JP2019531266A - 1−ヒドロキシメチル−1,2,2,6−テトラメチル−シクロヘキサン及びその誘導体、並びにそれらのアロマケミカルとしての使用 - Google Patents
1−ヒドロキシメチル−1,2,2,6−テトラメチル−シクロヘキサン及びその誘導体、並びにそれらのアロマケミカルとしての使用 Download PDFInfo
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- JP2019531266A JP2019531266A JP2019505384A JP2019505384A JP2019531266A JP 2019531266 A JP2019531266 A JP 2019531266A JP 2019505384 A JP2019505384 A JP 2019505384A JP 2019505384 A JP2019505384 A JP 2019505384A JP 2019531266 A JP2019531266 A JP 2019531266A
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- Prior art keywords
- compound
- formula
- alkyl
- compounds
- alkenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000126 substance Substances 0.000 title claims abstract description 50
- YYYKKHQLNRYFLS-UHFFFAOYSA-N (1,2,2,6-tetramethylcyclohexyl)methanol Chemical compound CC1C(C)(CO)C(C)(C)CCC1 YYYKKHQLNRYFLS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 247
- 238000000034 method Methods 0.000 claims abstract description 46
- 150000002148 esters Chemical class 0.000 claims abstract description 25
- 150000002576 ketones Chemical class 0.000 claims abstract description 19
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 11
- -1 Compound ketone Chemical class 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 239000003205 fragrance Substances 0.000 claims description 33
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 27
- 239000000796 flavoring agent Substances 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 19
- 235000019634 flavors Nutrition 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000002304 perfume Substances 0.000 claims description 15
- 239000003599 detergent Substances 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 230000002708 enhancing effect Effects 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 239000012038 nucleophile Substances 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- 239000002537 cosmetic Substances 0.000 claims description 7
- 239000003446 ligand Substances 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 6
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 claims description 5
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 229960005233 cineole Drugs 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- 238000006640 acetylation reaction Methods 0.000 claims description 4
- 238000005882 aldol condensation reaction Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 241000218645 Cedrus Species 0.000 claims description 3
- 241000597000 Freesia Species 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 235000009508 confectionery Nutrition 0.000 claims description 3
- 235000011869 dried fruits Nutrition 0.000 claims description 3
- 230000001953 sensory effect Effects 0.000 claims description 3
- 239000010902 straw Substances 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 241000212322 Levisticum officinale Species 0.000 claims 1
- 239000001645 levisticum officinale Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 150000003839 salts Chemical class 0.000 description 27
- 239000003795 chemical substances by application Substances 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- 150000002431 hydrogen Chemical class 0.000 description 22
- 239000006210 lotion Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000006071 cream Substances 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 13
- 238000007254 oxidation reaction Methods 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 125000006017 1-propenyl group Chemical group 0.000 description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000002781 deodorant agent Substances 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241000207199 Citrus Species 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 235000020971 citrus fruits Nutrition 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical group [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- NEHNMFOYXAPHSD-JTQLQIEISA-N (S)-(-)-Citronellal Chemical compound O=CC[C@@H](C)CCC=C(C)C NEHNMFOYXAPHSD-JTQLQIEISA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 5
- 239000000645 desinfectant Substances 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 235000013355 food flavoring agent Nutrition 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 4
- 0 CC(*)C1(C)C(C)(*)CCCC1C Chemical compound CC(*)C1(C)C(C)(*)CCCC1C 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003213 antiperspirant Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 150000002366 halogen compounds Chemical class 0.000 description 4
- 150000002561 ketenes Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 150000002902 organometallic compounds Chemical class 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- NEHNMFOYXAPHSD-SNVBAGLBSA-N (+)-Citronellal Chemical compound O=CC[C@H](C)CCC=C(C)C NEHNMFOYXAPHSD-SNVBAGLBSA-N 0.000 description 3
- NYFWXNHQGIXEKH-UHFFFAOYSA-N CC1C2(C)C=[O](C)C2(C)CCC1 Chemical compound CC1C2(C)C=[O](C)C2(C)CCC1 NYFWXNHQGIXEKH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000001166 anti-perspirative effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000007844 bleaching agent Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000009499 grossing Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- 238000007493 shaping process Methods 0.000 description 3
- 239000000516 sunscreening agent Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- FAGYGFPZNTYLAO-JTQLQIEISA-N (3s)-3,7-dimethyl-2-methylideneoct-6-enal Chemical compound O=CC(=C)[C@@H](C)CCC=C(C)C FAGYGFPZNTYLAO-JTQLQIEISA-N 0.000 description 2
- 235000012121 (S)-(-)-citronellal Nutrition 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000723346 Cinnamomum camphora Species 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229910019093 NaOCl Inorganic materials 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 241000218657 Picea Species 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000002386 air freshener Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- HORIEOQXBKUKGQ-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCC(C)C HORIEOQXBKUKGQ-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 229930003633 citronellal Natural products 0.000 description 2
- 235000000983 citronellal Nutrition 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
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- 239000011248 coating agent Substances 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 2
- 239000008271 cosmetic emulsion Substances 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003974 emollient agent Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 235000012438 extruded product Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
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- 239000002917 insecticide Substances 0.000 description 2
- 229930002839 ionone Natural products 0.000 description 2
- 150000002499 ionone derivatives Chemical class 0.000 description 2
- 239000002973 irritant agent Substances 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 150000004715 keto acids Chemical class 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
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- 230000003020 moisturizing effect Effects 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 125000005430 oxychloro group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000012437 perfumed product Substances 0.000 description 2
- 239000001024 permanent hair color Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
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- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- DAFQZPUISLXFBF-UHFFFAOYSA-N tetraoxathiolane 5,5-dioxide Chemical compound O=S1(=O)OOOO1 DAFQZPUISLXFBF-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229910000045 transition metal hydride Chemical class 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- AGFGXVAAIXIOFZ-UHFFFAOYSA-L zinc;butanedioate Chemical compound [Zn+2].[O-]C(=O)CCC([O-])=O AGFGXVAAIXIOFZ-UHFFFAOYSA-L 0.000 description 1
- WDHVIZKSFZNHJB-UHFFFAOYSA-L zinc;butanoate Chemical compound [Zn+2].CCCC([O-])=O.CCCC([O-])=O WDHVIZKSFZNHJB-UHFFFAOYSA-L 0.000 description 1
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1
- XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 description 1
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Abstract
Description
式(A)の化合物のエステル、
及び式(A)の化合物のケトンを提供する。ただし、化合物(A)が式(A)のエステルである場合にはR1はまた水素であってもよい。
R2はC1〜C5アルキルから選択される。]
から選択される。
から選択される。
を製造するための方法であって、
i)式(D)の化合物
iia)式(D)の化合物を、ヒドリド化合物から選択される還元剤と反応させ、又は触媒的水素化により反応させ、式(A.a)の化合物
iib)式(D)の化合物を、少なくとも1つのリガンドR3[ここで、R3はC1〜C8アルキル、及びC2〜C8アルケニルから選択される。]を含む有機金属化合物から選択される求核剤と反応させ、式(A.b)の化合物
を含む方法を提供する。
a)本明細書で定義される式(A)の化合物、式(A)の化合物のエステル、及び式(A)の化合物のケトンから選択される少なくとも1種の化合物、
b)任意で、成分a)の化合物と異なる少なくとも1種の別のアロマケミカル、及び
c)任意で、少なくとも1種の希釈剤
を含む着香味料組成物に関する。ただし、当該組成物は少なくとも1種の成分b)又はc)を含む。
官能的に(organoleptically)有効な量の、本明細書で定義される式(A)の化合物、式(A)の化合物のエステル、及び式(A)の化合物のケトンから選択される少なくとも1種の化合物を含み、かつ/又は
官能的に有効な量の、本明細書で定義される少なくとも1種の着香味料組成物を含む、
香気付けられた(perfumed)又は芳香付けられた(aromatized)製品に関する。
−本化合物は有利な芳香特性を示す。
−本化合物は単純な反応で大量に得ることができる。
−本化合物は効果的な合成経路を介して容易に入手できる。
−第4級炭素原子に近接するメチル基の導入
−本合成経路により合成の際精製工程無しで合成することが可能となり、それにより当該経路を容易に拡大(upscaling)/短縮化すること(telescoping)が可能となる。
本発明は、R1が水素、C1〜C8アルキル、及びC2〜C8アルケニルから選択される、本明細書で定義される式(A)の化合物に関する。
本発明はまた、式(A)の化合物のエステルに関し、
R1は水素、C1〜C8アルキル、及びC2〜C8アルケニルから選択され、
R2はC1〜C5アルキルから選択される。
を用いて行われる。好ましくは、RK1及びRK2は互いに独立に水素、C1〜C8アルキル、及びC2〜C8アルケニルから選択され、それらはより好ましくは同一である。
式中、R1は水素、C1〜C8アルキル、及びC2〜C8アルケニルから選択され、
R2はC1〜C5アルキルから選択される。
R2はC1〜C3アルキル、特にメチル及びエチルから選択される。より好ましくは、R1は水素であり、R2はC1〜C3アルキル、特にメチル及びエチルから選択される。
本発明はまた、式(A)の化合物のケトン
−好ましくは(2,2,6,6-テトラメチルピペリジン-1-イル)-オキシダニル(TEMPO)の使用と共に、N−オキシドを触媒として用い、塩素化溶媒中で次亜塩素酸ナトリウム(NaOCl)を用いた酸化;
−Mo、W、Mn若しくはV触媒を用い、水において又は水と適切な有機溶媒との混合物において、H2O2水を用いた酸化;
−白金及びO2、具体的にはPtO2及びO2、並びに/又はPt/C及びO2を用いた酸化。一般的な方法は例えば、Heyns, Blazejewicz in Tetrahedron, 1960, 9, 67-75により記載されている。
本発明はまた、式(A)の化合物を合成するための方法であって、
i)本明細書に定義される式(D)の化合物
iia)式(D)の化合物を、ヒドリド化合物から選択される還元剤と反応させ、又は触媒的水素化により反応させ、式(A.a)の化合物を得ること、若しくは
iib)式(D)の化合物を、少なくとも1つのリガンドR3[ここで、R3はC1〜C8アルキル及びC2〜C8アルケニルから選択される。]を含む有機金属化合物から選択される求核剤と反応させ、式(A.b)の化合物を得ること
を含む方法を提供する。
i)式(D)の化合物を提供すること、及び
iia)式(D)の化合物を、ヒドリド化合物から選択される還元剤と反応させ、又は触媒的水素化により反応させ、式(A.a)の化合物を得ること
を含む方法を提供する。
a 銅クロマイト(Cu/Cr)を触媒として用いる、特開平04−283527号公報に類似の方法。
b Synlett 2000, 4, 197-200、特に前記論文の化合物8aの8bへの反応、に類似の方法。
c 100bar以下のH2と共に、150℃以下で、数時間THF中で、ZrO2上のRu(10重量%)を触媒として用いる方法。
d 10bar以下のH2と共に、60℃以下で数時間、任意でMe3N(5重量%)を含有するMeOH中で、Pd/Cを触媒として用いる方法。
e 30bar以下のH2と共に、60℃以下で数時間、任意でMe3N(0.1〜1重量%)を含有するMeOH中で、任意でFeを含有するRu/Cを触媒として用いる方法。
iiia)式(A.a)の化合物を、ケテン、飽和及び不飽和モノカルボン酸、並びにそれらのハロゲン化物、無水物、及びC1〜C4アルキルエステルから選択される化合物と反応させて、式(B.a)の化合物(式中、R2は本明細書で定義される通りである。)を得ること
を更に含む。
i)式(D)の化合物を提供すること、
iia)式(D)の化合物を、ヒドリド化合物から選択される還元剤と反応させ、式(A.a)の化合物を得ること、及び
iiia)式(A.a)の化合物を、ケテン、飽和及び不飽和モノカルボン酸、並びにそれらのハロゲン化物、無水物、及びC1〜C4アルキルエステルから選択される化合物と反応させて、式(B.a)の化合物を得ること
を含み、R2は本明細書で定義される通りである、方法を提供する。
i)式(D)の化合物を提供すること、及び
iib)式(D)の化合物を、少なくとも1つのリガンドR3を含む有機金属化合物から選択される求核剤と反応させ、式(A.b)の化合物を得ること
を含み、R3が本明細書に記載の通りである、方法を提供する。
iiib)式(A.b)の化合物を酸化試薬と反応させて式(C)の化合物を得ること[ここで、R3は本明細書に定義される通りである。]
をさらに含む。
i)式(D)の化合物を提供すること、
iib)式(D)の化合物を、少なくとも1つのリガンドR3を含む有機金属化合物から選択される求核剤と反応させ、式(A.b)の化合物を得ること、及び
iiib)式(A.b)の化合物を酸化試薬と反応させて式(C)の化合物を得ること
を含み、R3は本明細書に定義される通りである、方法を提供する。
−次亜塩素酸ナトリウム(NaOCl)を用いた酸化;
−Mo、W、Mn若しくはV触媒を用い、水中で又は水と適切な有機溶媒との混合物中で、H2O2水を用いた酸化;
−白金及びO2、具体的にはPtO2及びO2、並びに/又はPt/C及びO2を用いた酸化である。
本発明は、式(A)の化合物を合成するための方法であって、
ia)式(D.a)の化合物
ib)式(D.a)の化合物をアルドール縮合反応に付し、式(D.b)の化合物
ic)式(D.b)の化合物を水素化反応に付し、式(D.c)の化合物
id)式(D.c)の化合物をアセチル化反応に付し、式(D.d)の化合物
ie)式(D.d)の化合物を環化反応に付し、式(D)の化合物を得ること
を含む方法をさらに提供する。
本発明はさらに、本明細書に定義される式(A)、(B)、(C)及び(D)、好ましくは(A)、(B)及び(C)の化合物をアロマケミカルとして提供する。アロマケミカルとして使用される好ましい化合物は、本明細書に記載の化合物、特に式(A.1)、(A.2)、(A.3)、(A.4)、(A.5)、(B.1)、(B.2)、(C.1)、(C.2)、(C.3)及び(C.4)、特に(A.1)、(A.2)、(A.3)、(A.4)、(A.5)、(B.1)、(C.1)、(C.2)及び(C.3)の化合物から選択される化合物である。特に好ましい化合物は、(A.1)、(A.2)、(A.3)、(B.1)、(C.1)、(C.2)及び(C.3)である。
本発明は、
a)式(A)、(B)、(C)及び(D)の化合物から選択される、好ましくは式(A)、(B)及び(C)の化合物から選択される少なくとも1種の化合物、
b)任意で、成分a)の化合物と異なる少なくとも1種の別のアロマケミカル、及び
c)任意で、少なくとも1種の希釈剤
を含む着香味料組成物(ただし当該組成物は少なくとも1種の成分b)又は成分c)を含む。)をさらに提供する。
本発明は、
−官能的に有効な量の、本明細書に定義される式(A)、(B)、(C)及び(D)の化合物から選択される、好ましくは式(A)、(B)及び(C)の化合物から選択される少なくとも1種の化合物を含み、かつ/又は
−官能的に有効な量の、本明細書に定義される少なくとも1種の着香味料組成物を含む、
香気付けられた又は芳香付けられた製品をさらに提供する。
−香水エキス、オードパルファム、オードトワレ、オーデコロン、オードソリッド(Eau de Solide)、エクストレパルファム、液体形態、ゲル状形態又は固体担体に適用される形態のエアフレッシュナー、エアロゾールスプレー、香料入りのクリーナー及びオイルから選択される香水製品;
−アフターシェーブ、プレシェーブ製品、スプラッシュコロン、固形及び液体石鹸、シャワー用ゲル、シャンプー、シェービングソープ、シェービングフォーム、バスオイル、例えばスキンクリーム及びローション、フェイスクリーム及びローション、日焼け止めクリーム及びローション、アフターサンクリーム及びローション、ハンドクリーム及びローション、フットクリーム及びローション、除毛クリーム及びローション、アフターシェーブクリーム及びローション、タンニングクリーム及びローション等の水中油型の、油中水型の、及び水中油中水型の化粧用エマルジョン、例えば、ヘアスプレー、ヘアジェル、ヘアセッティングローション、ヘアコンディショナー、ヘアシャンプー、永久及び半永久染毛剤等のヘアケア製品、例えばコールドウェーブ及びヘアスムージング組成物、ヘアトニック、ヘアクリーム及びヘアローション等のヘアシェーピング組成物、例えば脇下スプレー、ロールオン、デオドラントスティック、デオドラントクリーム等のデオドラント及び制汗剤、例えばアイシャドー、マニキュア液、メイクアップ用化粧品、口紅、マスカラ等の装飾的化粧品、歯磨き粉、デンタルフロスから選択されるボディケア製品;
−キャンドル、ランプオイル、線香、殺虫剤、防虫剤、噴射剤、錆除去剤、香気付けられたフレッシュニングワイプ、脇下パッド、乳児用おむつ、生理用ナプキン、トイレットペーパー、化粧用ワイプ、ポケットティッシュ、食洗機脱臭剤から選択される衛生用品;
−例えば床クリーナー、窓クリーナー、食器用洗剤、バス及びサニタリークリーナー、スカーリングミルク(scouring milk)、固形及び液体のトイレクリーナー、粉末及び泡のカーペットクリーナー等の香気付けられた酸性、アルカリ性及び中性クリーナー、例えば家具用艶出し剤、床ワックス、靴クリーム等のワックス及び艶出し剤、消毒剤、表面消毒剤及びサニタリークリーナー、ブレーキクリーナー、パイプクリーナー、水垢除去剤、グリル及びオーブンクリーナー、藻及び苔除去剤、カビ除去剤、ファサードクリーナーから選択される固体表面用クリーナー;
−液体洗剤、粉末洗剤、例えば漂白剤、浸漬剤、しみ除去剤等の洗濯前処理剤、柔軟剤、洗濯石鹸、洗濯タブレットから選択される繊維製品用洗剤。
−特に全用途のクリーナー、床クリーナー、窓クリーナー、食器用洗剤、バス及びサニタリークリーナー、スカーリングミルク、固形及び液体のトイレクリーナー、粉末及び泡のカーペットクリーナーから選択される酸性、アルカリ性又は中性クリーナー、液体洗剤、粉末洗剤、例えば漂白剤、浸漬剤、しみ除去剤等の洗濯前処理剤、柔軟剤、洗濯石鹸、洗濯タブレット、消毒剤、表面消毒剤、
−液体形態、ゲル状形態若しくは固体担体に適用される形態の、又はエアロゾールスプレーとしてのエアフレッシュナー、
−特に家具用艶出し剤、床ワックス、靴クリームから選択されるワックス又は艶出し剤、又は
−特にシャワー用ゲル及びシャンプー、シェービングソープ、シェービングフォーム、バスオイル、例えばスキンクリーム及びローション、フェイスクリーム及びローション、日焼け止めクリーム及びローション、アフターサンクリーム及びローション、ハンドクリーム及びローション、フットクリーム及びローション、除毛クリーム及びローション、アフターシェーブクリーム及びローション、タンニングクリーム及びローション等の水中油型の、油中水型の、及び水中油中水型の化粧用エマルジョン、例えば、ヘアスプレー、ヘアジェル、ヘアセッティングローション、ヘアコンディショナー、永久及び半永久染毛剤等のヘアケア製品、例えばコールドウェーブ及びヘアスムージング組成物、ヘアトニック、ヘアクリーム及びヘアローション等のヘアシェーピング組成物、例えば脇下スプレー、ロールオン、デオドラントスティック、デオドラントクリーム等のデオドラント及び制汗剤、装飾的化粧品の製品から選択されるボディケア組成物。
保存剤、研磨剤、抗ニキビ剤、皮膚老化に対抗するための薬剤、抗菌剤、抗脂肪沈着剤、ふけ防止剤、抗炎症剤、刺激防止剤、刺激緩和剤、抗微生物剤、抗酸化剤、収斂剤、発汗抑制剤、防腐剤、帯電防止剤、結合剤、緩衝剤、担体材料、キレート剤、細胞賦活剤、洗浄剤、ケア剤、除毛剤、界面活性物質、脱臭剤、制汗剤、皮膚軟化剤、乳化剤、酵素、精油、繊維、膜形成剤、固定剤、泡形成剤、泡安定剤、発泡防止用物質、泡増幅剤、殺菌剤、ゲル化剤、ゲル形成剤、ヘアケア剤、ヘアシェーピング剤、ヘアスムージング剤、水分供与剤、保湿物質、湿潤物質、漂白剤、補強材、しみ除去剤、蛍光増白剤、含浸剤、防汚剤、摩擦低減剤、潤滑剤、保湿クリーム、軟膏、乳白剤、可塑剤、被覆剤、艶出し剤、光沢剤、ポリマー、粉末、タンパク質、加脂剤、皮膚剥離剤、シリコーン、皮膚鎮静剤、スキンクレンジング剤、スキンケア剤、皮膚治癒剤、皮膚美白剤、皮膚保護剤、皮膚軟化剤、冷却剤、皮膚冷却剤、加温剤、皮膚加温剤、安定剤、UV吸収剤、UV除去剤、洗剤、柔軟剤、懸濁化剤、皮膚タンニング剤、増粘剤、ビタミン、オイル、ワックス、脂肪、リン脂質、飽和脂肪酸、モノ又はポリ不飽和脂肪酸、α−ヒドロキシ酸、ポリヒドロキシ脂肪酸、液化剤、染料、色保護剤、顔料、防食剤、芳香物質、香味料、着香剤、ポリオール、界面活性剤、電解質、有機溶媒又はシリコーン誘導体。
化合物の香りは、匂い紙上の試料の匂いを感じること(smelling)又は嗅ぐこと(sniffing)により判定した。数字が示されている場合、それは、(1)=非常に弱い〜(6)=非常に強い、の範囲の強度を表示する。
1H-NMR (500 MHz, CDCl3): δ= 9.5 (s, 1 H), 6.3 (s, 1 H), 6.0 (s, 1 H), 5.07 - 5.03 (m, 1 H), 2.71 - 2.64 (m, 1 H), 1.96 - 1.84 (m, 2 H), 1.64 (s, 3 H), 1.54 (s, 3 H), 1.54 - 1.47 (m, 1 H), 1.39 - 1.32 (m, 1 H), 1.04 (d, J = 7.0 Hz, 3 H) ppm.
13C-NMR (125 MHz, CDCl3): δ= 17.5, 19.4, 25.6, 25.7, 30.8, 35.5, 124.0, 131.4, 132.9, 155.3, 194.4 ppm.
香り:シトラス。
1H-NMR (500 MHz, CDCl3, 異性体の混合物): δ= 9.67 (d, J = 1.9 Hz, 1 H), 9.65 (d, J = 1.4 Hz, 1 H), 5.12 - 5.06 (m, 2 H), 2.38 - 2.27 (m, 2 H), 2.09 - 1.90 (m, 6 H), 1.69 - 1.68 (br dd, J = 1.1, 4.7 Hz, 6 H), 1.60 (d, J = 4.7 Hz, 6 H), 1.44 - 1.18 (m, 4 H), 1.04 (d, J = 7.0 Hz, 3 H), 1.00 (d, J = 2.9 Hz, 3 H), 0.99 (d, J = 2.8 Hz, 3 H), 0.84 (d, J = 6.9 Hz, 3 H) ppm.
13C-NMR (125 MHz, CDCl3, 異性体 1): δ= 7.9, 15.2, 17.4, 25.60, 25.64, 32.0, 34.7, 50.4, 123.9, 131.6, 205.35 ppm.
13C-NMR (125 MHz, CDCl3, 異性体 2): δ= 9.7, 17.2, 17.5, 25.56, 25.59, 33.1, 33.2, 51.4, 124.0, 131.6, 205.44 ppm.
香り:ローズ様(部屋全体に広がる)、シトラス、ワックス様。
1H-NMR (500 MHz, CDCl3, 異性体の混合物): δ= 6.96 - 6.94 (m, 1 H), 6.86 - 6.84 (m, 1 H), 5.12 - 5.06 (m, 2 H), 2.13 (s, 3 H), 2.11 (s, 3 H), 1.88 (br q, J = 7.4 Hz, 2 H), 1.67 (br d, J = 1.0 Hz, 6 H), 1.60 (d, J = 1.5 Hz, 3 H), 1.58 (br s, 6 H), 1.53 (d, J = 1.6 Hz, 3 H), 1.44 - 1.27 (m, 8 H), 1.01 (d, J = 6.9 Hz, 3 H), 0.98 (d, J = 6.9 Hz, 3 H) ppm.
E-酢酸エノール: 13C-NMR (125 MHz, CDCl3): δ= 9.6, 17.7, 19.6, 20.8, 25.7, 26.0, 34.7, 36.9, 125.4, 130.1, 131.4, 124.4, 168.2 ppm.
Z-酢酸エノール: 13C-NMR (125 MHz, CDCl3): δ= 12.7, 17.6, 18.6, 20.8, 25.7, 26.1, 31.5, 34.4, 124.6, 125.5, 129.5, 131.3, 168.2 ppm.
1H-NMR (500 MHz, CDCl3): δ= 9.61 (s, 1 H), 2.35 (dqd, J = 13.5, 6.8, 3.6 Hz, 1 H), 1.60 - 1.46 (m, 4 H), 1.18 - 1.10 (m, 2 H), 1.12 (s, 3 H), 0.94 (s, 3 H), 0.83 (s, 3 H), 0.73 (d, J = 6.8 Hz, 3 H).
13C-NMR (125 MHz, CDCl3): δ= 8.2, 17.9, 21.7, 22.8, 27.1, 29.3, 30.6, 36.5, 36.8, 54.2, 209.7 ppm.
香り:ユーカリプトール、カンファー(4)、シトラス(2)、スプルースニードル(2)。
1H-NMR (500 MHz, CDCl3): δ= 3.65 (d, J = 11.8 Hz, 1 H), 3.43 (d, J = 11.8 Hz, 1 H), 1.93 (dtd, J = 13.4, 6.7, 3.7 Hz, 1 H), 1.57 - 1.38 (m, 4 H), 1.28 - 1.16 (m, 2 H), 1.03 (s, 3 H), 0.88 (s, 3 H), 0.86 (d, J = 6.8 Hz, 3 H), 0.71 (s, 3 H) ppm.
13C-NMR (125 MHz, CDCl3): δ= 11.9, 17.1, 22.3, 23.8, 26.8, 31.1, 31.6, 36.1, 38.6, 42.1, 67.2 ppm.
香り:ユーカリプトール(2)、フラワリー(2)、アース様(2)。
1H-NMR (500 MHz, CDCl3): δ= 4.02 (d, J = 11.8 Hz, 1 H), 3.89 (d, J = 11.8 Hz, 1 H), 2.05 (s, 3 H), 1.94 (dtd, J = 13.3, 6.3, 2.6 Hz, 1 H), 1.57 - 1.36 (m, 4 H), 1.25 - 1.16 (m, 1 H), 1.12 - 1.06 (m, 1 H), 0.97 (s, 3 H), 0.88 (s, 3 H), 0.80 (d, J = 6.7 Hz, 3 H), 0.78 (s, 3 H) ppm.
13C-NMR (125 MHz, CDCl3): δ= 11.8, 16.9, 21.3, 22.2, 23.3, 26.8, 30.9, 32.3, 36.1, 38.3, 41.0, 68.3, 171.3 ppm.
香り:ウッディ(2)、スイートパウダリー(2)、フレッシュ(2)、フリージア(2)。
1H-NMR (500 MHz, CDCl3): δ= 5.90 - 5.79 (m, 1 H), 5.14 (br s, 1 H), 5.13 - 5.09 (m, 1 H), 3.75 (d, J = 11.1 Hz, 1 H), 2.43 - 2.38 (m, 1 H), 2.27 - 2.14 (m, 2 H), 1.59 - 1.42 (m, 4 H), 1.36 - 1.20 (m, 2 H), 1.08 (s, 3 H), 0.91 (d, J = 6.8 Hz, 3 H), 0.86 (s, 3 H), 0.82 (s, 3 H) ppm.
13C-NMR (125 MHz, CDCl3):δ= 137.4, 117.8, 73.3, 44.6, 40.0, 38.7, 37.6, 31.6, 31.0, 27.3, 22.4, 24.3, 18.9, 12.5 ppm.
香り:ウッディ(3)、シダー(3)、オークモス(3)。
1H-NMR (500 MHz, CDCl3): δ= 5.96 (ddt, J = 17.1, 10.2, 6.8 Hz, 1 H), 5.16 - 5.11 (m, 1 H), 5.10 - 5.03 (m, 1 H), 3.24 (d, J = 6.8 Hz, 2 H), 2.49 - 2.42 (m, 1 H), 1.55 - 1.48 (m, 4 H), 1.15 (s, 3 H), 1.12 - 1.07 (m, 2 H), 0.94 (s, 3 H), 0.89 (s, 3 H), 0.68 (d, J = 6.6 Hz, 3 H) ppm.
13C-NMR (125 MHz, CDCl3): δ= 213.7, 132.1, 117.6, 57.3, 46.5, 36.9, 36.1, 31.7, 29.9, 27.5, 24.4, 21.6, 18.7, 10.7 ppm.
香り:わら(3)、干し草、アース様(3)、僅かにウッディ(2)
1H-NMR (300 MHz, CDCl3): δ= 3.71 (d, J = 10.6 Hz, 1 H), 2.15 - 2.08 (m, 1 H), 1.60 - 1.21 (m, 12 H), 1.08 (s, 3 H), 0.91 (t, J = 7.3 Hz, 3 H), 0.87 (d, J = 6.8 Hz, 3 H), 0.85 (s, 3 H), 0.80 (s, 3 H) ppm.
13C-NMR (125 MHz, CDCl3): δ= 75.7, 44.8, 38.8, 37.6, 34.8, 31.6, 31.0, 30.4, 27.3, 24.4, 22.8, 22.5, 18.8, 14.2, 12.7 ppm.
1H-NMR (300 MHz, CDCl3, 1つの異性体): δ= 3.61 (dd, J = 11.1, 2.0 Hz, 1 H), 2.16 - 2.09 (m, 1 H), 1.69 - 1.23 (m, 8 H), 1.08 (s, 3 H), 0.98 (t, J = 7.3 Hz, 3 H), 0.87 (d, J = 6.8 Hz, 3 H), 0.85 (s, 3 H), 0.80 (s, 3 H) ppm.
13C-NMR (125 MHz, CDCl3, 1つの異性体): δ= 77.3, 44.9, 38.7, 37.5, 31.6, 31.0, 27.6, 27.3, 24.4, 22.5, 18.8, 12.5, 12.4 ppm.
香り:アンブラ(1)、ナフタレン。
1H-NMR (300 MHz, CDCl3,1つの異性体):δ= 2.5 (m, 3 H), 1.69 - 1.23 (m, 6 H), 1.08 (s, 3 H), 0.98 (t, J = 7.3 Hz, 3 H), 0.87 (d, J = 6.8 Hz, 3 H), 0.85 (s, 3 H), 0.80 (t, 3 H) ppm.
13C-NMR (125 MHz, CDCl3):δ= 216.4, 57.0, 39.1, 36.0, 35.0, 31.8, 29.9, 27.5, 24.5, 21.6, 18.7, 10.7, 8.2 ppm.
香り:アース様(3)、セダーウッド(3)、パウダリー、ドライ。
1H-NMR (500 MHz, CDCl3): δ= 6.9-6.7 (m, 1 H), 5.5 - 5.4 (d, 1 H), 2.49 - 2.42 (m, 1 H), 1.9-1.8 (d, 3 H), 1.55 - 1.48 (m, 4 H), 1.15 (s, 3 H), 1.12 - 1.07 (m, 2 H), 0.94 (s, 3 H), 0.89 (s, 3 H), 0.68 (d, J = 6.6 Hz, 3 H) ppm.
13C-NMR (125 MHz, CDCl3): δ= 203.9, 140.7, 129.4, 55.7, 37.0, 36.1, 31.5, 30.0, 27.3, 24.3, 21.8, 18.4, 18.3, 10.7 ppm.
香り:ドライフルーツ(3)、ダマスコン(3)、ローズ様(3)、ラビッジ(lovage)(2)。
1H-NMR (500 MHz, CDCl3):δ= 2.47 - 2.36 (m, 3 H), 1.55 - 1.42 (m, 6 H), 1.33 - 1.21 (m, 2 H), 1.12 (s, 3 H), 1.11 - 1.03 (m, 2 H), 0.90 (s, 3 H), 0.89 (t, J = 7.3 Hz, 3 H), 0.86 (s, 3 H), 0.63 (d, J = 6.6 Hz, 3 H) ppm.
13C-NMR (125 MHz, CDCl3): δ= 215.9, 56.9, 41.8, 37.0, 36.0, 31.8, 29.9, 27.6, 26.2, 24.5, 22.5, 21.6, 18.7, 14.1, 10.7 ppm.
1H-NMR (500 MHz, CDCl3): δ= 4.00 (d, J = 11.8 Hz, 1 H), 3.89 (d, J = 11.8 Hz, 1 H), 2.31 (q, J = 7.8 Hz, 2 H), 1.98 - 1.90 (m, 1 H), 1.56 - 1.35 (m, 4 H), 1.24 - 1.16 (m, 1 H), 1.13 (t, J = 7.6 Hz, 3 H), 1.09 - 1.07 (m, 1 H), 0.96 (s, 3 H), 0.87 (s, 3 H), 0.79 (d, J = 6.7 Hz, 3 H), 0.76 (s, 3 H) ppm.
13C-NMR (125 MHz, CDCl3): δ= 174.5, 68.1, 41.1, 38.3, 36.1, 32.3, 31.0, 28.0, 26.8, 23.4, 22.3, 16.9, 11.9, 9.2 ppm.
Claims (15)
- 工程iib)において、求核剤が少なくとも1つのリガンドR3を含む金属C1〜C8アルキル化合物及び金属C1〜C8アルケニル化合物から選択される、式(A.b)の化合物を合成するための請求項5に記載の方法。
- 請求項1〜3のいずれか1項に記載の化合物のアロマケミカルとしての使用。
- 官能的に(organoleptically)有効な量の、少なくとも1種の請求項1〜3のいずれか1項に定義される化合物又は請求項11に定義される化合物(D)を含み、及び/又は官能的に有効な量の、請求項11に定義される少なくとも1種の着香味料組成物を含む、香気付けられた(perfumed)又は芳香付けられた(aromatized)製品。
- 前記製品は、好ましくは、香気ディスペンサー及び香料香水、洗剤及びクリーナー、化粧用組成物、ボディケア組成物、衛生用品、口腔及び歯科衛生用製品、香気ディスペンサー、香料、薬学的組成物並びに作物保護組成物から選択される、請求項12に記載の香気付けられた又は芳香付けられた製品。
- 官能的に有効な量の、少なくとも1種の請求項1〜3のいずれか1項に定義される化合物又は請求項11に定義される化合物(D)に製品を接触させる、製品の香り又は風味を付与及び/又は増強するための方法。
- 以下から選択される化合物のアロマケミカルとしての使用:
−ユーカリプトール、フラワリー、アース様(earth-like)の芳香を有する式(A.1)の化合物、
−ウッディ、スイートパウダリー、フレッシュ、フリージアの芳香を有する式(B.1)の化合物、
−ウッディ、シダー、オークモスの芳香を有する式(A.3)の化合物、
−わら、干し草、アース様、僅かにウッディの芳香を有する式(C.1)の化合物、
−アンブラ(ambra)、ナフタレンの芳香を有する式(A.2)の化合物、
−アース様、セダーウッド、パウダリー、ドライの芳香を有する式(C.3)の化合物、
−ドライフルーツ、ダマスコン、ローズ様、ラビッジ(lovage)の芳香を有する式(C.2)の化合物。
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PCT/EP2017/069637 WO2018024820A1 (en) | 2016-08-04 | 2017-08-03 | 1-hydroxymethyl-1,2,2,6-tetramethyl-cyclohexane and derivatives thereof and their use as aroma chemicals |
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CN110431126B (zh) | 2017-03-20 | 2022-12-02 | 巴斯夫欧洲公司 | 制备一溴三氯甲烷的方法 |
BR112019023173A2 (pt) | 2017-05-06 | 2020-06-02 | Basf Se | Composto, composição, método para preparar um composto, uso de um composto ou de uma composição, substância aromática e/ou composição de fragrância, produto perfumado ou com fragrância, e, método para perfumar um produto |
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