NO814333L - Substituerte nonensyrer og derivater derav - Google Patents
Substituerte nonensyrer og derivater deravInfo
- Publication number
- NO814333L NO814333L NO814333A NO814333A NO814333L NO 814333 L NO814333 L NO 814333L NO 814333 A NO814333 A NO 814333A NO 814333 A NO814333 A NO 814333A NO 814333 L NO814333 L NO 814333L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- ether
- hepten
- hydroxy
- formula
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 15
- 150000007513 acids Chemical class 0.000 title description 7
- -1 prenyl halide Chemical class 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000004593 Epoxy Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000011777 magnesium Substances 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 239000003223 protective agent Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000008707 rearrangement Effects 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 22
- 239000002904 solvent Substances 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 9
- 101150041968 CDC13 gene Proteins 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- OINDAOPLJVQNGS-UHFFFAOYSA-N 1-chloro-6-methylhept-5-en-2-ol Chemical compound CC(C)=CCCC(O)CCl OINDAOPLJVQNGS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- BHQJVTVWQXAPCN-UHFFFAOYSA-N 1-bromo-6-methylhept-5-en-2-ol Chemical compound CC(C)=CCCC(O)CBr BHQJVTVWQXAPCN-UHFFFAOYSA-N 0.000 description 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JKXQKGNGJVZKFA-UHFFFAOYSA-N 1-chloro-3-methylbut-2-ene Chemical compound CC(C)=CCCl JKXQKGNGJVZKFA-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- WOPYURXQWMHYFG-UHFFFAOYSA-N 2-[2-(5-hydroxy-4,8-dimethylnon-7-enyl)-2-methyl-3,8-dioxabicyclo[3.2.1]octan-5-yl]acetic acid Chemical compound CC(C)=CCC(O)C(C)CCCC1(C)OCC2(CC(O)=O)CCC1O2 WOPYURXQWMHYFG-UHFFFAOYSA-N 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- NXUVHGREAWBOSP-UHFFFAOYSA-N 9-chloro-8-hydroxy-4-methylnon-4-enoic acid Chemical compound CC(CCC(O)=O)=CCCC(O)CCl NXUVHGREAWBOSP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
- GMVSXZWDCRTQAN-UHFFFAOYSA-N ethyl 6-(1-bromoethyl)-6-[2-(1-bromoethyl)-6-ethoxycarbonyl-5-hept-1-en-2-yloxan-2-yl]oxy-3-hept-1-en-2-yloxane-2-carboxylate Chemical compound O1C(C(=O)OCC)C(C(=C)CCCCC)CCC1(C(C)Br)OC1(C(C)Br)OC(C(=O)OCC)C(C(=C)CCCCC)CC1 GMVSXZWDCRTQAN-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- IFSYJVQRVQMRKN-ONEGZZNKSA-N (E)-hept-5-en-2-ol Chemical compound C\C=C\CCC(C)O IFSYJVQRVQMRKN-ONEGZZNKSA-N 0.000 description 1
- 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- IFMYFXJJIIGOIS-UHFFFAOYSA-N 1-(pyridin-3-ylmethyl)piperidin-4-amine;trihydrochloride Chemical compound Cl.Cl.Cl.C1CC(N)CCN1CC1=CC=CN=C1 IFMYFXJJIIGOIS-UHFFFAOYSA-N 0.000 description 1
- DIFWBLNLJZLDDY-UHFFFAOYSA-N 1-bromo-4-(3,3-dimethyloxiran-2-yl)butan-2-ol Chemical compound CC1(C)OC1CCC(O)CBr DIFWBLNLJZLDDY-UHFFFAOYSA-N 0.000 description 1
- DYTOTUJRYBXIED-UHFFFAOYSA-N 1-bromo-6-methylhept-6-ene-2,5-diol Chemical compound CC(=C)C(O)CCC(O)CBr DYTOTUJRYBXIED-UHFFFAOYSA-N 0.000 description 1
- WSIFORPVHSINQQ-UHFFFAOYSA-N 1-chloro-6-methylhept-6-ene-2,5-diol Chemical compound CC(=C)C(O)CCC(O)CCl WSIFORPVHSINQQ-UHFFFAOYSA-N 0.000 description 1
- LBFTVBIHZPCKME-UHFFFAOYSA-N 1-prop-1-en-2-yloxybutane Chemical compound CCCCOC(C)=C LBFTVBIHZPCKME-UHFFFAOYSA-N 0.000 description 1
- PXSBSBDNZRLRLK-UHFFFAOYSA-N 2-(2h-pyran-2-yloxy)-2h-pyran Chemical compound O1C=CC=CC1OC1OC=CC=C1 PXSBSBDNZRLRLK-UHFFFAOYSA-N 0.000 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical class O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- BTHLKLUTMYTDFM-UHFFFAOYSA-N 2-ethoxyoxane Chemical compound CCOC1CCCCO1 BTHLKLUTMYTDFM-UHFFFAOYSA-N 0.000 description 1
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 1
- LXNRGNULNRZHBK-UHFFFAOYSA-N 3-[4-chloro-6-[3-chloro-6-(3,3-dimethyloxiran-2-yl)-1-methoxyhexoxy]-6-methoxyhexyl]-2,2-dimethyloxirane Chemical compound O1C(C)(C)C1CCCC(Cl)CC(OC)OC(OC)CC(Cl)CCCC1OC1(C)C LXNRGNULNRZHBK-UHFFFAOYSA-N 0.000 description 1
- AJBSJDWDWAUOPL-UHFFFAOYSA-N 6-(bromomethyl)-7-[2-(bromomethyl)-1-methoxy-6-methylhept-5-enoxy]-7-methoxy-2-methylhept-2-ene Chemical compound CC(C)=CCCC(CBr)C(OC)OC(OC)C(CBr)CCC=C(C)C AJBSJDWDWAUOPL-UHFFFAOYSA-N 0.000 description 1
- BFJWJQFJCZKNHG-UHFFFAOYSA-N 6-(bromomethyl)-7-[2-(bromomethyl)-5-hydroxy-1-methoxy-6-methylhept-6-enoxy]-7-methoxy-2-methylhept-1-en-3-ol Chemical compound CC(=C)C(O)CCC(CBr)C(OC)OC(OC)C(CBr)CCC(O)C(C)=C BFJWJQFJCZKNHG-UHFFFAOYSA-N 0.000 description 1
- MGTHTKTULIYHTL-UHFFFAOYSA-N 6-(bromomethyl)-8-[3-(bromomethyl)-1-butoxy-7-methyloct-6-enoxy]-8-butoxy-2-methyloct-2-ene Chemical compound BrCC(CCC=C(C)C)CC(OCCCC)OC(CC(CBr)CCC=C(C)C)OCCCC MGTHTKTULIYHTL-UHFFFAOYSA-N 0.000 description 1
- NTTQHIOCSXVXCY-UHFFFAOYSA-N 6-(bromomethyl)-8-[3-(bromomethyl)-1-ethoxy-7-methyloct-6-enoxy]-8-ethoxy-2-methyloct-2-ene Chemical compound BrCC(CCC=C(C)C)CC(OCC)OC(CC(CBr)CCC=C(C)C)OCC NTTQHIOCSXVXCY-UHFFFAOYSA-N 0.000 description 1
- NZFJWAZLGPQMLO-UHFFFAOYSA-N 6-(bromomethyl)-8-[3-(bromomethyl)-1-methoxy-7-methyloct-6-enoxy]-8-methoxy-2-methyloct-2-ene Chemical compound BrCC(CCC=C(C)C)CC(OC)OC(CC(CBr)CCC=C(C)C)OC NZFJWAZLGPQMLO-UHFFFAOYSA-N 0.000 description 1
- DWMNGMVTPAJVSG-UHFFFAOYSA-N 6-(bromomethyl)-8-[3-(bromomethyl)-2-(2-methoxyethoxy)-7-methyloct-6-enoxy]-7-(2-methoxyethoxy)-2-methyloct-2-ene Chemical compound BrCC(CCC=C(C)C)C(COCC(C(CBr)CCC=C(C)C)OCCOC)OCCOC DWMNGMVTPAJVSG-UHFFFAOYSA-N 0.000 description 1
- MBGWYDAJINDNFP-UHFFFAOYSA-N 6-(bromomethyl)-8-[3-(bromomethyl)-7-methyl-1-(2-methylpropoxy)oct-6-enoxy]-2-methyl-8-(2-methylpropoxy)oct-2-ene Chemical compound BrCC(CCC=C(C)C)CC(OCC(C)C)OC(CC(CBr)CCC=C(C)C)OCC(C)C MBGWYDAJINDNFP-UHFFFAOYSA-N 0.000 description 1
- RAMNLYKBHUQRRR-UHFFFAOYSA-N 6-(chloromethyl)-8-[3-(chloromethyl)-1-ethoxy-7-methyloct-6-enoxy]-8-ethoxy-2-methyloct-2-ene Chemical compound ClCC(CCC=C(C)C)CC(OCC)OC(CC(CCl)CCC=C(C)C)OCC RAMNLYKBHUQRRR-UHFFFAOYSA-N 0.000 description 1
- PMCIMWDKFCFFOJ-UHFFFAOYSA-N 6-(chloromethyl)-8-[3-(chloromethyl)-1-methoxy-7-methyloct-6-enoxy]-8-methoxy-2-methyloct-2-ene Chemical compound ClCC(CCC=C(C)C)CC(OC)OC(CC(CCl)CCC=C(C)C)OC PMCIMWDKFCFFOJ-UHFFFAOYSA-N 0.000 description 1
- PEZOWNTUIHCEND-UHFFFAOYSA-N 6-(chloromethyl)-8-[3-(chloromethyl)-7-methyl-1-(2-methylpropoxy)oct-6-enoxy]-2-methyl-8-(2-methylpropoxy)oct-2-ene Chemical compound ClCC(CCC=C(C)C)CC(OCC(C)C)OC(CC(CCl)CCC=C(C)C)OCC(C)C PEZOWNTUIHCEND-UHFFFAOYSA-N 0.000 description 1
- LKXRYAOHSCZHAV-UHFFFAOYSA-N 6-bromo-6-[(1-bromo-3-hept-1-en-2-yl-2-methylcyclohexa-2,4-dien-1-yl)methoxymethyl]-2-hept-1-en-2-yl-1-methylcyclohexa-1,3-diene Chemical compound C1C=CC(C(=C)CCCCC)=C(C)C1(Br)COCC1(Br)C(C)=C(C(=C)CCCCC)C=CC1 LKXRYAOHSCZHAV-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- WBUPCAIROSULDN-UHFFFAOYSA-N 7-bromo-9-(3-bromo-1-butoxy-7-hydroxy-8-methylnon-8-enoxy)-9-butoxy-2-methylnon-1-en-3-ol Chemical compound CC(=C)C(O)CCCC(Br)CC(OCCCC)OC(CC(Br)CCCC(O)C(C)=C)OCCCC WBUPCAIROSULDN-UHFFFAOYSA-N 0.000 description 1
- OROVMVYYXGAVLC-UHFFFAOYSA-N 7-bromo-9-(3-bromo-7-hydroxy-1-methoxy-8-methylnon-8-enoxy)-9-methoxy-2-methylnon-1-en-3-ol Chemical compound CC(=C)C(O)CCCC(Br)CC(OC)OC(CC(Br)CCCC(O)C(C)=C)OC OROVMVYYXGAVLC-UHFFFAOYSA-N 0.000 description 1
- QYTQYVBDABBIDJ-UHFFFAOYSA-N 7-chloro-9-(3-chloro-7-hydroxy-1-methoxy-8-methylnon-8-enoxy)-9-methoxy-2-methylnon-1-en-3-ol Chemical compound ClC(CCCC(C(C)=C)O)CC(OC)OC(CC(CCCC(C(C)=C)O)Cl)OC QYTQYVBDABBIDJ-UHFFFAOYSA-N 0.000 description 1
- FWFBKJXTXHRXIT-UHFFFAOYSA-N 8-butoxy-8-[1-butoxy-3-(chloromethyl)-7-methyloct-6-enoxy]-6-(chloromethyl)-2-methyloct-2-ene Chemical compound ClCC(CCC=C(C)C)CC(OCCCC)OC(CC(CCl)CCC=C(C)C)OCCCC FWFBKJXTXHRXIT-UHFFFAOYSA-N 0.000 description 1
- PYFLBXZJOJKJER-UHFFFAOYSA-N 9-(7-hydroxy-3-iodo-1-methoxy-8-methylnon-8-enoxy)-7-iodo-9-methoxy-2-methylnon-1-en-3-ol Chemical compound CC(=C)C(O)CCCC(I)CC(OC)OC(CC(I)CCCC(O)C(C)=C)OC PYFLBXZJOJKJER-UHFFFAOYSA-N 0.000 description 1
- FZEIEHYJASFSMJ-UHFFFAOYSA-N 9-bromo-8-hydroxy-4-methylnon-4-enoic acid Chemical compound CC(CCC(O)=O)=CCCC(O)CBr FZEIEHYJASFSMJ-UHFFFAOYSA-N 0.000 description 1
- YZEXUISQUBXJRK-UHFFFAOYSA-N 9-butoxy-9-(1-butoxy-3-chloro-7-hydroxy-8-methylnon-8-enoxy)-7-chloro-2-methylnon-1-en-3-ol Chemical compound ClC(CCCC(C(C)=C)O)CC(OCCCC)OC(CC(CCCC(C(C)=C)O)Cl)OCCCC YZEXUISQUBXJRK-UHFFFAOYSA-N 0.000 description 1
- JDKIXGMWXWLKAG-UHFFFAOYSA-N BrC(CCCC1C(C)(C)O1)CC(OC)OC(CC(CCCC1C(C)(O1)C)Br)OC Chemical compound BrC(CCCC1C(C)(C)O1)CC(OC)OC(CC(CCCC1C(C)(O1)C)Br)OC JDKIXGMWXWLKAG-UHFFFAOYSA-N 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- QBYIEDZWJODGBO-UHFFFAOYSA-N ClCC(CCCC(C)C)C1(OC2C(CC1)O2)OC1(OC2C(CC1)O2)C(CCl)CCCC(C)C Chemical compound ClCC(CCCC(C)C)C1(OC2C(CC1)O2)OC1(OC2C(CC1)O2)C(CCl)CCCC(C)C QBYIEDZWJODGBO-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
- 229910007161 Si(CH3)3 Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- JSBYYYCFFSTIDN-UHFFFAOYSA-N [2-(chloromethyl)-6-methylhept-5-enyl]-[[2-(chloromethyl)-6-methylhept-5-enyl]-dimethylsilyl]oxy-dimethylsilane Chemical compound CC(C)=CCCC(CCl)C[Si](C)(C)O[Si](C)(C)CC(CCl)CCC=C(C)C JSBYYYCFFSTIDN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 238000010961 commercial manufacture process Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- UJYVYWFLKPWXFH-UHFFFAOYSA-N ethyl 10-butoxy-10-[1-butoxy-3-(chloromethyl)-10-ethoxy-7-methyl-10-oxodec-6-enoxy]-8-(chloromethyl)-4-methyldec-4-enoate Chemical compound ClCC(CCC=C(C)CCC(=O)OCC)CC(OCCCC)OC(CC(CCl)CCC=C(C)CCC(=O)OCC)OCCCC UJYVYWFLKPWXFH-UHFFFAOYSA-N 0.000 description 1
- LMCIOUSWXRYDGO-UHFFFAOYSA-N ethyl 3-[6-chloro-6-[[1-chloro-2-(3-ethoxy-3-oxopropyl)-3-hept-1-en-2-ylcyclohexa-2,4-dien-1-yl]methoxymethyl]-2-hept-1-en-2-ylcyclohexa-1,3-dien-1-yl]propanoate Chemical compound C1C=CC(C(=C)CCCCC)=C(CCC(=O)OCC)C1(Cl)COCC1(Cl)C(CCC(=O)OCC)=C(C(=C)CCCCC)C=CC1 LMCIOUSWXRYDGO-UHFFFAOYSA-N 0.000 description 1
- IREBSXUUCIDEAL-UHFFFAOYSA-N ethyl 8-(bromomethyl)-10-[3-(bromomethyl)-1-butoxy-10-ethoxy-7-methyl-10-oxodec-6-enoxy]-10-butoxy-4-methyldec-4-enoate Chemical compound BrCC(CCC=C(C)CCC(=O)OCC)CC(OCCCC)OC(CC(CBr)CCC=C(C)CCC(=O)OCC)OCCCC IREBSXUUCIDEAL-UHFFFAOYSA-N 0.000 description 1
- DDKVXVQSOCQYAB-UHFFFAOYSA-N ethyl 8-(bromomethyl)-10-[3-(bromomethyl)-10-ethoxy-7-methyl-1-(2-methylpropoxy)-10-oxodec-6-enoxy]-4-methyl-10-(2-methylpropoxy)dec-4-enoate Chemical compound BrCC(CCC=C(C)CCC(=O)OCC)CC(OCC(C)C)OC(CC(CBr)CCC=C(C)CCC(=O)OCC)OCC(C)C DDKVXVQSOCQYAB-UHFFFAOYSA-N 0.000 description 1
- RASNOPKBFBISNX-UHFFFAOYSA-N ethyl 8-(chloromethyl)-10-[3-(chloromethyl)-10-ethoxy-1-methoxy-7-methyl-10-oxodec-6-enoxy]-10-methoxy-4-methyldec-4-enoate Chemical compound ClCC(CCC=C(C)CCC(=O)OCC)CC(OC)OC(CC(CCl)CCC=C(C)CCC(=O)OCC)OC RASNOPKBFBISNX-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- XEPBEFCJSFMEPF-UHFFFAOYSA-N methyl 10-butoxy-10-[1-butoxy-3-(chloromethyl)-10-methoxy-7-methyl-10-oxodec-6-enoxy]-8-(chloromethyl)-4-methyldec-4-enoate Chemical compound ClCC(CCC=C(C)CCC(=O)OC)CC(OCCCC)OC(CC(CCl)CCC=C(C)CCC(=O)OC)OCCCC XEPBEFCJSFMEPF-UHFFFAOYSA-N 0.000 description 1
- OKZNFNZPDOSHDV-UHFFFAOYSA-N methyl 8-(bromomethyl)-10-[3-(bromomethyl)-1,10-dimethoxy-7-methyl-10-oxodec-6-enoxy]-10-methoxy-4-methyldec-4-enoate Chemical compound BrCC(CCC=C(C)CCC(=O)OC)CC(OC)OC(CC(CBr)CCC=C(C)CCC(=O)OC)OC OKZNFNZPDOSHDV-UHFFFAOYSA-N 0.000 description 1
- AOXKWIKIZPFXLZ-UHFFFAOYSA-N methyl 8-(chloromethyl)-10-[3-(chloromethyl)-1,10-dimethoxy-7-methyl-10-oxodec-6-enoxy]-10-methoxy-4-methyldec-4-enoate Chemical compound ClCC(CCC=C(C)CCC(=O)OC)CC(OC)OC(CC(CCl)CCC=C(C)CCC(=O)OC)OC AOXKWIKIZPFXLZ-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/42—Halogenated unsaturated alcohols acyclic
- C07C33/423—Halogenated unsaturated alcohols acyclic containing only double bonds as unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
- C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
- C07C43/1745—Unsaturated ethers containing halogen containing six-membered aromatic rings having more than one ether bound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55179403A JPS57102829A (en) | 1980-12-18 | 1980-12-18 | 1-halogeno-6-methyl-5-hepten-2-ol, its derivative, and their preparation |
| JP55179404A JPS57102880A (en) | 1980-12-18 | 1980-12-18 | 1-halogeno-5,6-epoxy-6-methyl-2-heptanol, its derivative and preparation thereof |
| JP55180253A JPS57102838A (en) | 1980-12-19 | 1980-12-19 | 9-halogeno-8-hydroxy-4-methyl-4-nonenoic acid, its derivative and their preparation |
| JP55181697A JPS57106633A (en) | 1980-12-22 | 1980-12-22 | 1-halogeno-5-hydroxy-6-methylene-2-heptanol, its derivative and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO814333L true NO814333L (no) | 1982-06-21 |
Family
ID=27474887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO814333A NO814333L (no) | 1980-12-18 | 1981-12-17 | Substituerte nonensyrer og derivater derav |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0054909A3 (es) |
| AU (1) | AU7792481A (es) |
| DK (1) | DK554681A (es) |
| ES (1) | ES508129A1 (es) |
| FI (1) | FI814008L (es) |
| IL (1) | IL64561A0 (es) |
| NO (1) | NO814333L (es) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1317624A (en) * | 1969-09-22 | 1973-05-23 | Zoecon Corp | Hydroxy alkenoic acids derivatives thereof and their use in the control of insects |
| CH564303A5 (es) * | 1971-01-20 | 1975-07-31 | Hoffmann La Roche |
-
1981
- 1981-11-26 AU AU77924/81A patent/AU7792481A/en not_active Abandoned
- 1981-12-14 FI FI814008A patent/FI814008L/fi not_active Application Discontinuation
- 1981-12-14 DK DK554681A patent/DK554681A/da unknown
- 1981-12-15 IL IL64561A patent/IL64561A0/xx unknown
- 1981-12-16 EP EP81110514A patent/EP0054909A3/en not_active Withdrawn
- 1981-12-17 NO NO814333A patent/NO814333L/no unknown
- 1981-12-18 ES ES508129A patent/ES508129A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI814008L (fi) | 1982-06-19 |
| AU7792481A (en) | 1982-06-24 |
| EP0054909A2 (en) | 1982-06-30 |
| DK554681A (da) | 1982-06-19 |
| IL64561A0 (en) | 1982-03-31 |
| ES508129A1 (es) | 1982-11-01 |
| EP0054909A3 (en) | 1982-09-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Ley et al. | A highly convergent total synthesis of the spiroacetal macrolide (+)-milbemycinβ1 | |
| US6376711B1 (en) | Method for the preparation of aryl ethers | |
| US4851585A (en) | Vitamin E intermediates | |
| NO172846B (no) | Fremgangsmaate for fremstilling av 7,8-dihalogen-3-metyl-2,3-dihydro-2m-benzoksazinderivater og propoksybenzenderivater for utoevelse av fremgangsmaaten. | |
| NO814333L (no) | Substituerte nonensyrer og derivater derav | |
| US4059595A (en) | Process for preparing 3-oxy-4H-pyran-4-one derivatives | |
| GB1568735A (en) | Pregnane derivatives | |
| EP0164698B1 (en) | Process for epimerization at c6 of 3,4,5,6-tetra-hydro-2h-pyran-2-one | |
| KR880001427B1 (ko) | 비시클로헵탄 유도체의 제조방법 | |
| CA2306741A1 (en) | Process for the preparation of (2r, 3s)-3-amino-1,2-oxirane | |
| EP0024095B1 (en) | Total synthesis of (1rs, 4sr, 5rs)-4-(4,8-dimethyl-5-hydroxy-7-nonenyl)-4-methyl-3,8-dioxabicyclo (3.2.1) octane-1-acetic acid and intermediates | |
| US4855481A (en) | Process for the preparation of HMG-CoA reductase inhibitors and intermediate compounds employed therein | |
| EA002547B1 (ru) | Способ селективного эпоксидирования для получения лекарственных соединений | |
| EP0020058B1 (en) | Total synthesis of (1rs, 4sr, 5rs)-4-(4,8-dimethyl-5-hydroxy-7-nonenyl)-4-methyl-3,8-dioxabicyclo (3.2.1) octane-1-acetic acid, and intermediates | |
| Mori et al. | Synthetic microbial chemistry, XXIV. Synthesis of antibiotic 1233A, an inhibitor of cholesterol biosynthesis | |
| US4150039A (en) | 2,2'-Bis(3,4-Epoxy-5-oxotetrahydropyran)ethers | |
| DK143199B (da) | Racemiske eller optisk aktive 2-oxabicyclo (3,3,0) octaner til anvendelse som mellemprodukter ved fremstilling af prostaglandinforbindelser og fremgangsmaade til fremstilling deraf | |
| EP0515142B1 (en) | Optically active epoxides and a process for the production thereof | |
| Takano et al. | Diastereodivergent synthesis of optically active trans-and cis-6-benzyloxymethyl-4-hydroxytetrahydro-2-pyrones via 3-hydroxyalkenyl phenyl sulfides | |
| US4568759A (en) | Preparation of epoxides | |
| US4603213A (en) | Total synthesis of 1RS,4SR,5RS-4-(4,8-dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-acetic acid | |
| US4985571A (en) | 6-membered lactones useful as intermediates for antilipemic mevalonic acid lactones | |
| Kanemoto et al. | Synthesis of (±)-2-fluorograndisol | |
| CA1273352A (en) | Intermediates useful in the preparation of hmg-coa reductase inhibitors | |
| Engebrecht | Chiral synthesis of alcohols via asymmetric epoxidation |