-yl), 4,5,5,6,6,7,7,7-octafluoro-3-(trifluoromethyl)-2- Methyl-2-iodoheptanoic acid (2-isopropyladamantan-2-yl), 3-(nonafluorocyclopentyl)-2-methyl-2-iodopropionic acid (2-isopropyladamantan-2-yl), 4,4. 5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-methyl-2-iodononanoic acid (2-isopropyladamantan-2-yl), 3-(undeca Fluorocyclohexyl)-2-methyl-2-iodopropionic acid (2-isopropyladamantan-2-yl), 4,4,5,5,6,6,7,7,8,8,9,9,10, 10,10-Pentadecafluoro-2-methyl-2-iododecanoic acid (2-isopropyladamantan-2-yl), 4,4,5,5,6,6,7,7,8,8,9,9 , 10,10,11,11,11-Heptadecafluoro-2-methyl-2-iodoundecanoic acid (2-isopropyladamantan-2-yl), 2,2-difluoro-4-[(2-isopropyladamantane- 2-yl) Oki Examples include methyl cycarbonyl]-4-iodopentanoate, ethyl 2,2-difluoro-4-[(2-isopropyladamantan-2-yl)oxycarbonyl]-4-iodopentanoate, and the like.
本発明の一般式(5)で表される含フッ素化合物で、R4が水素原子、R5がメチル基、R6がイソボルネン−2−イルオキシカルボニル基である化合物としては、具体的には例えば、4,4,4−トリフルオロ−2−メチル−2−ヨードブタン酸(イソボルネン−2−イル)、4,4,5,5,5−ペンタフルオロ−2−メチル−2−ヨードペンタン酸(イソボルネン−2−イル)、4,4,5,5,6,6,6−ヘプタフルオロ−2−メチル−2−ヨードヘキサン酸(イソボルネン−2−イル)、4,5,5,5−テトラフルオロ−4−(トリフルオロメチル)−2−メチル−2−ヨードペンタン酸(イソボルネン−2−イル)、4,4,5,5,6,6,7,7,7−ノナフルオロ−2−メチル−2−ヨードヘプタン酸(イソボルネン−2−イル)、4,5,5,6,6,6−ヘキサフルオロ−4−(トリフルオロメチル)−2−メチル−2−ヨードヘキサン酸(イソボルネン−2−イル)、4,4,5,5,6,6,7,7,8,8,8−ウンデカフルオロ−2−メチル−2−ヨードオクタン酸(イソボルネン−2−イル)、4,5,5,6,6,7,7,7−オクタフルオロ−3−(トリフルオロメチル)−2−メチル−2−ヨードヘプタン酸(イソボルネン−2−イル)、3−(ノナフルオロシクロペンチル)−2−メチル−2−ヨードプロピオン酸(イソボルネン−2−イル)、4,4,5,5,6,6,7,7,8,8,9,9,9−トリデカフルオロ−2−メチル−2−ヨードノナン酸(イソボルネン−2−イル)、3−(ウンデカフルオロシクロヘキシル)−2−メチル−2−ヨードプロピオン酸(イソボルネン−2−イル)、4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ペンタデカフルオロ−2−メチル−2−ヨードデカン酸(イソボルネン−2−イル)、4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11−ヘプタデカフルオロ−2−メチル−2−ヨードウンデカン酸(イソボルネン−2−イル)、2,2−ジフルオロ−4−[(イソボルネン−2−イル)オキシカルボニル]−4−ヨードペンタン酸メチル、2,2−ジフルオロ−4−[(イソボルネン−2−イル)オキシカルボニル]−4−ヨードペンタン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 is a hydrogen atom, R 5 is a methyl group, and R 6 is an isobornen-2-yloxycarbonyl group, For example, 4,4,4-trifluoro-2-methyl-2-iodobutanoic acid (isobornen-2-yl), 4,4,5,5,5-pentafluoro-2-methyl-2-iodopentanoic acid ( Isobornen-2-yl), 4,4,5,5,6,6,6-heptafluoro-2-methyl-2-iodohexanoic acid (isobornen-2-yl), 4,5,5,5-tetra Fluoro-4-(trifluoromethyl)-2-methyl-2-iodopentanoic acid (isobornen-2-yl), 4,4,5,5,6,6,7,7,7-nonafluoro-2-methyl -2-iodoheptanoic acid (isobornen-2-yl), 4,5,5,6,6,6-hexafluoro-4-(trifluoromethyl)-2-methyl-2-iodohexanoic acid (isobornene-2) -Yl), 4,4,5,5,6,6,7,7,8,8,8-undecafluoro-2-methyl-2-iodooctanoic acid (isobornen-2-yl), 4,5 , 5,6,6,7,7,7-Octafluoro-3-(trifluoromethyl)-2-methyl-2-iodoheptanoic acid (isobornen-2-yl), 3-(nonafluorocyclopentyl)-2 -Methyl-2-iodopropionic acid (isobornen-2-yl), 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-methyl- 2-Iodononanoic acid (isobornen-2-yl), 3-(undecafluorocyclohexyl)-2-methyl-2-iodopropionic acid (isobornen-2-yl), 4,4,5,5,6,6,6 7,7,8,8,9,9,10,10,10-pentadecafluoro-2-methyl-2-iododecanoic acid (isobornen-2-yl), 4,4,5,5,6,6,6 7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-methyl-2-iodoundecanoic acid (isobornen-2-yl), 2,2-difluoro-4 Examples include methyl -[(isobornen-2-yl)oxycarbonyl]-4-iodopentanoate and ethyl 2,2-difluoro-4-[(isobornen-2-yl)oxycarbonyl]-4-iodopentanoate. ..
本発明の一般式(5)で表される含フッ素化合物で、R4とR5が縮環して5員環を形成している化合物としては、具体的には例えば、1−ヨード−2−(トリフルオロメチル)シクロペンタン、1−ヨード−2−(ペンタフルオロエチル)シクロペンタン、1−ヨード−2−(ヘプタフルオロ−n−プロピル)シクロペンタン、1−ヨード−2−(ヘプタフルオロ−iso−プロピル)シクロペンタン、1−ヨード−2−(ノナフルオロ−n−ブチル)シクロペンタン、1−ヨード−2−(ノノフルオロ−sec−ブチル)シクロペンタン、1−ヨード−2−(ウンデカフルオロ−n−ペンチル)シクロペンタン、1−ヨード−2−(ウンデカフルオロ−sec−ペンチル)シクロペンタン、1−ヨード−2−(トリデカフルオロシクロペンチル)シクロペンタン、1−ヨード−2−(トリデカフルオロ−n−ヘキシル)シクロペンタン、1−ヨード−2−(ウンデカフルオロシクロヘキシル)シクロペンタン、1−ヨード−2−(ペンタデカフルオロ−n−ヘプチル)シクロペンタン、1−ヨード−2−(ヘプタデカフルオロ−n−オクチル)シクロペンタン、(2−ヨードシクロペンチル)ジフルオロ酢酸メチル、(2−ヨードシクロペンチル)ジフルオロ酢酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 and R 5 are condensed to form a 5-membered ring, include 1-iodo-2. -(Trifluoromethyl)cyclopentane, 1-iodo-2-(pentafluoroethyl)cyclopentane, 1-iodo-2-(heptafluoro-n-propyl)cyclopentane, 1-iodo-2-(heptafluoro- iso-propyl)cyclopentane, 1-iodo-2-(nonafluoro-n-butyl)cyclopentane, 1-iodo-2-(nonofluoro-sec-butyl)cyclopentane, 1-iodo-2-(undecafluoro- n-pentyl)cyclopentane, 1-iodo-2-(undecafluoro-sec-pentyl)cyclopentane, 1-iodo-2-(tridecafluorocyclopentyl)cyclopentane, 1-iodo-2-(tridecafluoro) -N-hexyl)cyclopentane, 1-iodo-2-(undecafluorocyclohexyl)cyclopentane, 1-iodo-2-(pentadecafluoro-n-heptyl)cyclopentane, 1-iodo-2-(heptadeca) Examples thereof include fluoro-n-octyl)cyclopentane, methyl (2-iodocyclopentyl)difluoroacetate, and ethyl (2-iodocyclopentyl)difluoroacetate.
本発明の一般式(5)で表される含フッ素化合物で、R4とR5が縮環して6員環を形成している化合物としては、具体的には例えば、1−ヨード−2−(トリフルオロメチル)シクロヘキサン、1−ヨード−2−(ペンタフルオロエチル)シクロヘキサン、1−ヨード−2−(ヘプタフルオロ−n−プロピル)シクロヘキサン、1−ヨード−2−(ヘプタフルオロ−iso−プロピル)シクロヘキサン、1−ヨード−2−(ノナフルオロ−n−ブチル)シクロヘキサン、1−ヨード−2−(ノナフルオロ−sec−ブチル)シクロヘキサン、1−ヨード−2−(ウンデカフルオロ−n−ペンチル)シクロヘキサン、1−ヨード−2−(ウンデカフルオロ−sec−ペンチル)シクロヘキサン、1−ヨード−2−(ノナフルオロシクロペンチル)シクロヘキサン、1−ヨード−2−(トリデカフルオロ−n−ヘキシル)シクロヘキサン、1−ヨード−2−(ウンデカフルオロシクロヘキシル)シクロヘキサン、1−ヨード−2−(ペンタデカフルオロ−n−ヘプチル)シクロヘキサン、1−ヨード−2−(ヘプタデカフルオロ−n−オクチル)シクロヘキサン、(2−ヨードシクロヘキシル)ジフルオロ酢酸メチル、(2−ヨードシクロヘキシル)ジフルオロ酢酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 and R 5 are condensed to form a 6-membered ring, include 1-iodo-2. -(Trifluoromethyl)cyclohexane, 1-iodo-2-(pentafluoroethyl)cyclohexane, 1-iodo-2-(heptafluoro-n-propyl)cyclohexane, 1-iodo-2-(heptafluoro-iso-propyl) ) Cyclohexane, 1-iodo-2-(nonafluoro-n-butyl)cyclohexane, 1-iodo-2-(nonafluoro-sec-butyl)cyclohexane, 1-iodo-2-(undecafluoro-n-pentyl)cyclohexane, 1-iodo-2-(undecafluoro-sec-pentyl)cyclohexane, 1-iodo-2-(nonafluorocyclopentyl)cyclohexane, 1-iodo-2-(tridecafluoro-n-hexyl)cyclohexane, 1-iodo -2-(Undecafluorocyclohexyl)cyclohexane, 1-iodo-2-(pentadecafluoro-n-heptyl)cyclohexane, 1-iodo-2-(heptadecafluoro-n-octyl)cyclohexane, (2-iodocyclohexyl) ) Methyl difluoroacetate, ethyl (2-iodocyclohexyl)difluoroacetate and the like can be mentioned.
本発明の一般式(5)で表される含フッ素化合物で、R4とR5が縮環して7員環を形成している化合物としては、具体的には例えば、1−ヨード−2−(トリフルオロメチル)シクロヘプタン、1−ヨード−2−(ペンタフルオロエチル)シクロヘプタン、1−ヨード−2−(ヘプタフルオロ−n−プロピル)シクロヘプタン、1−ヨード−2−(ヘプタフルオロ−iso−プロピル)シクロヘプタン、1−ヨード−2−(ノナフルオロ−n−ブチル)シクロヘプタン、1−ヨード−2−(ノナフルオロ−sec−ブチル)シクロヘプタン、1−ヨード−2−(ウンデカフルオロ−n−ペンチル)シクロヘプタン、1−ヨード−2−(ウンデカフルオロ−sec−ペンチル)シクロヘプタン、1−ヨード−2−(ノナフルオロシクロペンチル)シクロヘプタン、1−ヨード−2−(トリデカフルオロ−n−ヘキシル)シクロヘプタン、1−ヨード−2−(ウンデカフルオロシクロヘキシル)シクロヘプタン、1−ヨード−2−(ペンタデカフルオロ−n−ヘプチル)シクロヘプタン、1−ヨード−2−(ヘプタデカフルオロ−n−オクチル)シクロヘプタン、(2−ヨードシクロヘプチル)ジフルオロ酢酸メチル、(2−ヨードシクロヘプチル)ジフルオロ酢酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 and R 5 are condensed to form a 7-membered ring, include 1-iodo-2. -(Trifluoromethyl)cycloheptane, 1-iodo-2-(pentafluoroethyl)cycloheptane, 1-iodo-2-(heptafluoro-n-propyl)cycloheptane, 1-iodo-2-(heptafluoro- iso-propyl)cycloheptane, 1-iodo-2-(nonafluoro-n-butyl)cycloheptane, 1-iodo-2-(nonafluoro-sec-butyl)cycloheptane, 1-iodo-2-(undecafluoro-). n-pentyl)cycloheptane, 1-iodo-2-(undecafluoro-sec-pentyl)cycloheptane, 1-iodo-2-(nonafluorocyclopentyl)cycloheptane, 1-iodo-2-(tridecafluoro-) n-hexyl)cycloheptane, 1-iodo-2-(undecafluorocyclohexyl)cycloheptane, 1-iodo-2-(pentadecafluoro-n-heptyl)cycloheptane, 1-iodo-2-(heptadecafluoro) Examples include -n-octyl)cycloheptane, methyl (2-iodocycloheptyl)difluoroacetate, ethyl (2-iodocycloheptyl)difluoroacetate and the like.
本発明の一般式(5)で表される含フッ素化合物で、R4とR5が縮環して8員環を形成している化合物としては、具体的には例えば、1−ヨード−2−(トリフルオロメチル)シクロオクタン、1−ヨード−2−(ペンタフルオロエチル)シクロオクタン、1−ヨード−2−(ヘプタフルオロ−n−プロピル)シクロオクタン、1−ヨード−2−(ヘプタフルオロ−iso−プロピル)シクロオクタン、1−ヨード−2−(ノナフルオロ−n−ブチル)シクロオクタン、1−ヨード−2−(ノナフルオロ−sec−ブチル)シクロオクタン、1−ヨード−2−(ウンデカフルオロ−n−ペンチル)シクロオクタン、1−ヨード−2−(ウンデカフルオロ−sec−ペンチル)シクロオクタン、1−ヨード−2−(ノナフルオロシクロペンチル)シクロオクタン、1−ヨード−2−(トリデカフルオロ−n−ヘキシル)シクロオクタン、1−ヨード−2−(ウンデカフルオロシクロヘキシル)シクロオクタン、1−ヨード−2−(ペンタデカフルオロ−n−ヘプチル)シクロオクタン、1−ヨード−2−(ヘプタデカフルオロ−n−オクチル)シクロオクタン、(2−ヨードシクロオクチル)ジフルオロ酢酸メチル、(2−ヨードシクロオクチル)ジフルオロ酢酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (5) of the present invention, in which R 4 and R 5 are condensed to form an 8-membered ring, include 1-iodo-2. -(Trifluoromethyl)cyclooctane, 1-iodo-2-(pentafluoroethyl)cyclooctane, 1-iodo-2-(heptafluoro-n-propyl)cyclooctane, 1-iodo-2-(heptafluoro- iso-propyl)cyclooctane, 1-iodo-2-(nonafluoro-n-butyl)cyclooctane, 1-iodo-2-(nonafluoro-sec-butyl)cyclooctane, 1-iodo-2-(undecafluoro- n-pentyl)cyclooctane, 1-iodo-2-(undecafluoro-sec-pentyl)cyclooctane, 1-iodo-2-(nonafluorocyclopentyl)cyclooctane, 1-iodo-2-(tridecafluoro- n-hexyl)cyclooctane, 1-iodo-2-(undecafluorocyclohexyl)cyclooctane, 1-iodo-2-(pentadecafluoro-n-heptyl)cyclooctane, 1-iodo-2-(heptadecafluoro) Examples include -n-octyl)cyclooctane, methyl (2-iodocyclooctyl)difluoroacetate, and ethyl (2-iodocyclooctyl)difluoroacetate.
本発明の一般式(6)で表される含フッ素化合物で、R8がn−ヘキシル基である化合物としては、具体的には例えば、(E/Z)−1,1,1−トリフルオロ−3−ヨード−2−ノネン、(E/Z)−1,1,1,2,2−ペンタフルオロ−4−ヨード−3−デセン、(E/Z)−1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨード−4−ウンデセン、(E/Z)−1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−ヨード−3−デセン、(E/Z)−1,1,1,2,2,3,3,4,4−ノナフルオロ−6−ヨード−5−ドデセン、(E/Z)−1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−ヨード−4−ウンデセン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−ヨード−6−トリデセン、(E/Z)−1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−ヨード−5−ドデセン、(E/Z)−1−(ノナフルオロシクロペンチル)−2−ヨード−1−オクテン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨード−7−テトラデセン、(E/Z)−1−(ウンデカフルオロシクロヘキシル)−2−ヨード−1−オクテン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−ヨード−8−ペンタデセン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−ヨード−9−ヘキサデセン、(E/Z)−2,2−ジフルオロ−3−ヨード−3−デセン酸メチル、(E/Z)−2,2−ジフルオロ−3−ヨード−3−デセン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (6) of the present invention in which R 8 is an n-hexyl group include (E/Z)-1,1,1-trifluoro. -3-iodo-2-nonene, (E/Z)-1,1,1,2,2-pentafluoro-4-iodo-3-decene, (E/Z)-1,1,1,2, 2,3,3-heptafluoro-5-iodo-4-undecene, (E/Z)-1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-iodo-3-decene, (E/Z)-1,1,1,2,2,3,3,4,4-nonafluoro-6-iodo-5-dodecene, (E/Z)-1,1,1,2,2,2 3-hexafluoro-3-(trifluoromethyl)-5-iodo-4-undecene, 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-7-iodo -6-Tridecene, (E/Z)-1,1,1,2,2,3,3,4-octafluoro-4-(trifluoromethyl)-6-iodo-5-dodecene, (E/Z )-1-(Nonafluorocyclopentyl)-2-iodo-1-octene, (E/Z)-1,1,1,2,2,3,3,4,4,5,5,6,6- Tridecafluoro-8-iodo-7-tetradecene, (E/Z)-1-(undecafluorocyclohexyl)-2-iodo-1-octene, (E/Z)-1,1,1,2,2 , 3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-iodo-8-pentadecene, (E/Z)-1,1,1,2,2,3 , 3,4,4,5,5,6,6,7,7,8,8-Heptadecafluoro-10-iodo-9-hexadecene, (E/Z)-2,2-difluoro-3-iodo Examples include methyl-3-decenoate, ethyl (E/Z)-2,2-difluoro-3-iodo-3-decenoate and the like.
本発明の一般式(6)で表される含フッ素化合物で、R8がn−ヘプチル基である化合物としては、具体的には例えば、(E/Z)−1,1,1−トリフルオロ−3−ヨード−2−デセン、(E/Z)−1,1,1,2,2−ペンタフルオロ−4−ヨード−3−ウンデセン、(E/Z)−1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨード−4−ドデセン、(E/Z)−1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−ヨード−3−ウンデセン、(E/Z)−1,1,1,2,2,3,3,4,4−ノナフルオロ−6−ヨード−5−トリデセン、(E/Z)−1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−ヨード−4−ドデセン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−ヨード−6−テトラデセン、(E/Z)−1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−ヨード−5−トリデセン、(E/Z)−1−(ノナフルオロシクロペンチル)−2−ヨード−1−ノネン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨード−7−ペンタデセン、(E/Z)−1−(ウンデカフルオロシクロヘキシル)−2−ヨード−1−ノネン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−ヨード−8−ヘキサデセン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−ヨード−9−ヘプタデセン、(E/Z)−2,2−ジフルオロ−3−ヨード−3−ドデセン酸メチル、(E/Z)−2,2−ジフルオロ−3−ヨード−3−ドデセン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (6) of the present invention in which R 8 is an n-heptyl group include (E/Z)-1,1,1-trifluoro. -3-iodo-2-decene, (E/Z)-1,1,1,2,2-pentafluoro-4-iodo-3-undecene, (E/Z)-1,1,1,2, 2,3,3-heptafluoro-5-iodo-4-dodecene, (E/Z)-1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-iodo-3-undecene, (E/Z)-1,1,1,2,2,3,3,4,4-nonafluoro-6-iodo-5-tridecene, (E/Z)-1,1,1,2,2, 3-hexafluoro-3-(trifluoromethyl)-5-iodo-4-dodecene, 1,1,1,2,2,3,4,4,5,5-undecafluoro-7-iodo -6-tetradecene, (E/Z)-1,1,1,2,2,3,3,4-octafluoro-4-(trifluoromethyl)-6-iodo-5-tridecene, (E/Z )-1-(Nonafluorocyclopentyl)-2-iodo-1-nonene, (E/Z)-1,1,1,2,2,3,3,4,5,5,6,6- Tridecafluoro-8-iodo-7-pentadecene, (E/Z)-1-(undecafluorocyclohexyl)-2-iodo-1-nonene, (E/Z)-1,1,1,2,2 , 3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-iodo-8-hexadecene, (E/Z)-1,1,1,2,2,3 , 3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-iodo-9-heptadecene, (E/Z)-2,2-difluoro-3-iodo Examples thereof include methyl-3-dodecenoate and ethyl (E/Z)-2,2-difluoro-3-iodo-3-dodecenoate.
本発明の一般式(6)で表される含フッ素化合物で、R8がn−オクチル基である化合物としては、具体的には例えば、(E/Z)−1,1,1−トリフルオロ−3−ヨード−2−ウンデセン、(E/Z)−1,1,1,2,2−ペンタフルオロ−4−ヨード−3−ドデセン、(E/Z)−1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨード−4−トリデセン、(E/Z)−1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−ヨード−3−ドデセン、(E/Z)−1,1,1,2,2,3,3,4,4−ノナフルオロ−6−ヨード−5−テトラデセン、(E/Z)−1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−ヨード−4−トリデセン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−ヨード−6−ペンタデセン、(E/Z)−1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−ヨード−5−テトラデセン、(E/Z)−1−(ノナフルオロシクロペンチル)−2−ヨード−1−デセン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨード−7−ヘキサデセン、(E/Z)−1−(ウンデカフルオロシクロヘキシル)−2−ヨード−1−デセン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−ヨード−8−ヘプタデセン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−ヨード−9−オクタデセン、(E/Z)−2,2−ジフルオロ−3−ヨード−3−トリデセン酸メチル、(E/Z)−2,2−ジフルオロ−3−ヨード−3−トリデセン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (6) of the present invention in which R 8 is an n-octyl group include (E/Z)-1,1,1-trifluoro. -3-iodo-2-undecene, (E/Z)-1,1,1,2,2-pentafluoro-4-iodo-3-dodecene, (E/Z)-1,1,1,2, 2,3,3-heptafluoro-5-iodo-4-tridecene, (E/Z)-1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-iodo-3-dodecene, (E/Z)-1,1,1,2,2,3,3,4,4-nonafluoro-6-iodo-5-tetradecene, (E/Z)-1,1,1,2,2, 3-hexafluoro-3-(trifluoromethyl)-5-iodo-4-tridecene, 1,1,1,2,2,3,4,4,5,5-undecafluoro-7-iodo -6-Pentadecene, (E/Z)-1,1,1,2,2,3,3,4-octafluoro-4-(trifluoromethyl)-6-iodo-5-tetradecene, (E/Z )-1-(Nonafluorocyclopentyl)-2-iodo-1-decene, (E/Z)-1,1,1,2,2,3,3,4,5,5,6,6- Tridecafluoro-8-iodo-7-hexadecene, (E/Z)-1-(undecafluorocyclohexyl)-2-iodo-1-decene, (E/Z)-1,1,1,2,2 , 3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-iodo-8-heptadecene, (E/Z)-1,1,1,2,2,3 ,3,4,4,5,5,6,6,7,7,8,8-Heptadecafluoro-10-iodo-9-octadecene, (E/Z)-2,2-difluoro-3-iodo Examples include methyl-3-tridecenoate, ethyl (E/Z)-2,2-difluoro-3-iodo-3-tridecenoate and the like.
本発明の一般式(6)で表される含フッ素化合物で、R8がn−ノニル基である化合物としては、具体的には例えば、(E/Z)−1,1,1−トリフルオロ−3−ヨード−2−ドデセン、(E/Z)−1,1,1,2,2−ペンタフルオロ−4−ヨード−3−トリデセン、(E/Z)−1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨード−4−テトラデセン、(E/Z)−1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−ヨード−3−トリデセン、(E/Z)−1,1,1,2,2,3,3,4,4−ノナフルオロ−6−ヨード−5−ペンタデセン、(E/Z)−1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−ヨード−4−テトラデセン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−ヨード−6−ヘキサデセン、(E/Z)−1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−ヨード−5−ペンタデセン、(E/Z)−1−(ノナフルオロシクロペンチル)−2−ヨード−1−ウンデセン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨード−7−ヘプタデセン、(E/Z)−1−(ウンデカフルオロシクロヘキシル)−2−ヨード−1−ウンデセン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−ヨード−8−オクタデセン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−ヨード−9−ノナデセン、(E/Z)−2,2−ジフルオロ−3−ヨード−3−テトラデセン酸メチル、(E/Z)−2,2−ジフルオロ−3−ヨード−3−テトラデセン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (6) of the present invention in which R 8 is an n-nonyl group include (E/Z)-1,1,1-trifluoro. -3-iodo-2-dodecene, (E/Z)-1,1,1,2,2-pentafluoro-4-iodo-3-tridecene, (E/Z)-1,1,1,2, 2,3,3-heptafluoro-5-iodo-4-tetradecene, (E/Z)-1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-iodo-3-tridecene, (E/Z)-1,1,1,2,2,3,3,4,4-nonafluoro-6-iodo-5-pentadecene, (E/Z)-1,1,1,2,2, 3-hexafluoro-3-(trifluoromethyl)-5-iodo-4-tetradecene, 1,1,1,2,2,3,4,4,5,5-undecafluoro-7-iodo -6-hexadecene, (E/Z)-1,1,1,2,2,3,3,4-octafluoro-4-(trifluoromethyl)-6-iodo-5-pentadecene, (E/Z )-1-(Nonafluorocyclopentyl)-2-iodo-1-undecene, (E/Z)-1,1,1,2,2,3,3,4,4,5,5,6,6- Tridecafluoro-8-iodo-7-heptadecene, (E/Z)-1-(undecafluorocyclohexyl)-2-iodo-1-undecene, (E/Z)-1,1,1,2,2 , 3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-iodo-8-octadecene, (E/Z)-1,1,1,2,2,3 , 3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-iodo-9-nonadecene, (E/Z)-2,2-difluoro-3-iodo Examples thereof include methyl-3-tetradecenoate and ethyl (E/Z)-2,2-difluoro-3-iodo-3-tetradecenoate.
本発明の一般式(6)で表される含フッ素化合物で、R8がn−デシル基である化合物としては、具体的には例えば、(E/Z)−1,1,1−トリフルオロ−3−ヨード−2−トリデセン、(E/Z)−1,1,1,2,2−ペンタフルオロ−4−ヨード−3−テトラデセン、(E/Z)−1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨード−4−ペンタデセン、(E/Z)−1,1,1,2−テトラフルオロ−2−(トリフルオロメチル)−4−ヨード−3−テトラデセン、(E/Z)−1,1,1,2,2,3,3,4,4−ノナフルオロ−6−ヨード−5−ヘキサデセン、(E/Z)−1,1,1,2,2,3−ヘキサフルオロ−3−(トリフルオロメチル)−5−ヨード−4−ペンタデセン、1,1,1,2,2,3,3,4,4,5,5−ウンデカフルオロ−7−ヨード−6−ヘプタデセン、(E/Z)−1,1,1,2,2,3,3,4−オクタフルオロ−4−(トリフルオロメチル)−6−ヨード−5−ヘキサデセン、(E/Z)−1−(ノナフルオロシクロペンチル)−2−ヨード−1−ドデセン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨード−7−オクタデセン、(E/Z)−1−(ウンデカフルオロシクロヘキシル)−2−ヨード−1−ドデセン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−ヨード−8−ノナデセン、(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタデカフルオロ−10−ヨード−9−イコセン、(E/Z)−2,2−ジフルオロ−3−ヨード−3−ペンタデセン酸メチル、(E/Z)−2,2−ジフルオロ−3−ヨード−3−ペンタデセン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (6) of the present invention in which R 8 is an n-decyl group include (E/Z)-1,1,1-trifluoro. -3-iodo-2-tridecene, (E/Z)-1,1,1,2,2-pentafluoro-4-iodo-3-tetradecene, (E/Z)-1,1,1,2, 2,3,3-heptafluoro-5-iodo-4-pentadecene, (E/Z)-1,1,1,2-tetrafluoro-2-(trifluoromethyl)-4-iodo-3-tetradecene, (E/Z)-1,1,1,2,2,3,3,4,4-nonafluoro-6-iodo-5-hexadecene, (E/Z)-1,1,1,2,2, 3-hexafluoro-3-(trifluoromethyl)-5-iodo-4-pentadecene, 1,1,1,2,2,3,4,4,5,5-undecafluoro-7-iodo -6-heptadecene, (E/Z)-1,1,1,2,2,3,3,4-octafluoro-4-(trifluoromethyl)-6-iodo-5-hexadecene, (E/Z) )-1-(Nonafluorocyclopentyl)-2-iodo-1-dodecene, (E/Z)-1,1,1,2,2,3,3,4,4,5,5,6,6- Tridecafluoro-8-iodo-7-octadecene, (E/Z)-1-(undecafluorocyclohexyl)-2-iodo-1-dodecene, (E/Z)-1,1,1,2,2 , 3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-iodo-8-nonadecene, (E/Z)-1,1,1,2,2,3 , 3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-iodo-9-icosene, (E/Z)-2,2-difluoro-3-iodo Examples include methyl-3-pentadecenoate, ethyl (E/Z)-2,2-difluoro-3-iodo-3-pentadecenoate, and the like.
本発明の一般式(6)で表される含フッ素化合物で、R8が2−ヒドロキシエチル基である化合物としては、具体的には例えば、(E/Z)−5,5,5−トリフルオロ−3−ヨード−3−ペンテン−1−オール、(E/Z)−5,5,6,6,6−ペンタフルオロ−3−ヨード−3−ヘキセン−1−オール、(E/Z)−5,5,6,6,7,7,7−ヘプタフルオロ−3−ヨード−3−ヘプテン−1−オール、(E/Z)−5,6,6,6−テトラフルオロ−5−(トリフルオロメチル)−3−ヨード−3−ヘキセン−1−オール、(E/Z)−5,5,6,6,7,7,8,8,8−ノナフルオロ−3−ヨード−3−オクテン−1−オール、(E/Z)−5,6,6,7,7,7−ヘキサフルオロ−5−(トリフルオロメチル)−3−ヨード−3−ヘプテン−1−オール、(E/Z)−5,5,6,6,7,7,8,8,9,9,9−ウンデカフルオロ−3−ヨード−3−ノネン−1−オール、(E/Z)−5,6,6,7,7,8,8,8−オクタフルオロ−5−(トリフルオロメチル)−3−ヨード−3−オクテン−1−オール、(E/Z)−4−(ノナフルオロシクロペンチル)−3−ヨード−3−ブテン−1−オール、(E/Z)−5,5,6,6,7,7,8,8,9,9,10,10,10−トリデカフルオロ−3−ヨード−3−デセン−1−オール、(E/Z)−4−(ウンデカフルオロシクロヘキシル)−3−ヨード−3−ブテン−1−オール、(E/Z)−5,5,6,6,7,7,8,8,9,9,10,10,11,11,11−ペンタデカフルオロ−3−ヨード−3−ウンデセン−1−オール、(E/Z)−5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12−ヘプタデカフルオロ−3−ヨード−3−ドデセン−1−オール、(E/Z)−2,2−ジフルオロ−4−ヨード−6−ヒドロキシ−3−ヘキセン酸メチル、(E/Z)−2,2−ジフルオロ−4−ヨード−6−ヒドロキシ−3−ヘキセン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (6) of the present invention in which R 8 is a 2-hydroxyethyl group include (E/Z)-5,5,5-tri Fluoro-3-iodo-3-penten-1-ol, (E/Z)-5,5,6,6,6-pentafluoro-3-iodo-3-hexen-1-ol, (E/Z) -5,5,6,6,7,7,7-heptafluoro-3-iodo-3-hepten-1-ol, (E/Z)-5,6,6,6-tetrafluoro-5-( Trifluoromethyl)-3-iodo-3-hexen-1-ol, (E/Z)-5,5,6,7,7,8,8,8-nonafluoro-3-iodo-3-octene -1-ol, (E/Z)-5,6,6,7,7,7-hexafluoro-5-(trifluoromethyl)-3-iodo-3-hepten-1-ol, (E/Z )-5,5,6,6,7,7,8,8,9,9,9-undecafluoro-3-iodo-3-nonen-1-ol, (E/Z)-5,6,6. 6,7,7,8,8,8-Octafluoro-5-(trifluoromethyl)-3-iodo-3-octen-1-ol, (E/Z)-4-(nonafluorocyclopentyl)-3 -Iodo-3-buten-1-ol, (E/Z)-5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluoro-3-iodo -3-decen-1-ol, (E/Z)-4-(undecafluorocyclohexyl)-3-iodo-3-buten-1-ol, (E/Z)-5, 5, 6, 6, 7,7,8,8,9,9,10,10,11,11,11-pentadecafluoro-3-iodo-3-undecen-1-ol, (E/Z)-5, 5, 6, 6,7,7,8,8,9,9,10,10,11,11,12,12,12-heptadecafluoro-3-iodo-3-dodecen-1-ol, (E/Z)- Examples include methyl 2,2-difluoro-4-iodo-6-hydroxy-3-hexenoate and ethyl (E/Z)-2,2-difluoro-4-iodo-6-hydroxy-3-hexenoate.
本発明の一般式(6)で表される含フッ素化合物で、R8が3−ヒドロキシ−n−プロピル基である化合物としては、具体的には例えば、(E/Z)−6,6,6−トリフルオロ−4−ヨード−4−ヘキセン−1−オール、(E/Z)−6,6,7,7,7−ペンタフルオロ−4−ヨード−4−ヘプテン−1−オール、(E/Z)−6,6,7,7,8,8,8−ヘプタフルオロ−4−ヨード−4−オクテン−1−オール、(E/Z)−6,7,7,7−テトラフルオロ−6−(トリフルオロメチル)−4−ヨード−4−ヘプテン−1−オール、(E/Z)−6,6,7,7,8,8,9,9,9−ノナフルオロ−4−ヨード−4−ノネン−1−オール、(E/Z)−6,7,7,8,8,8−ヘキサフルオロ−6−(トリフルオロメチル)−4−ヨード−4−オクテン−1−オール、(E/Z)−6,6,7,7,8,8,9,9,10,10,10−ウンデカフルオロ−4−ヨード−4−デセン−1−オール、(E/Z)−6,7,7,8,8,9,9,9−オクタフルオロ−6−(トリフルオロメチル)−4−ヨード−4−ノネン−1−オール、(E/Z)−5−(ノナフルオロシクロペンチル)−4−ヨード−4−ペンテン−1−オール、(E/Z)−6,6,7,7,8,8,9,9,10,10,11,11,11−トリデカフルオロ−4−ヨード−4−ウンデセン−1−オール、(E/Z)−5−(ウンデカフルオロシクロヘキシル)−4−ヨード−4−ペンテン−1−オール、(E/Z)−6,6,7,7,8,8,9,9,10,10,11,11,12,12,12−ペンタデカフルオロ−4−ヨード−4−ドデセン−1−オール、(E/Z)−6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13−ヘプタデカフルオロ−4−ヨード−4−トリデセン−1−オール、(E/Z)−2,2−ジフルオロ−4−ヨード−7−ヒドロキシ−3−ヘプテン酸メチル、(E/Z)−2,2−ジフルオロ−4−ヨード−7−ヒドロキシ−3−ヘプテン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (6) of the present invention in which R 8 is a 3-hydroxy-n-propyl group include (E/Z)-6,6,6. 6-trifluoro-4-iodo-4-hexen-1-ol, (E/Z)-6,6,7,7,7-pentafluoro-4-iodo-4-hepten-1-ol, (E /Z)-6,6,7,7,8,8,8-heptafluoro-4-iodo-4-octen-1-ol, (E/Z)-6,7,7,7-tetrafluoro- 6-(trifluoromethyl)-4-iodo-4-hepten-1-ol, (E/Z)-6,6,7,7,8,8,9,9,9-nonafluoro-4-iodo- 4-nonen-1-ol, (E/Z)-6,7,7,8,8,8-hexafluoro-6-(trifluoromethyl)-4-iodo-4-octen-1-ol, ( E/Z)-6,6,7,7,8,8,9,9,10,10,10-undecafluoro-4-iodo-4-decen-1-ol, (E/Z)-6 , 7,7,8,8,9,9,9-octafluoro-6-(trifluoromethyl)-4-iodo-4-nonen-1-ol, (E/Z)-5-(nonafluorocyclopentyl )-4-Iodo-4-penten-1-ol, (E/Z)-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro- 4-iodo-4-undecen-1-ol, (E/Z)-5-(undecafluorocyclohexyl)-4-iodo-4-penten-1-ol, (E/Z)-6,6,7 , 7,8,8,9,9,10,10,11,11,12,12,12-pentadecafluoro-4-iodo-4-dodecen-1-ol, (E/Z)-6,6 , 7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-heptadecafluoro-4-iodo-4-tridecen-1-ol, (E/ Z)-2,2-difluoro-4-iodo-7-hydroxy-3-heptenoate methyl, (E/Z)-2,2-difluoro-4-iodo-7-hydroxy-3-heptenoate ethyl etc. Can be mentioned.
本発明の一般式(6)で表される含フッ素化合物で、R8が4−ヒドロキシ−n−ブチル基である化合物としては、具体的には例えば、(E/Z)−7,7,7−トリフルオロ−5−ヨード−5−ヘプテン−1−オール、(E/Z)−7,7,8,8,8−ペンタフルオロ−5−ヨード−5−オクテン−1−オール、(E/Z)−7,7,8,8,9,9,9−ヘプタフルオロ−5−ヨード−5−ノネン−1−オール、(E/Z)−7,8,8,8−テトラフルオロ−7−(トリフルオロメチル)−5−ヨード−5−オクテン−1−オール、(E/Z)−7,7,8,8,9,9,10,10,10−ノナフルオロ−5−ヨード−5−デセン−1−オール、(E/Z)−7,8,8,9,9,9−ヘキサフルオロ−7−(トリフルオロメチル)−5−ヨード−5−ノネン−1−オール、(E/Z)−7,7,8,8,9,9,10,10,11,11,11−ウンデカフルオロ−5−ヨード−5−ウンデセン−1−オール、(E/Z)−7,8,8,9,9,10,10,10−オクタフルオロ−7−(トリフルオロメチル)−5−ヨード−5−デセン−1−オール、(E/Z)−6−(ノナフルオロシクロペンチル)−5−ヨード−5−ヘキセン−1−オール、(E/Z)−7,7,8,8,9,9,10,10,11,11,12,12,12−トリデカフルオロ−5−ヨード−5−ドデセン−1−オール、(E/Z)−6−(ウンデカフルオロシクロヘキシル)−5−ヨード−5−ヘキセン−1−オール、(E/Z)−7,7,8,8,9,9,10,10,11,11,12,12,13,13,13−ペンタデカフルオロ−5−ヨード−5−トリデセン−1−オール、(E/Z)−7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,14−ヘプタデカフルオロ−5−ヨード−5−テトラデセン−1−オール、(E/Z)−2,2−ジフルオロ−4−ヨード−8−ヒドロキシ−3−オクテン酸メチル、(E/Z)−2,2−ジフルオロ−4−ヨード−8−ヒドロキシ−3−オクテン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (6) of the present invention in which R 8 is a 4-hydroxy-n-butyl group include (E/Z)-7,7, 7-trifluoro-5-iodo-5-hepten-1-ol, (E/Z)-7,7,8,8,8-pentafluoro-5-iodo-5-octen-1-ol, (E /Z)-7,7,8,8,9,9,9-heptafluoro-5-iodo-5-nonen-1-ol, (E/Z)-7,8,8,8-tetrafluoro- 7-(trifluoromethyl)-5-iodo-5-octen-1-ol, (E/Z)-7,7,8,8,9,9,10,10,10-nonafluoro-5-iodo- 5-decen-1-ol, (E/Z)-7,8,8,9,9,9-hexafluoro-7-(trifluoromethyl)-5-iodo-5-nonen-1-ol, ( E/Z)-7,7,8,8,9,9,10,10,11,11,11-undecafluoro-5-iodo-5-undecen-1-ol, (E/Z)-7. ,8,8,9,9,10,10,10-octafluoro-7-(trifluoromethyl)-5-iodo-5-decen-1-ol, (E/Z)-6-(nonafluorocyclopentyl )-5-Iodo-5-hexen-1-ol, (E/Z)-7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluoro- 5-iodo-5-dodecen-1-ol, (E/Z)-6-(undecafluorocyclohexyl)-5-iodo-5-hexen-1-ol, (E/Z)-7,7,8 , 8,9,9,10,10,11,11,12,12,13,13,13-pentadecafluoro-5-iodo-5-tridecen-1-ol, (E/Z)-7,7 , 8,8,9,9,10,10,11,11,12,12,13,13,14,14,14-heptadecafluoro-5-iodo-5-tetradecen-1-ol, (E/ Z)-2,2-difluoro-4-iodo-8-hydroxy-3-octenoate methyl, (E/Z)-2,2-difluoro-4-iodo-8-hydroxy-3-octenoate ethyl, etc. Can be mentioned.
本発明の一般式(6)で表される含フッ素化合物で、R8が5−ヒドロキシ−n−ペンチル基である化合物としては、具体的には例えば、(E/Z)−8,8,8−トリフルオロ−6−ヨード−6−オクテン−1−オール、(E/Z)−8,8,9,9,9−ペンタフルオロ−6−ヨード−6−ノネン−1−オール、(E/Z)−8,8,9,9,10,10,10−ヘプタフルオロ−6−ヨード−6−デセン−1−オール、(E/Z)−8,9,9,9−テトラフルオロ−8−(トリフルオロメチル)−6−ヨード−6−ノネン−1−オール、(E/Z)−8,8,9,9,10,10,11,11,11−ノナフルオロ−6−ヨード−6−ウンデセン−1−オール、(E/Z)−8,9,9,10,10,10−ヘキサフルオロ−8−(トリフルオロメチル)−6−ヨード−6−デセン−1−オール、(E/Z)−8,8,9,9,10,10,11,11,12,12,12−ウンデカフルオロ−6−ヨード−6−ドデセン−1−オール、(E/Z)−8,9,9,10,10,11,11,11−オクタフルオロ−8−(トリフルオロメチル)−6−ヨード−6−ウンデセン−1−オール、(E/Z)−7−(ノナフルオロシクロペンチル)−6−ヨード−6−ヘプテン−1−オール、(E/Z)−8,8,9,9,10,10,11,11,12,12,13,13,13−トリデカフルオロ−6−ヨード−6−トリデセン−1−オール、(E/Z)−7−(ウンデカフルオロシクロヘキシル)−6−ヨード−6−ヘプテン−1−オール、(E/Z)−8,8,9,9,10,10,11,11,12,12,13,13,14,14,14−ペンタデカフルオロ−6−ヨード−6−テトラデセン−1−オール、(E/Z)−8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,15−ヘプタデカフルオロ−6−ヨード−6−ペンタデセン−1−オール、(E/Z)−2,2−ジフルオロ−4−ヨード−9−ヒドロキシ−3−ノネン酸メチル、(E/Z)−2,2−ジフルオロ−4−ヨード−9−ヒドロキシ−3−ノネン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (6) of the present invention in which R 8 is a 5-hydroxy-n-pentyl group include (E/Z)-8,8, 8-trifluoro-6-iodo-6-octen-1-ol, (E/Z)-8,8,9,9,9-pentafluoro-6-iodo-6-nonen-1-ol, (E /Z)-8,8,9,9,10,10,10-heptafluoro-6-iodo-6-decen-1-ol, (E/Z)-8,9,9,9-tetrafluoro- 8-(trifluoromethyl)-6-iodo-6-nonen-1-ol, (E/Z)-8,8,9,9,10,10,11,11,11-nonafluoro-6-iodo- 6-undecen-1-ol, (E/Z)-8,9,9,10,10,10-hexafluoro-8-(trifluoromethyl)-6-iodo-6-decen-1-ol, ( E/Z)-8,8,9,9,10,10,11,11,12,12,12-undecafluoro-6-iodo-6-dodecen-1-ol, (E/Z)-8 , 9,9,10,10,11,11,11-octafluoro-8-(trifluoromethyl)-6-iodo-6-undecen-1-ol, (E/Z)-7-(nonafluorocyclopentyl )-6-Iodo-6-hepten-1-ol, (E/Z)-8,8,9,9,10,10,11,11,12,12,13,13,13-tridecafluoro- 6-iodo-6-tridecen-1-ol, (E/Z)-7-(undecafluorocyclohexyl)-6-iodo-6-hepten-1-ol, (E/Z)-8,8,9 , 9,10,10,11,11,12,12,13,13,14,14,14-pentadecafluoro-6-iodo-6-tetradecen-1-ol, (E/Z)-8,8 , 9,9,10,10,11,11,12,12,13,13,14,14,15,15,15-heptadecafluoro-6-iodo-6-pentadecen-1-ol, (E/ Z)-2,2-difluoro-4-iodo-9-hydroxy-3-nonenate, ethyl (E/Z)-2,2-difluoro-4-iodo-9-hydroxy-3-nonenate, etc. Can be mentioned.
本発明の一般式(6)で表される含フッ素化合物で、R8が5−ヒドロキシ−n−ヘキシル基である化合物としては、具体的には例えば、(E/Z)−9,9,9−トリフルオロ−7−ヨード−7−ノネン−1−オール、(E/Z)−9,9,10,10,10−ペンタフルオロ−7−ヨード−7−デセン−1−オール、(E/Z)−9,9,10,10,11,11,11−ヘプタフルオロ−7−ヨード−7−ウンデセン−1−オール、(E/Z)−9,10,10,10−テトラフルオロ−9−(トリフルオロメチル)−7−ヨード−7−デセン−1−オール、(E/Z)−9,9,10,10,11,11,12,12,12−ノナフルオロ−7−ヨード−7−ドデセン−1−オール、(E/Z)−9,10,10,11,11,11−ヘキサフルオロ−9−(トリフルオロメチル)−7−ヨード−7−ウンデセン−1−オール、(E/Z)−9,9,10,10,11,11,12,12,13,13,13−ウンデカフルオロ−7−ヨード−7−トリデセン−1−オール、(E/Z)−9,10,10,11,11,12,12,12−オクタフルオロ−9−(トリフルオロメチル)−7−ヨード−7−ドデセン−1−オール、(E/Z)−8−(ノナフルオロシクロペンチル)−7−ヨード−7−オクテン−1−オール、(E/Z)−9,9,10,10,11,11,12,12,13,13,14,14,14−トリデカフルオロ−7−ヨード−7−テトラデセン−1−オール、(E/Z)−8−(ウンデカフルオロシクロヘキシル)−7−ヨード−7−オクテン−1−オール、(E/Z)−9,9,10,10,11,11,12,12,13,13,14,14,15,15,15−ペンタデカフルオロ−7−ヨード−7−ペンタデセン−1−オール、(E/Z)−9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,16−ヘプタデカフルオロ−7−ヨード−7−ヘキサデセン−1−オール、(E/Z)−2,2−ジフルオロ−4−ヨード−10−ヒドロキシ−3−デセン酸メチル、(E/Z)−2,2−ジフルオロ−4−ヨード−10−ヒドロキシ−3−デセン酸エチル等が挙げられる。 Specific examples of the fluorine-containing compound represented by the general formula (6) of the present invention in which R 8 is a 5-hydroxy-n-hexyl group include (E/Z)-9,9, 9-trifluoro-7-iodo-7-nonen-1-ol, (E/Z)-9,9,10,10,10-pentafluoro-7-iodo-7-decen-1-ol, (E /Z)-9,9,10,10,11,11,11-heptafluoro-7-iodo-7-undecen-1-ol, (E/Z)-9,10,10,10-tetrafluoro- 9-(trifluoromethyl)-7-iodo-7-decen-1-ol, (E/Z)-9,9,10,10,11,11,12,12,12-nonafluoro-7-iodo- 7-dodecen-1-ol, (E/Z)-9,10,10,11,11,11-hexafluoro-9-(trifluoromethyl)-7-iodo-7-undecen-1-ol, ( E/Z)-9,9,10,10,11,11,12,12,13,13,13-undecafluoro-7-iodo-7-tridecen-1-ol, (E/Z)-9. , 10,10,11,11,12,12,12-octafluoro-9-(trifluoromethyl)-7-iodo-7-dodecen-1-ol, (E/Z)-8-(nonafluorocyclopentyl )-7-Iodo-7-octen-1-ol, (E/Z)-9,9,10,10,11,11,12,12,13,13,14,14,14-tridecafluoro- 7-iodo-7-tetradecen-1-ol, (E/Z)-8-(undecafluorocyclohexyl)-7-iodo-7-octen-1-ol, (E/Z)-9,9,10 , 10,11,11,12,12,13,13,14,14,15,15,15-pentadecafluoro-7-iodo-7-pentadecen-1-ol, (E/Z)-9,9 , 10,10,11,11,12,12,13,13,14,14,15,15,16,16,16-heptadecafluoro-7-iodo-7-hexadecen-1-ol, (E/ Z)-2,2-difluoro-4-iodo-10-hydroxy-3-decenoic acid methyl ester, (E/Z)-2,2-difluoro-4-iodo-10-hydroxy-3-decenoic acid ethyl ester, etc. Can be mentioned.
本発明に適用可能なアミン類としては、具体的には例えば、ジエチルアミン、トリエチルアミン、ジイソプロピルアミン、N,N−ジイソプロピルエチルアミン、ベンジルアミン、N−メチルベンジルアミン、N,N−ジメチルベンジルアミン、N−エチルベンジルアミン、N,N−ジエチルペンジルアミン、ピロリジン、N−メチルピロリジン、ピペリジン、N−メチルピペリジン、N−エチルピペリジン、ピペラジン、N−メチルピペラジン、N,N´−ジメチルピペラジン、N−エチルピペラジン、N,N´−ジエチルピペラジン等が挙げられる。 Specific examples of amines applicable to the present invention include diethylamine, triethylamine, diisopropylamine, N,N-diisopropylethylamine, benzylamine, N-methylbenzylamine, N,N-dimethylbenzylamine and N-. Ethylbenzylamine, N,N-diethylpentylamine, pyrrolidine, N-methylpyrrolidine, piperidine, N-methylpiperidine, N-ethylpiperidine, piperazine, N-methylpiperazine, N,N'-dimethylpiperazine, N-ethylpiperazine , N,N′-diethylpiperazine and the like.
本発明の実施に当たっては、光源としては、通常の外光(太陽光)、般用の蛍光灯、小型蛍光灯(CFLランプ)、市販の化学実験用の発光ダイオード(LED)を用いることが可能である。LEDについては種類としては、青色LED、白色LED及び赤色LEDの3種が購入、取得できるが、本発明にはどのLEDでも適用可能である。 In carrying out the present invention, as the light source, it is possible to use ordinary outside light (sunlight), general fluorescent lamps, small fluorescent lamps (CFL lamps), and commercially available light emitting diodes (LEDs) for chemical experiments. Is. As for the type of LED, three types of blue LED, white LED and red LED can be purchased and acquired, but any type of LED is applicable to the present invention.
本発明の一般式(1)で表されるエナミン誘導体の使用量は、反応に具する一般式(2)で表されるオレフィン類又は一般式(3)で表されるアセチレン類に対して0.001モル量〜0.6モル量使用するとよく、さらに0.005モル量〜0.2モル量、特に0.005モル量〜0.15モル量使用するとよい。 The use amount of the enamine derivative represented by the general formula (1) of the present invention is 0 with respect to the olefin represented by the general formula (2) or the acetylene represented by the general formula (3) used in the reaction. It is preferable to use 0.001 to 0.6 molar amount, more preferably 0.005 to 0.2 molar amount, particularly 0.005 to 0.15 molar amount.
本発明に適用可能なアミン類の使用量は、反応に具する一般式(2)で表されるオレフィン類又は一般式(3)で表されるアセチレン類に対して、0.001モル量〜1.000モル量使用するとよい。 The amount of amines applicable to the present invention is 0.001 mol amount to the olefins represented by the general formula (2) or the acetylenes represented by the general formula (3) used in the reaction. It is advisable to use an amount of 1.000 mol.
本発明の一般式(5)で表される含フッ素ヨウ素化合物の使用量としては、反応に具する一般式(2)で表されるオレフィン類又は一般式(3)で表されるアセチレン類に対して、理論的には等モル量の使用で反応が実施可能であるが、反応成績を安定させるため、1.05モル量〜5.00モル量の使用が好ましい。 The use amount of the fluorine-containing iodine compound represented by the general formula (5) of the present invention is as follows: olefins represented by the general formula (2) or acetylenes represented by the general formula (3) used in the reaction. On the other hand, theoretically, the reaction can be carried out by using an equimolar amount, but in order to stabilize the reaction results, it is preferable to use 1.05 to 5.00 mol amount.
本発明に適用可能な有機溶剤は、反応に不活性なものであれば特に制約はないが、具体的には例えば、塩化メチレン、アセトニトリル、テトラヒドロフラン、ジオキサン等が挙げられ、反応に具する一般式(2)で表されるオレフィン類又は一般式(3)で表されるアセチレン類に対して10重量倍量〜1,000重量倍量使用するとよい。 The organic solvent applicable to the present invention is not particularly limited as long as it is inert to the reaction, and specific examples thereof include methylene chloride, acetonitrile, tetrahydrofuran, dioxane, and the like. It is advisable to use 10-fold by weight to 1,000-fold by weight of the olefins represented by (2) or the acetylenes represented by the general formula (3).
本発明の反応温度及び時間としては、反応に具する一般式(2)で表されるオレフィン類又は一般式(3)で表されるアセチレン類の種類、エナミン類の種類、アミン類の種類及び含フッ素有機ヨウ化物の種類により異なるが、通常0℃〜60℃の温度範囲で、2時間〜48時間反応を行うことにより、反応は完結できる。 The reaction temperature and time of the present invention include the types of olefins represented by the general formula (2) or the acetylenes represented by the general formula (3), enamines, amines and The reaction can be completed by carrying out the reaction for 2 hours to 48 hours usually in the temperature range of 0° C. to 60° C., although it varies depending on the type of the fluorine-containing organic iodide.
本発明の反応後の後処理としては、周知の方法であれば特に規定はないが、例えば、エーテル等の溶剤で抽出、硫酸ナトリウム上で乾燥、ろ過、濃縮し粗製物を得、シリカゲルカラムクロマトグラフィー等により精製し、目的物の一般式(5)または一般式(6)で表わされる含フッ素化合物を得ることができる。 The post-treatment after the reaction of the present invention is not particularly limited as long as it is a well-known method, for example, extraction with a solvent such as ether, drying over sodium sulfate, filtration, concentration to obtain a crude product, silica gel column chromatography Purification by chromatography or the like can give the target fluorine-containing compound represented by the general formula (5) or the general formula (6).
以下実施例により本発明を具体的に説明するが、本発明はこれらの実施例のみに限定されるものではない。 Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited to these examples.
なお分析に当たっては下記機器を使用した。
1H−NMR,19F−NMR,13C−NMR:日本電子(株)製GSX−400スペクトロメーター(JEOL GSX−400 spectrometer)。
HRMS:日本電子(株)製JMS−700スペクトロメーター(JEOL JMS−700 (FAB))。
IR:日本分光(株)製FT/IR−4100スペクトロメーター(JASCO FT/IR−4100)。
The following equipment was used for the analysis.
1 H-NMR, 19 F-NMR, 13 C-NMR: JEOL GSX-400 spectrometer (JEOL GSX-400 spectrometer).
HRMS: JMS-700 spectrometer (JEOL JMS-700 (FAB)) manufactured by JEOL Ltd.
IR: FT/IR-4100 spectrometer manufactured by JASCO Corporation (JASCO FT/IR-4100).
また光源については、23W小型蛍光ランプ(CFLランプ)を用いた。 As the light source, a 23 W small fluorescent lamp (CFL lamp) was used.
参考例1 N−(2−メチル−3−フェニル−1−プロペン−1−イル)ピロリジン(6)の調製 Reference Example 1 Preparation of N-(2-methyl-3-phenyl-1-propen-1-yl)pyrrolidine (6)
撹拌子を備えた50mLのナス型フラスコに、2−メチル−3−フェニルプロパナール(11.3mg、0.075mmol、0.10equiv.)、ピロリジン(6μL、5.2mg、0.075mmol、0.10equiv.)、硫酸ナトリウム(1.0g)及びジクロロメタン(7.5mL)を仕込み、室温下、1時間反応を行った。
反応後、ろ過、濃縮することにより、目的物のN−(2−メチル−3−フェニル−1−プロペン−1−イル)ピロリジン(9)を得た。
In a 50 mL eggplant-shaped flask equipped with a stir bar, 2-methyl-3-phenylpropanal (11.3 mg, 0.075 mmol, 0.10 equiv.), pyrrolidine (6 μL, 5.2 mg, 0.075 mmol, 0. 10 equiv.), sodium sulfate (1.0 g) and dichloromethane (7.5 mL) were charged, and the reaction was carried out at room temperature for 1 hour.
After the reaction, filtration and concentration were performed to obtain N-(2-methyl-3-phenyl-1-propen-1-yl)pyrrolidine (9) as a target.
得られた目的物は無色透明液体であり、分析データは次の通りであった。
1H−NMRでの測定において、5.84ppmにエナミン由来のピークを確認した。
1H−NMR(400MHz,CDCl3)δ7.15−7.32(5H,m,Ph),5.84(1H,s),3.22(2H,s),3.02−3.06(4H,t,J=6.8Hz),1.78−1.80(4H,m),1.59−1.60(3H,d,J=1.2Hz)。
The obtained target product was a colorless transparent liquid, and the analytical data were as follows.
In 1 H-NMR measurement, a peak derived from an enamine was confirmed at 5.84 ppm.
1 H-NMR (400 MHz, CDCl 3 ) δ 7.15-7.32 (5 H, m, Ph), 5.84 (1 H, s), 3.22 (2 H, s), 3.02-3.06. (4H, t, J=6.8Hz), 1.78-1.80 (4H, m), 1.59-1.60 (3H, d, J=1.2Hz).
参考例2 N−(2−フェニル−1−プロピレン−1−イル)ピロリジン(8)の調製 Reference Example 2 Preparation of N-(2-phenyl-1-propylene-1-yl)pyrrolidine (8)
参考例1の2−メチル−3−フェニルプロパナールに替えて、2−フェニルプロパノールを用いた以外は実施例1と同じ操作を行い、目的物のN−(2−フェニル−1−プロピレン−1−イル)ピロリジン(8)を得た。 The same operation as in Example 1 was performed except that 2-phenyl-3-phenylpropanal in Reference Example 1 was used and 2-phenylpropanol was used, and N-(2-phenyl-1-propylene-1) of the target product was obtained. -Yl)pyrrolidine (8) was obtained.
得られた目的物は黄色液体であり、分析データは次の通りであった。
1H−NMRでの測定において、6.64ppmにエナミン由来のピークを確認した。
1H−NMR(400MHz,CDCl3)δ7.08−7.56(5H,m,Ph),6.43(1H,s),3.25−3.40(4H,m),2.11(3H,s),1.87− 1.93(4H,m)。
The obtained target product was a yellow liquid, and the analytical data were as follows.
In measurement by 1 H-NMR, a peak derived from enamine was confirmed at 6.64 ppm.
1 H-NMR (400 MHz, CDCl 3 ) δ 7.08-7.56 (5H, m, Ph), 6.43 (1H, s), 3.25-3.40 (4H, m), 2.11. (3H, s), 1.87-1.93 (4H, m).
参考例3 N−(2,2−ジフェニル−エチレン−1−イル)ピロリジン(9)の調製 Reference Example 3 Preparation of N-(2,2-diphenyl-ethylene-1-yl)pyrrolidine (9)
参考例1の2−メチル−3−フェニルプロパナールに替えて、2,2−ジフェニルアセトアルデヒドを用いた以外は実施例1と同じ操作を行い、目的物のN−(2−フェニル−1−プロピレン−1−イル)ピロリジン(9)を得た。 The same operation as in Example 1 was carried out except that 2,2-diphenylacetaldehyde was used instead of 2-methyl-3-phenylpropanal of Reference Example 1 to obtain the desired product N-(2-phenyl-1-propylene). -1-yl)pyrrolidine (9) was obtained.
得られた目的物は黄色液体であり、分析データは次の通りであった。
1H−NMRでの測定において、6.63ppmにエナミン由来のピークを確認した。
黄色液体。
1H−NMR(400MHz,CDCl3)δ7.28−7.01(10H,m,Ph),6.63(1H,s),2.99−2.95(4H,t,J=6.8Hz),1.73−1.68(4H,m)。
13C−NMR(126MHz,CDCl3)δ160.8,144.4,141.0,135.9,132.3,131.6,130.0,128.2,127.9,127.4,126.0,125.2,123.9,111.6,51.9(2C),25.4(2C)。
The obtained target product was a yellow liquid, and the analytical data were as follows.
In the 1 H-NMR measurement, a peak derived from an enamine was confirmed at 6.63 ppm.
Yellow liquid.
1 H-NMR (400 MHz, CDCl 3 ) δ 7.28-7.01 ( 10 H, m, Ph), 6.63 (1 H, s), 2.99-2.95 (4 H, t, J=6. 8 Hz), 1.73-1.68 (4H, m).
13 C-NMR (126 MHz, CDCl 3 ) δ160.8, 144.4, 141.0, 135.9, 132.3, 131.6, 130.0, 128.2, 127.9, 127.4, 13 . 126.0, 125.2, 123.9, 111.6, 51.9 (2C), 25.4 (2C).
参考例4 N−(2−フェニルエチレン−1−イル)ピロリジン(10)の調製 Reference Example 4 Preparation of N-(2-phenylethylene-1-yl)pyrrolidine (10)
参考例1の2−メチル−3−フェニルプロパナールに替えて、2−フェニルアセトアルデヒドを用いた以外は実施例1と同じ操作を行い、目的物のN−(2−フェニル−1−プロピレン−1−イル)ピロリジン(10)を得た。 The same operation as in Example 1 was performed except that 2-phenyl-3-phenylpropanal of Reference Example 1 was used and 2-phenylacetaldehyde was used, and N-(2-phenyl-1-propylene-1) of the target product was obtained. -Yl) pyrrolidine (10) was obtained.
得られた目的物は黄色液体であり、分析データは次の通りであった。
1H−NMRでの測定において、5.08ppm(J=14.0Hz)及び7.03ppm(J=14.0Hz)にエナミン由来のピークを確認した。
1H−NMR(400MHz,CDCl3)δ7.13−7.20(5H,m,Ph),7.02−7.05(1H,d,J=14.0Hz),5.06−5.10(1H,d,J=13.6Hz),3.20−3.23(4H,t,J=6.4Hz),1.80−1.91(4H,m)。
The obtained target product was a yellow liquid, and the analytical data were as follows.
In 1 H-NMR measurement, peaks derived from enamine were confirmed at 5.08 ppm (J=14.0 Hz) and 7.03 ppm (J=14.0 Hz).
1 H-NMR (400 MHz, CDCl 3 ) δ 7.13-7.20 (5 H, m, Ph), 7.02-7.05 (1 H, d, J=14.0 Hz), 5.06-5. 10 (1H, d, J=13.6Hz), 3.20-3.23 (4H, t, J=6.4Hz), 1.80-1.91 (4H, m).
実施例1 1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の調製 Example 1 Preparation of 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11)
撹拌子を備えた20mLの二口ナス型フラスコに、参考例3で調製したN−(2,2−ジフェニル−エチレン−1−イル)ピロリジン(9)(124.7mg,0.50mmol,0.50equiv.)を添加し、アルゴン置換した後、これにジクロロメタン(10mL)、1−デセン(140.3mg,1.00mmol)及びピロリジン(35.6mg,0.50mol,0.50equiv.)及び1−ヨード−トルデカフルオロヘキサン(490.5mg,1.10mmol,1.10equiv.)を仕込み、室温下、攪拌しながら、23W−CFLランプにより光照射を16時間行った。反応終了後、エバポレ−タ−により濃縮し粗製物を得、次いでカラムクロマトグラフィー(ヘキサン)による精製を行い、目的物の1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)を得た(521.7mg,0.89mmol,収率89%)。 In a 20 mL two-necked eggplant-shaped flask equipped with a stir bar, N-(2,2-diphenyl-ethylene-1-yl)pyrrolidine (9) prepared in Reference Example 3 (124.7 mg, 0.50 mmol, 0. 50 equiv.) was added and the atmosphere was replaced with argon. Then, dichloromethane (10 mL), 1-decene (140.3 mg, 1.00 mmol) and pyrrolidine (35.6 mg, 0.50 mol, 0.50 equiv.) and 1- Iodo-torudecafluorohexane (490.5 mg, 1.10 mmol, 1.10 equiv.) was charged, and light irradiation was performed with a 23 W-CFL lamp for 16 hours at room temperature with stirring. After the completion of the reaction, the product was concentrated by an evaporator to obtain a crude product, which was then purified by column chromatography (hexane) to obtain 1,1,1,2,2,3,3,4,4,5. , 5,6,6-Tridecafluoro-8-iodohexadecane (11) was obtained (521.7 mg, 0.89 mmol, yield 89%).
分析データは次の通りであった。
無色透明液体。
1H−NMR(400MHz,CDCl3)δ4.33(1H,tt,J=4.4,8.8Hz),2.88(1H,m),2.77(1H,m),1.80(2H,m),1.36−1.43(12H,m),0.89(3H,t,J=6.4Hz)。
13C−NMR(126MHz,CDCl3)δ41.7(t,J=21.6Hz),40.3,31.8,29.5,29.3,29.2,28.5,22.6,20.9,14.1。
19F−NMR(376MHz,CDCl3)δ−81.3(3F),−112.3(1F,d,J=277.1Hz),−115.1(1F,d,J=277.1Hz),−122.3(2F),−123.4(2F),−124.1(2F),−126.6(2F)。
IR(neat,cm−1)2928,2857,1238,1145。
HRMS(FAB+) calcd for C16H20F13I [M−H]−: 585.0324,Found: 585.0334。
The analytical data were as follows.
Colorless transparent liquid.
1 H-NMR (400 MHz, CDCl 3 ) δ 4.33 (1 H, tt, J=4.4, 8.8 Hz), 2.88 (1 H, m), 2.77 (1 H, m), 1.80. (2H,m), 1.36-1.43 (12H,m), 0.89 (3H,t, J=6.4Hz).
13 C-NMR (126 MHz, CDCl 3 ) δ41.7 (t, J=21.6 Hz), 40.3, 31.8, 29.5, 29.3, 29.2, 28.5, 22.6. , 20.9, 14.1.
19 F-NMR (376 MHz, CDCl 3 ) δ-81.3 (3F), -112.3 (1F, d, J=277.1 Hz), -115.1 (1F, d, J=277.1 Hz). , -122.3 (2F), -123.4 (2F), -124.1 (2F), -126.6 (2F).
IR(neat, cm< -1 >) 2928, 2857, 1238, 1145.
HRMS (FAB +) calcd for C 16 H 20 F 13 I [M-H] -: 585.0324, Found: 585.0334.
実施例2 1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の調製
実施例1と同じ反応装置を用い、ピロリジン(35.6mg,0.50mol,0.50equiv.)の使用量を、7.1mg(0.10mmol、0.10equiv.)とした以外、実施例1と同じ操作を行い、目的物の1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)を得た(586.2mg,1.00mmol,収率quant.)。
Example 2 Preparation of 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) The same reactor as in Example 1 was used. Except that the used amount of pyrrolidine (35.6 mg, 0.50 mol, 0.50 equiv.) was 7.1 mg (0.10 mmol, 0.10 equiv.). 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) was obtained (586.2 mg, 1.00 mmol, Yield quant.).
実施例3 1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の調製
実施例1と同じ反応装置を用い、N−(2,2−ジフェニル−エチレン−1−イル)ピロリジン(11)(124.7mg,0.50mmol,0.50equiv.)の使用量を、24.7mg(0.10mmol、0.10equiv.)、ピロリジン(35.6mg,0.50mol,0.50equiv.)の使用量を、3.6mg(0.05mmol、0.05equiv.)とした以外、実施例1と同じ操作を行い、目的物の1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)を得た(586.2mg,1.00mmol,収率quant.)。
Example 3 Preparation of 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) The same reactor as in Example 1 was used. The amount of N-(2,2-diphenyl-ethylene-1-yl)pyrrolidine (11) (124.7 mg, 0.50 mmol, 0.50 equiv.) used was 24.7 mg (0.10 mmol, 0.10 mmol). 10 equiv.) and pyrrolidine (35.6 mg, 0.50 mol, 0.50 equiv.) were used in the same manner as in Example 1 except that the amount used was 3.6 mg (0.05 mmol, 0.05 equiv.), As a result, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) was obtained (586.2 mg, 1. 00 mmol, yield quant.).
実施例4 1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の調製
撹拌子を備えた20mLの二口ナス型フラスコに、参考例3で調製したN−(2,2−ジフェニル−エチレン−1−イル)ピロリジン(9)(2.5mg,0.01mmol,0.01equiv.)を添加し、アルゴン置換した後、これにジクロロメタン(10mL)、1−デセン(140.3mg,1.00mmol)及びピロリジン(0.7mg,0.01mol,0.01equiv.)及び1−ヨード−トルデカフルオロヘキサン(490.5mg,1.10mmol,1.10equiv.)を仕込み、室温下、攪拌しながら、23W−CFLランプにより光照射を16時間行った。反応終了後、エバポレ−タ−により濃縮し粗製物を得、次いでカラムクロマトグラフィー(ヘキサン)による精製を行い、目的物の1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)を得た(521.7mg,0.82mmol,収率82%)。
Example 4 Preparation of 1,1,1,2,2,3,3,4,5,5,5,6,6-tridecafluoro-8-iodohexadecane (11) 20 mL of a distiller equipped with a stir bar. N-(2,2-diphenyl-ethylene-1-yl)pyrrolidine (9) (2.5 mg, 0.01 mmol, 0.01 equiv.) prepared in Reference Example 3 was added to a necked eggplant-shaped flask, and argon was added. After substitution, this was replaced with dichloromethane (10 mL), 1-decene (140.3 mg, 1.00 mmol) and pyrrolidine (0.7 mg, 0.01 mol, 0.01 equiv.) and 1-iodo-torudecafluorohexane (490 0.5 mg, 1.10 mmol, 1.10 equiv.) was charged and light irradiation was carried out for 16 hours at room temperature while stirring with a 23 W-CFL lamp. After completion of the reaction, the product was concentrated by an evaporator to obtain a crude product, and then purified by column chromatography (hexane) to obtain 1,1,1,2,2,3,3,4,4,5. , 5,6,6-Tridecafluoro-8-iodohexadecane (11) was obtained (521.7 mg, 0.82 mmol, yield 82%).
実施例5〜8 1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の調製
実施例4と同じ反応装置を用い、表1中に示した条件を変更した以外は実施例4と同じ操作を行い、目的物の1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)を得た。結果を表1中に示した。
Examples 5-8 Preparation of 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) Same reaction as in Example 4 Using the apparatus, the same operation as in Example 4 was carried out except that the conditions shown in Table 1 were changed to obtain 1, 1, 1, 2, 2, 3, 3, 4, 4, 5, 5, the target product. 6,6-Tridecafluoro-8-iodohexadecane (11) was obtained. The results are shown in Table 1.
比較例1 1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の調製
実施例4と同じ反応装置を用い、ピロリジン(2.5mg,0.01mol,0.01equiv.)を添加せず実施例4と同じ操作を行ったところ、目的物1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の生成は確認されなかった。
Comparative Example 1 Preparation of 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) The same reactor as in Example 4 was used. When the same operation as in Example 4 was carried out without using pyrrolidine (2.5 mg, 0.01 mol, 0.01 equiv.), the desired product 1,1,1,2,2,3,3,4, was obtained. Formation of 4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) was not confirmed.
参考例5 1 1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の調製
撹拌子を備えた50mLのナス型フラスコに、参考例4で調製した2,2−ジフェニル−1−(ピロリジン−1−イル)エチレン(9)(167.6mg、0.60mmol、0.8equiv.)、1−デセン(104.6mg、0.75mmol)、トリデカフルオロ−1−ヨードヘキサン(n−C6F13I、180μL、371.3mg、0.83mmol、1.1equiv.)及びジクロロメタン(7.5mL)を仕込み、室温下、攪拌しながら23 W−CFLランプによる光照射を16時間行った。反応後、濃縮し、粗製物を得、次いで、カラムクロマトグラフィーによる精製(展開溶液 へキサン:エ−テル=2:1)を行い、目的物の1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)を無色透明液体として得た(440.0mg、0.75mmol、収率quant.)。
Reference Example 5 1 Preparation of 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) 50 mL equipped with a stir bar In an eggplant-shaped flask, 2,2-diphenyl-1-(pyrrolidin-1-yl)ethylene (9) (167.6 mg, 0.60 mmol, 0.8 equiv.) prepared in Reference Example 4 and 1-decene (104) were prepared. .6mg, 0.75mmol), tridecafluoro-1-iodo-hexane (n-C 6 F 13 I , 180μL, 371.3mg, 0.83mmol, 1.1equiv.) were charged in dichloromethane (7.5 mL), Irradiation with a 23 W-CFL lamp was performed for 16 hours at room temperature with stirring. After the reaction, the reaction mixture is concentrated to obtain a crude product, which is then purified by column chromatography (developing solution hexane:ether=2:1) to obtain the desired product 1,1,1,2,2,3,3. 3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) was obtained as a colorless transparent liquid (440.0 mg, 0.75 mmol, yield quant.).
参考例6 1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の調製
撹拌子を備えた50mLのナス型フラスコに、2−メチル−3−フェニルプロパナール(11.3mg、0.075mmol、0.10equiv.)、ピロリジン(6μL、5.2mg、0.075mmol、0.10equiv.)、1−デセン(104.6mg、0.75mmol)、トリデカフルオロ−1−ヨードヘキサン(n−C6F13I、180μL、371.3mg、0.83mmol、1.1equiv.)及びジクロロメタン(7.5mL)を仕込み、室温下、攪拌しながら23 W CFLランプによる光照射を16時間行った。反応後、濃縮し、粗製物を得え、次いで、カラムクロマトグラフィーによる精製(展開溶液 へキサン:エ−テル=2:1)を行い、目的物の1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)を無色透明液体として得た(290.1mg、0.50mmol、収率66%)。
Reference Example 6 Preparation of 1,1,1,2,2,3,3,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) 50 mL eggplant equipped with a stir bar In a mold flask, 2-methyl-3-phenylpropanal (11.3 mg, 0.075 mmol, 0.10 equiv.), pyrrolidine (6 μL, 5.2 mg, 0.075 mmol, 0.10 equiv.), 1-decene ( charged 104.6mg, 0.75mmol), tridecafluoro-1-iodo-hexane (n-C 6 F 13 I , 180μL, 371.3mg, 0.83mmol, 1.1equiv.) and dichloromethane (7.5 mL) At room temperature, light irradiation with a 23 W CFL lamp was performed for 16 hours while stirring. After the reaction, the reaction product is concentrated to obtain a crude product, which is then purified by column chromatography (developing solution hexane:ether=2:1) to obtain 1,1,1,2,2,3 of the desired product. , 3,4,4,5,5,6,6-Tridecafluoro-8-iodohexadecane (11) was obtained as a colorless transparent liquid (290.1 mg, 0.50 mmol, yield 66%).
参考例7〜9 1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の調製
参考例6と同じ反応装置を用い、2−メチル−3−フェニルプロパナール(11.3mg、0.075mmol、0.10equiv.)を、表2中に示したアルデヒドに替えた以外、実施例3と同じ操作を行い、目的物の1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)を得た。結果を表2中に示した。
Reference Examples 7 to 9 Preparation of 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) Same Reaction as Reference Example 6 Using the apparatus, the same operation as in Example 3 was performed, except that 2-methyl-3-phenylpropanal (11.3 mg, 0.075 mmol, 0.10 equiv.) was replaced with the aldehyde shown in Table 2, As a result, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) was obtained. The results are shown in Table 2.
参考例10〜12 1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の調製
参考例6と同じ反応装置を用い、ジフェニルアセトアルデヒド(Ph2CHCHO)及びピロリジンの使用量を表3中に示した量に替えた以外、参考例6と同じ操作を行い、目的物の1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)を得た。結果を表3中に示した。
Reference Examples 10 to 12 Preparation of 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) Same reaction as Reference Example 6 Using the apparatus, the same operation as in Reference Example 6 was performed except that the amounts of diphenylacetaldehyde (Ph 2 CHO) and pyrrolidine used were changed to the amounts shown in Table 3, to obtain 1,1,1,2,2 of the target compound. , 3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) was obtained. The results are shown in Table 3.
参考例13 1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の調製
撹拌子を備えた50mLのナス型フラスコに、2−フェニルプロパナール(31.9mg、0.25mmol、0.90equiv.)、(S)−2−[ビス(3,4−ジメトキシフェニル)メトキシメチル]ピロリジン(193.1mg、0.53mmol、1.90equiv.)、1−デセン(35.6mg、0.28mmol)、トリデカフルオロ−1−ヨードヘキサン(n−C6F13I、60μL、123.5mg、0.28mmol、1.0equiv.)及びジクロロメタン(2.8mL)を仕込み、室温下、攪拌しながら23W−CFLランプによる光照射を16時間行った。反応後、濃縮し、粗製物を得え、次いで、カラムクロマトグラフィーによる精製(展開溶液 へキサン:エ−テル=2:1)を行い、目的物の1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)を無色透明液体として得た(193.0mg、0.28mmol、収率quant.)。
Reference Example 13 Preparation of 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) 50 mL eggplant equipped with a stir bar In a mold flask, 2-phenylpropanal (31.9 mg, 0.25 mmol, 0.90 equiv.), (S)-2-[bis(3,4-dimethoxyphenyl)methoxymethyl]pyrrolidine (193.1 mg, 0). .53mmol, 1.90equiv.), 1- decene (35.6mg, 0.28mmol), tridecafluoro-1-iodo-hexane (n-C 6 F 13 I , 60μL, 123.5mg, 0.28mmol, 1 0.0 equiv.) and dichloromethane (2.8 mL) were charged, and light irradiation with a 23 W-CFL lamp was performed for 16 hours at room temperature with stirring. After the reaction, the reaction product is concentrated to obtain a crude product, which is then purified by column chromatography (developing solution hexane:ether=2:1) to obtain 1,1,1,2,2,3 of the desired product. , 3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) was obtained as a colorless transparent liquid (193.0 mg, 0.28 mmol, yield quant.).
参考例14 1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)の調製
参考例13と同じ反応装置を用い、参考例13の2−フェニルプロパナール(31.9mg、0.25mmol、0.90equiv.)に替えてジフェニルアセトアルデヒド(49.0mg、0.25mmol、0.90equiv.)を用いた以外、参考例13と同じ操作を行い、目的物の1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨードヘキサデカン(11)を無色透明液体として得た(185.9.0mg、0.28mmol、収率quant.)。
Reference Example 14 Preparation of 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) The same reactor as in Reference Example 13 was used. Other than using, except that diphenylacetaldehyde (49.0 mg, 0.25 mmol, 0.90 equiv.) was used instead of 2-phenylpropanal (31.9 mg, 0.25 mmol, 0.90 equiv.) of Reference Example 13. The same operation as in Example 13 was carried out to obtain 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane (11) as a colorless product. Obtained as a transparent liquid (185.9.0 mg, 0.28 mmol, yield quant.).
参考例15 3,3,4,4,5,5,6,6,7,7,8,8,9,9,9−ペンタデカフルオロ−1−フェニル−1−ヨードオクタン(12)の調製 Reference Example 15 Preparation of 3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-pentadecafluoro-1-phenyl-1-iodooctane (12)
撹拌子を備えた50mLのナス型フラスコに、ジフェニルアセトアルデヒド(49.0mg、0.25mmol、1.0equiv.)、ピロリジン(44μL、37.9mg、0.525mmol)、スチレン(29μL、26.3mg、0.25mmol)、トリデカフルオロ−1−ヨードヘキサン(n−C6F13I、60μL、123.8mg、0.28mmol、1.1equiv.)及びジクロロメタン(2.5mL)を仕込み、室温下、攪拌しながら23 W CFLランプによる光照射を16時間行った。反応後、濃縮し、粗製物を得え、次いで、カラムクロマトグラフィーによる精製(展開溶液 へキサン:エ−テル=2:1)を行い、目的物の3,3,4,4,5,5,6,6,7,7,8,8,9,9,9−トリデカフルオロ−1−フェニル−1−ヨードオクタン(12)を無色透明液体として得た(33.3mg、0.06mmol、収率24%)。 In a 50 mL eggplant-shaped flask equipped with a stir bar, diphenylacetaldehyde (49.0 mg, 0.25 mmol, 1.0 equiv.), pyrrolidine (44 μL, 37.9 mg, 0.525 mmol), styrene (29 μL, 26.3 mg, 0.25 mmol), tridecafluoro-1-iodo-hexane (n-C 6 F 13 I , 60μL, 123.8mg, 0.28mmol, 1.1equiv.) were charged in dichloromethane (2.5 mL), at room temperature, Light irradiation with a 23 W CFL lamp was performed for 16 hours while stirring. After the reaction, the reaction product is concentrated to obtain a crude product, which is then purified by column chromatography (developing solution hexane:ether=2:1) to obtain 3,3,4,4,5,5 of the desired product. , 6,6,7,7,8,8,9,9,9-tridecafluoro-1-phenyl-1-iodooctane (12) was obtained as a colorless transparent liquid (33.3 mg, 0.06 mmol, Yield 24%).
分析データは次の通りであった。
1H−NMR(400MHz,CDCl3)δ7.31−7.50(5H,Ph),5.21−5.24(1H,q),2.58−2.69(1H,m),2.38−2.49(1H,m)。
19F−NMR(376MHz,CDCl3)δ−81.3(3F,s),−112.5−−114.7(2F,q,J=288.8Hz),−122.3(2F,s),−123.4(2F,s),−124.2(2F,s),−126.6 2F,s)。
The analytical data were as follows.
1 H-NMR (400 MHz, CDCl 3 ) δ7.31-7.50 (5H, Ph), 5.21-5.24 (1H, q), 2.58-2.69 (1H, m), 2 .38-2.49 (1H, m).
19 F-NMR (376 MHz, CDCl 3 ) δ-81.3 (3F, s), -112.5--114.7 (2F, q, J=288.8 Hz), -122.3 (2F, s). ), -123.4 (2F, s), -124.2 (2F, s), -126.6 2F, s).
参考例16〜25 各種オレフィン類とn−C6F13Iの反応
参考例15と同じ反応装置を用い、スチレンに替えて表4又は表5中に示したオレフィン類を用い、表4又は表5中に示した条件下、反応を行った。なお、溶剤ジクロロメタンの使用量は、オレフィン類0.1mmolに対して1.0mLの比率で使用し、反応は室温下、16時間反応を行った。結果を表4又は表5中に示した。
Using the same reactor as the reaction in Reference Example 15 Reference Example 16 to 25 Various olefins and n-C 6 F 13 I, instead of styrene with olefins shown in Table 4 or Table 5, Table 4 or Table The reaction was carried out under the conditions shown in 5. The solvent dichloromethane was used at a ratio of 1.0 mL to 0.1 mmol of olefins, and the reaction was carried out at room temperature for 16 hours. The results are shown in Table 4 or Table 5.
1)3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−1,2−ジフェニ−1−ヨードルエタン(13)
無色透明液体。
1H−NMR(400MHz,CDCl3)δ7.27−7.50(5H,Ph),3.12−3.21(2H,t,J=18.4Hz)。
19F−NMR(376MHz,CDCl3)δ−81.3(3F,s),−109.5(2F,s),−122.1(2F,s),−123.4(2F,s),−124.1(2F,s),−126.6(2F,s)。
1) 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1,2-diphenyl-1-iodolethane (13)
Colorless transparent liquid.
1 H-NMR (400MHz, CDCl 3) δ7.27-7.50 (5H, Ph), 3.12-3.21 (2H, t, J = 18.4Hz).
19 F-NMR (376 MHz, CDCl 3 ) δ-81.3 (3F, s), -109.5 (2F, s), -122.1 (2F, s), -123.4 (2F, s). , -124.1 (2F, s), -126.6 (2F, s).
2)1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−メチル−8−ヨードドデカン(14)
無色透明液体。
1H−NMR(400MHz,CDCl3)δ2.96−3.02(2H,m),2.20−2.23(3H,d,J=1.6Hz),1.71−1.84(2H,m),1.46−1.61(2H,m),1.36−1.43(2H,m),0.92−0.96(3H,t)。
19F−NMR(376MHz,CDCl3)δ−81.3(3F,s),−110.7−−112.7(2F,q,J=277.1Hz),−122.1(2F,s),−123.4(2F,s),−124.1(2F,s),−126.6(2F,s)。
2) 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-methyl-8-iodododecane (14)
Colorless transparent liquid.
1 H-NMR (400 MHz, CDCl 3 ) δ 2.96-3.02 (2 H, m), 2.20-2.23 (3 H, d, J=1.6 Hz), 1.71-1.84 ( 2H,m), 1.46-1.61 (2H,m), 1.36-1.43 (2H,m), 0.92-0.96 (3H,t).
19 F-NMR (376 MHz, CDCl 3 ) δ-81.3 (3F, s), -110.7--112.7 (2F, q, J=277.1 Hz), -122.1 (2F, s). ), -123.4 (2F, s), -124.1 (2F, s), -126.6 (2F, s).
3)7,7,8,8,9,9,10,10,11,11,12,12,12−トリデカフルオロ−5−ヨード−1−ドデカノール(15)
無色透明液体。
1H−NMR(400MHz,CDCl3)δ4.34(1H,tt,J=4.8,8.0Hz),3.68(2H,t,J=6.4Hz),2.91(1H,m),2.80(1H,m),2.78−2.93(2H,m),1.47−1.90(6H,m)。
13C−NMR(126MHz,CDCl3)δ62.5,41.6(t,J=20.4Hz),40.0,31.5,26.0,20.4。
19F−NMR(376MHz,CDCl3)δ−81.3(3F),−111.7−−115.5(2F,dd,J=277.5Hz,1103.3Hz),−122.3(2F),−123.4(2F),−124.1(2F),−126.6(2F)。
IR(neat,cm−1)3336,2938,2865,1237,1204,1058。
HRMS (ESI−) calcd for C12H11OF13I[M−H]:544.9647.Found:544.9657。
3) 7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluoro-5-iodo-1-dodecanol (15)
Colorless transparent liquid.
1 H-NMR (400 MHz, CDCl 3 ) δ 4.34 (1 H, tt, J=4.8, 8.0 Hz), 3.68 (2 H, t, J=6.4 Hz), 2.91 (1 H, m), 2.80 (1H, m), 2.78-2.93 (2H, m), 1.47-1.90 (6H, m).
13 C-NMR (126 MHz, CDCl 3 ) δ62.5, 41.6 (t, J=20.4 Hz), 40.0, 31.5, 26.0, 20.4.
19 F-NMR (376 MHz, CDCl 3 ) δ-81.3 (3F), -111.7--115.5 (2F, dd, J=277.5 Hz, 1103.3 Hz), -122.3 (2F). ), -123.4 (2F), -124.1 (2F), -126.6 (2F).
IR(neat, cm< -1 >) 3336, 2938, 2865, 1237, 1204, 1058.
HRMS (ESI -) calcd for C 12 H 11 OF 13 I [M-H]: 544.9647. Found: 544.9657.
4)1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−メチル−8−ヨードトリデカン(16)
無色透明液体。
Colorless oil。
1H−NMR(400MHz,CDCl3)δ4.73−4.75(1H,qd,J=2.4Hz,4.8Hz),4.59−4.62(1H,d,J=12.0Hz),4.35−4.38(1H,t,J=4.0Hz),2.88−3.00(1H,m),2.60−2.67(1H,t,J=16.8Hz),1.97−1.99(3H,d,J=7.2Hz),1.85−1.87(3H,d,J=7.2Hz),1.39−1.40(3H,d,J=7.2Hz),1.26−1.28(3H,d,J=7.2Hz),1.30−1.37(6H,m),0.88−0.94(3H,m)。
19F−NMR(376MHz,CDCl3)δ−81.3(3F,s),−110.5−−118.3(diastereomer mixture,2F,dd),−121.4(2F,s),−122.4(2F,s),−123.3(2F,s),−126.6(2F,s)。
4) 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-7-methyl-8-iodotridecane (16)
Colorless transparent liquid.
Colorless oil.
1 H-NMR (400 MHz, CDCl 3 ) δ 4.73-4.75 (1 H, qd, J=2.4 Hz, 4.8 Hz), 4.59-4.62 (1 H, d, J=12.0 Hz) ), 4.35-4.38 (1H, t, J=4.0Hz), 2.88-3.00 (1H, m), 2.60-2.67 (1H, t, J=16. 8Hz), 1.97-1.99 (3H, d, J=7.2Hz), 1.85-1.87 (3H, d, J=7.2Hz), 1.39-1.40 (3H). , D, J=7.2 Hz), 1.26-1.28 (3H, d, J=7.2 Hz), 1.30-1.37 (6H, m), 0.88-0.94( 3H, m).
19 F-NMR (376 MHz, CDCl 3 ) δ-81.3 (3F, s), -110.5--118.3 (diastereomer mixture, 2F, dd), -121.4 (2F, s), -. 122.4 (2F, s), -123.3 (2F, s), -126.6 (2F, s).
5)1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−7−エチル−8−ヨードデカン(17)
無色透明液体。
1H−NMR(400MHz,CDCl3)δ4.37−4.40(1H,d,J=11.2Hz),4.26−4.30(1H,qd,J=1.6Hz,3.2Hz),2.60−2.68(1H,t,J=15.2Hz),1.99−2.14(2H,m),1.85−1.92(2H,m,J=7.2Hz),1.69−1.87(2H,m),1.52−1.63(2H,m,J=7.2Hz),1.11−1.14(3H,t,J=7.2Hz),1.09−1.13(3H,t,J=7.2Hz),1.04−1.08(3H,t,J=7.2Hz),0.99−1.03(3H,t,J=7.2Hz)。
19F−NMR(376MHz,CDCl3)δ−80.8(3F,s),−109.6−−115.1(diastereomer mixture,2F,dd,J=288.8Hz,1473.4Hz),−121.8(2F,s),−122.7(2F,s),−126.2(2F,s)。
5) 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-7-ethyl-8-iododecane (17)
Colorless transparent liquid.
1 H-NMR (400 MHz, CDCl 3 ) δ4.37-4.40 (1H, d, J=11.2 Hz), 4.26-4.30 (1H, qd, J=1.6 Hz, 3.2 Hz). ), 2.60-2.68 (1H, t, J = 15.2Hz), 1.99-2.14 (2H, m), 1.85-1.92 (2H, m, J = 7.). 2Hz), 1.69-1.87 (2H, m), 1.52-1.63 (2H, m, J=7.2Hz), 1.11-1.14 (3H, t, J=7). .2 Hz), 1.09-1.13 (3H, t, J=7.2 Hz), 1.04-1.08 (3H, t, J=7.2 Hz), 0.99-1.03 ( 3H, t, J=7.2 Hz).
19 F-NMR (376 MHz, CDCl 3 ) δ-80.8 (3F, s), -109.6--115.1 (diastereomer mixture, 2F, dd, J=288.8 Hz, 1473.4 Hz), −. 121.8 (2F, s), -122.7 (2F, s), -126.2 (2F, s).
6)1−ヨード−2−(n−トリデカフルオロヘキシル)シクロヘプタン(18)
黄色液体。
1H−NMR(400MHz,CDCl3)δ4.95−4.99(1H,m,J=2.8Hz),4.90−4.91(1H,m),3.18−3.25(1H,m,J=10.4Hz),2.22−2.35(2H,m),1.95−1.98(2H,d,J=12.4Hz),1.79−1.90(6H,m),1.68−1.70(2H,d,J=12.4Hz),1.44−1.53(2H,m)。
19F−NMR(376MHz,CDCl3)δ−81.3(3F,s),−110.8−−118.7(diastereomer mixture,2F,dd,J=277.1Hz,2692.2Hz),−120.4(2F,s),−122.3(2F,s),−124.1(2F,s),−125.7−−127.5(2F,dd,J=288.8Hz,381.2Hz)。
6) 1-iodo-2-(n-tridecafluorohexyl)cycloheptane (18)
Yellow liquid.
1 H-NMR (400 MHz, CDCl 3 ) δ 4.95-4.99 (1 H, m, J=2.8 Hz), 4.90-4.91 (1 H, m), 3.18-3.25( 1H, m, J=10.4Hz), 2.22-2.35 (2H, m), 1.95-1.98 (2H, d, J=12.4Hz), 1.79-1.90. (6H, m), 1.68-1.70 (2H, d, J=12.4Hz), 1.44-1.53 (2H, m).
19 F-NMR (376MHz, CDCl 3) δ-81.3 (3F, s), - 110.8--118.7 (diastereomer mixture, 2F, dd, J = 277.1Hz, 2692.2Hz), - 120.4 (2F, s), -122.3 (2F, s), -124.1 (2F, s), -125.7--127.5 (2F, dd, J=288.8Hz, 381) .2 Hz).
7)1−ヨード−2−(n−トリデカフルオロヘキシル)シクロオクテン(19)
黄色液体。
1H−NMR(400MHz,CDCl3)δ4.61−4.64(1H,m),2.25−2.45(3H,m),2.02−2.15(2H,m),1.83−1.97(2H,m),1.41−1.74(7H,m)。
19F−NMR(376MHz,CDCl3)δ−81.3(3F,s),−115.8−−117.4(2F,q),−120.2(2F,s),−122.5(2F,s),−123.3(2F,s),−126.6(2F,s)。
7) 1-iodo-2-(n-tridecafluorohexyl)cyclooctene (19)
Yellow liquid.
1 H-NMR (400 MHz, CDCl 3 ) δ 4.61-4.64 (1 H, m), 2.25-2.45 (3 H, m), 2.02-2.15 (2 H, m), 1 0.83-1.97 (2H,m), 1.41-1.74 (7H,m).
19 F-NMR (376 MHz, CDCl 3 ) δ-81.3 (3F, s), -115.8--117.4 (2F, q), -120.2 (2F, s), -122.5. (2F, s), -123.3 (2F, s), -126.6 (2F, s).
1)4,4,5,5,6,6,7,7,8,8,9,9,9−トリデカフルオロ−2−メチル−2−ヨードノナン酸メチル(20)
黄色液体。
1H−NMR(400MHz,CDCl3)δ3.83(3H,s),2.47−2.77(2H,d,J=4.4Hz),1.52(3H,s)。
19F−NMR(376MHz,CDCl3)δ−81.3(3F),−110.6−−115.2(2F,dd,J=254.6Hz,1461.9Hz,288.8Hz),−115.1(1F,d,J=277.1Hz),−122.3(2F),−123.4(2F),−124.1(2F),−126.6(2F)。
1) Methyl 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-methyl-2-iodononanoate (20)
Yellow liquid.
1 H-NMR (400 MHz, CDCl 3 ) δ 3.83 (3H, s), 2.47-2.77 (2H, d, J=4.4 Hz), 1.52 (3H, s).
19 F-NMR (376 MHz, CDCl 3 ) δ-81.3 (3F), -110.6--115.2 (2F, dd, J=254.6 Hz, 1461.9 Hz, 288.8 Hz), -115. .1 (1F, d, J=277.1 Hz), -122.3 (2F), -123.4 (2F), -124.1 (2F), -126.6 (2F).
2)4,4,5,5,6,6,7,7,8,8,9,9,9−トリデカフルオロ−2−メチル−2−ヨードノナン酸(2−イソプロピルアダマンタン−2−イル)(21)
黄色液体。
19F−NMR(376MHz,CDCl3)δ−81.3(3F,s),−108.7−−114.3(2F,dd,J=288.8Hz,1798.4Hz,277.1Hz),−122.4(2F,s),−123.4(2F,s),−124.0(2F,s),−126.6(2F,s)。
2) 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-methyl-2-iodononanoic acid (2-isopropyladamantan-2-yl) (21)
Yellow liquid.
19 F-NMR (376 MHz, CDCl 3 ) δ-81.3 (3F, s), -108.7--114.3 (2F, dd, J=288.8 Hz, 1798.4 Hz, 277.1 Hz), -122.4 (2F, s), -123.4 (2F, s), -124.0 (2F, s), -126.6 (2F, s).
3)4,4,5,5,6,6,7,7,8,8,9,9,9−トリデカフルオロ−2−メチル−2−ヨードノナン酸(イソボルネン−2−イル)(22)
黄色液体。
19F−NMR(376MHz,CDCl3)δ−81.3(3F,s),−110.3−−114.8(2F,qd,J=69.6Hz,271.5Hz),−122.2(2F,s),−123.4(2F,s),−124.1−−124.3(2F,d,J=69.2Hz),−126.6(2F,s)。
3) 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-methyl-2-iodononanoic acid (isobornen-2-yl) (22)
Yellow liquid.
19 F-NMR (376 MHz, CDCl 3 ) δ-81.3 (3F, s), -110.3--114.8 (2F, qd, J=69.6 Hz, 271.5 Hz), -122.2. (2F, s), -123.4 (2F, s), -124.1--124.3 (2F, d, J=69.2Hz), -126.6 (2F, s).
参考例26〜27 各種アセチレン類とn−C6F13Iの反応
参考例15と同じ反応装置を用い、スチレンに替えて表6中に示したアセチレン類を用い、表5中に示した条件下、反応を行った。なお、溶剤ジクロロメタンの使用量は、オレフィン類0.1mmolに対して1.0mLの比率で使用し、反応は室温下、16時間反応を行った。結果を表6中に示した。
Using the same reactor as in Reference Example 26 to 27 Various acetylenes and n-C 6 F 13 The reaction in Reference Example 15 of I, with acetylenes shown in Table 6 instead of styrene, shown in Table 5 Conditions The reaction was performed below. The solvent dichloromethane was used at a ratio of 1.0 mL to 0.1 mmol of olefins, and the reaction was carried out at room temperature for 16 hours. The results are shown in Table 6.
1)(E/Z)−1,1,1,2,2,3,3,4,4,5,5,6,6−トリデカフルオロ−8−ヨード−7−ヘキサデセン(23)
無色透明液体。E/Z=94/6の混合物。
1H−NMR(400MHz,CDCl3)δ6.31(E−isomer,1H,t,J=14.8Hz),6.23(Z−isomer,1H,t,J=12.8Hz),2.66(Z−isomer,2H,t,J=7.6Hz),2.62(E−isomer,2H,t,J=8.0Hz),1.56(2H,m),1.28−1.30(10H,m),0.88(3H,t,J=6.4Hz)。
13C−NMR(126MHz,CDCl3)δ126.4(E−isomer,t,J=23.9Hz),123.1(E−isomer,t,J=5.9Hz),121.6(Z−isomer,t,J=24.0Hz),118.5(Z−isomer,t,J=6.0Hz),48.4(Z−isomer),41.1(E−isomer),31.78(E−isomer),31.77(Z−isomer),30.0(E−isomer),29.7(Z−isomer),29.2(E−isomer),29.11(Z−isomer),29.08(E−isomer),29.02(Z−isomer),28.4(E−isomer),28.0(Z−isomer),22.6,14.0。
19F−NMR(376MHz,CDCl3)δ−81.3(3F),−105.9(E−isomer,2F),−109.0(Z−isomer,2F),−122.2(2F),−123.4(2F),−123.8(2F),−126.6(2F)。
IR(neat,cm−1)2930,2858,1240,1145。
Anal. Calcd for C16H18F13I:C,32.90;H,3.11.Found:C,33.11;H,2.92。
1) (E/Z)-1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodo-7-hexadecene (23)
Colorless transparent liquid. Mixture of E/Z=94/6.
1 H-NMR (400 MHz, CDCl 3 ) δ 6.31 (E-somer, 1 H, t, J=14.8 Hz), 6.23 (Z-isomer, 1 H, t, J=12.8 Hz), 2. 66 (Z-isomer, 2H, t, J=7.6Hz), 2.62 (E-isomer, 2H, t, J=8.0Hz), 1.56 (2H, m), 1.28-1 30 (10H, m), 0.88 (3H, t, J=6.4Hz).
13 C-NMR (126 MHz, CDCl 3 ) δ126.4 (E-isomer, t, J=23.9 Hz), 123.1 (E-somer, t, J=5.9 Hz), 121.6 (Z- isomer, t, J=24.0 Hz), 118.5 (Z-somer, t, J=6.0 Hz), 48.4 (Z-somer), 41.1 (E-isomer), 31.78 ( E-somer), 31.77 (Z-somer), 30.0 (E-somer), 29.7 (Z-somer), 29.2 (E-somer), 29.11 (Z-somer), 29.08 (E-isomer), 29.02 (Z-isomer), 28.4 (E-isomer), 28.0 (Z-isomer), 22.6, 14.0.
19 F-NMR (376 MHz, CDCl 3 ) δ-81.3 (3F), -105.9 (E-isomer, 2F), -109.0 (Z-isomer, 2F), -122.2 (2F). , -123.4 (2F), -123.8 (2F), -126.6 (2F).
IR(neat, cm< -1 >) 2930,2858,1240,1145.
Anal. Calcd for C 16 H 18 F 13 I:C, 32.90; H, 3.11. Found: C, 33.11; H, 2.92.
2)(E/Z)−7,7,8,8,9,9,10,10,11,11,12,12,12−トリデカフルオロ−5−ヨード−5−ドデセン−1−オール(24)
黄色液体。E/Z=90/10の混合物。
1HNMR(400MHz,CDCl3)δ6.32−6.39(E−isomer,1H,t,J=14.8Hz),3.74−3.77(2H,t,J=5.6Hz),2.66−2.70(2H,m),1.55−1.73(4H,m)。
19F−NMR(376MHz,CDCl3)δ−81.3(3F),−105.7(E−isomer,2F,s),−108.8(Z−isomer,2F,s),−122.1(2F),−123.3(2F),−123.7(2F),−126.6(2F)。
2) (E/Z)-7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluoro-5-iodo-5-dodecen-1-ol( 24)
Yellow liquid. Mixture of E/Z=90/10.
1 HNMR (400 MHz, CDCl 3 ) δ 6.32-6.39 (E-isomer, 1 H, t, J=14.8 Hz), 3.74-3.77 (2H, t, J=5.6 Hz), 2.66-2.70 (2H,m), 1.55-1.73 (4H,m).
19 F-NMR (376 MHz, CDCl 3 ) δ-81.3 (3F), -105.7 (E-isomer, 2F, s), -108.8 (Z-isomer, 2F, s), -12. 1 (2F), -123.3 (2F), -123.7 (2F), -126.6 (2F).
参考例28〜31 1−デセンと各種含フッ素ヨウ素化合物の反応
参考例15と同じ反応装置を用い、スチレンに替えて1−デセンを用い、表7中に示した含フッ素ヨウ素化合物を用い、表7中に示した条件下、反応を行った。なお、溶剤ジクロロメタンの使用量は、オレフィン類0.1mmolに対して1.0mLの比率で使用し、反応は室温下、16時間反応を行った。結果を表7中に示した。
Reference Examples 28 to 31 Reaction of 1-decene with various fluorine-containing iodine compounds Using the same reaction apparatus as in Reference Example 15, 1-decene was used in place of styrene, and the fluorine-containing iodine compounds shown in Table 7 were used. The reaction was carried out under the conditions shown in 7. The solvent dichloromethane was used at a ratio of 1.0 mL to 0.1 mmol of olefins, and the reaction was carried out at room temperature for 16 hours. The results are shown in Table 7.
1)1,1,1,2,2,3,3−ヘプタフルオロ−5−ヨードトリデカン(25)
無色透明液体。
1HNMR(400MHz,CDCl3)δ4.33(1H,tt,J=4.4,8.8Hz),2.89(2H,m),1.80(2H,m),1.20−1.58(12H,m),0.90(3H,t,J=6.4Hz)。
19FNMR(376MHz,CDCl3)δ−81.1(3F),−112.8−−116.6(2F,dd,J=265.8Hz,1145.1Hz),−128.4(2F)。
1) 1,1,1,2,2,3,3-heptafluoro-5-iodotridecane (25)
Colorless transparent liquid.
1 HNMR (400 MHz, CDCl 3 ) δ 4.33 (1H, tt, J=4.4, 8.8 Hz), 2.89 (2H, m), 1.80 (2H, m), 1.20-1. 0.58 (12H, m), 0.90 (3H, t, J=6.4Hz).
19 FNMR (376 MHz, CDCl 3 ) δ-81.1 (3F), -112.8--116.6 (2F, dd, J=265.8 Hz, 1145.1 Hz), -128.4 (2F).
2)1,1,1,2,2,3,3,4,4−ノナフルオロ−6−ヨードテトラデカン(226)
無色透明液体。
1HNMR(400MHz,CDCl3)δ4.33(1H,tt,J=4.4,8.8Hz),2.89(1H,m),2.80(1H,m),1.80(2H,m),1.20−1.58(12H,m),0.90(3H,t,J=6.4Hz)。
13C−NMR(126MHz,CDCl3)δ41.6(t,J=21.6Hz),40.4,31.8,29.6,29.4,29.2,28.5,22.7,20.9,14.1。
19F−NMR(376MHz,CDCl3)δ−81.5(3F),−112.5(1F,d,J=265.9Hz),−115.3(1F,d,J=265.9Hz),−125.1(2F),−126.4(2F)。
IR(neat,cm−1)2928,2857,1235,1135。
Anal. Calcd for C14H20F9I:C,34.59;H,4.15.Found:C,34.38;H,4.47。
2) 1,1,1,2,2,3,3,4,4-nonafluoro-6-iodotetradecane (226)
Colorless transparent liquid.
1 H NMR (400 MHz, CDCl 3 ) δ 4.33 (1 H, tt, J=4.4, 8.8 Hz), 2.89 (1 H, m), 2.80 (1 H, m), 1.80 (2 H. , M), 1.20-1.58 (12H, m), 0.90 (3H, t, J=6.4Hz).
13 C-NMR (126 MHz, CDCl 3 ) δ41.6 (t, J=21.6 Hz), 40.4, 31.8, 29.6, 29.4, 29.2, 28.5, 22.7. , 20.9, 14.1.
19 F-NMR (376 MHz, CDCl 3 ) δ-81.5 (3F), -112.5 (1F, d, J=265.9 Hz), -115.3 (1F, d, J=265.9 Hz). , -125.1 (2F), -126.4 (2F).
IR(neat, cm< -1 >) 2928, 2857, 1235, 1135.
Anal. Calcd for C 14 H 20 F 9 I: C, 34.59; H, 4.15. Found: C, 34.38; H, 4.47.
3)1,1,1,2,2,3,3,4,4,5,5,6,6,7,7−ペンタデカフルオロ−9−ヨードヘプタデカン(27)
無色透明液体。
1H−NMR(400MHz,CDCl3)δ4.33(1H,tt,J=4.4,8.8Hz),2.88(1H,m),2.77(1H,m),1.80(2H,m),1.36−1.43(12H,m),0.89(3H,t,J=6.4Hz)。
19F−NMR(376MHz,CDCl3)δ−81.4(3F),−111.9−−115.5(2F,dd,J=277.5Hz,1363.8Hz),−122.1(2F),−122.6(2F),−123.3(2F),−124.2(2F),−126.7(2F)。
3) 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-9-iodoheptadecane (27)
Colorless transparent liquid.
1 H-NMR (400 MHz, CDCl 3 ) δ 4.33 (1 H, tt, J=4.4, 8.8 Hz), 2.88 (1 H, m), 2.77 (1 H, m), 1.80. (2H,m), 1.36-1.43 (12H,m), 0.89 (3H,t, J=6.4Hz).
19 F-NMR (376 MHz, CDCl 3 ) δ-81.4 (3F), -111.9--115.5 (2F, dd, J=277.5 Hz, 1363.8 Hz), -122.1 (2F). ), -122.6 (2F), -123.3 (2F), -124.2 (2F), -126.7 (2F).
4)1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8−ヘプタフルオロ−10−ヨードオクタデカン(28)
無色透明液体。
1H−NMR(400MHz,CDCl3)δ4.33(1H,tt,J=4.4,8.8Hz),2.88(1H,m),2.77(1H,m),1.80(2H,m),1.36−1.43(12H,m),0.89(3H,t,J=6.4Hz)。
19F−NMR(376MHz,CDCl3)δ−81.5(3F),−111.9−−115.5(2F,dd,J=277.5Hz,1363.8Hz),−122.4(6F),−123.3(2F),−124.1(2F),−126.7(2F)。
4) 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptafluoro-10-iodooctadecane (28)
Colorless transparent liquid.
1 H-NMR (400 MHz, CDCl 3 ) δ 4.33 (1 H, tt, J=4.4, 8.8 Hz), 2.88 (1 H, m), 2.77 (1 H, m), 1.80. (2H,m), 1.36-1.43 (12H,m), 0.89 (3H,t, J=6.4Hz).
19 F-NMR (376 MHz, CDCl 3 ) δ-81.5 (3F), -111.9--115.5 (2F, dd, J=277.5 Hz, 1363.8 Hz), -122.4 (6F). ), -123.3 (2F), -124.1 (2F), -126.7 (2F).
本発明により、簡便にパーフルオロアルキルラジカル類を反応種として用いた含フッ素化合物の製造が可能となった。本発明の方法で得られる含フッ素化合物は各種、医農薬、電子材料の合成原料として利用可能である。 According to the present invention, it becomes possible to easily produce a fluorine-containing compound using perfluoroalkyl radicals as a reaction seed. The fluorine-containing compound obtained by the method of the present invention can be used as a raw material for the synthesis of various medicines, agricultural chemicals and electronic materials.
Claims (4)
下記一般式(2)
又は、
下記一般式(3)
下記一般式(4)
R8−I (4)
(式(4)中、R8は、トリフルオロメチル基、ペンタフルオロエチル基、炭素数3〜8の直鎖若しくは分岐若しくは環式のパーフルオロアルキル基、メトキシカルボニルジフルオロメチル基又はエトキシカルボニルジフルオロメチル基を示す)で表される含フッ素有機ヨウ素化合物とを、
光照射下、反応させることを特徴とする、
下記一般式(5)
又は、
下記一般式(6)
で表わされる含フッ素化合物の製造方法。 The following general formula (1)
The following general formula (2)
Or
The following general formula (3)
The following general formula (4)
R 8 -I (4)
(In the formula (4), R 8 is a trifluoromethyl group, a pentafluoroethyl group, a linear or branched or cyclic perfluoroalkyl group having 3 to 8 carbon atoms, a methoxycarbonyldifluoromethyl group or an ethoxycarbonyldifluoromethyl group. And a fluorine-containing organic iodine compound represented by
Characterized by reacting under light irradiation,
The following general formula (5)
Or
The following general formula (6)
A method for producing a fluorine-containing compound represented by.
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JP2004256406A (en) * | 2003-02-25 | 2004-09-16 | Daikin Ind Ltd | Method for producing fluorine-containing alkylethyl halide and fluorine-containing alkane |
JP2017052734A (en) * | 2015-09-11 | 2017-03-16 | 国立大学法人お茶の水女子大学 | Production method of fluorine-containing compound |
JP2017128525A (en) * | 2016-01-19 | 2017-07-27 | 国立大学法人お茶の水女子大学 | Method for producing fluorine-containing compound |
JP2018043940A (en) * | 2016-09-13 | 2018-03-22 | 国立大学法人お茶の水女子大学 | Method for producing fluorine-containing compound |
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JPH11279087A (en) * | 1998-03-26 | 1999-10-12 | Osaka Gas Co Ltd | Production of fluoroalkyl group-containing compound and addtion reaction catalyst |
JP2001233806A (en) * | 2000-02-28 | 2001-08-28 | Daikin Ind Ltd | Perfluoroalkyl group-containing compound and method for producing the same |
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