JP7036796B2 - 有機化合物 - Google Patents
有機化合物 Download PDFInfo
- Publication number
- JP7036796B2 JP7036796B2 JP2019508188A JP2019508188A JP7036796B2 JP 7036796 B2 JP7036796 B2 JP 7036796B2 JP 2019508188 A JP2019508188 A JP 2019508188A JP 2019508188 A JP2019508188 A JP 2019508188A JP 7036796 B2 JP7036796 B2 JP 7036796B2
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- JP
- Japan
- Prior art keywords
- methyl
- dihydro
- inden
- mmol
- nmr
- 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.)
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- 150000002894 organic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 95
- 239000000203 mixture Substances 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 34
- 239000003205 fragrance Substances 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 125000005394 methallyl group Chemical group 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- KCXNBYIRLUGZNP-UHFFFAOYSA-N 2,2-dimethyl-6-(2-methylpropyl)-3H-inden-1-one Chemical compound C(C(C)C)C1=CC=C2CC(C(C2=C1)=O)(C)C KCXNBYIRLUGZNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- NWYDCFZUSAAFDJ-UHFFFAOYSA-N 2-methyl-6-(2-methylpropoxy)-2,3-dihydroinden-1-one Chemical compound CC(C)COc1ccc2CC(C)C(=O)c2c1 NWYDCFZUSAAFDJ-UHFFFAOYSA-N 0.000 claims description 5
- WQMYPDSAFDCWDP-UHFFFAOYSA-N 2-methyl-6-propan-2-yl-2,3-dihydroinden-1-one Chemical compound CC(C)C1=CC=C2CC(C)C(=O)C2=C1 WQMYPDSAFDCWDP-UHFFFAOYSA-N 0.000 claims description 5
- MEKDVMIBVLKNGM-UHFFFAOYSA-N 6-cyclopropyl-2-methyl-2,3-dihydroinden-1-one Chemical compound C1=C2C(=O)C(C)CC2=CC=C1C1CC1 MEKDVMIBVLKNGM-UHFFFAOYSA-N 0.000 claims description 5
- CGGOCZOCSHPCRS-UHFFFAOYSA-N 2-methyl-6-propan-2-yloxy-2,3-dihydroinden-1-one Chemical compound CC(C)OC1=CC=C2CC(C)C(=O)C2=C1 CGGOCZOCSHPCRS-UHFFFAOYSA-N 0.000 claims description 4
- WOTCVCXPNQBBAZ-UHFFFAOYSA-N 2-methyl-6-propoxy-2,3-dihydroinden-1-one Chemical compound CCCOC1=CC=C2CC(C)C(=O)C2=C1 WOTCVCXPNQBBAZ-UHFFFAOYSA-N 0.000 claims description 4
- ZRPBLQBYLOYBTK-UHFFFAOYSA-N 2-methyl-6-propyl-2,3-dihydroinden-1-one Chemical compound CC1C(C2=CC(=CC=C2C1)CCC)=O ZRPBLQBYLOYBTK-UHFFFAOYSA-N 0.000 claims description 4
- TZDMMCXVGLCSSS-UHFFFAOYSA-N 6-butyl-2-methyl-2,3-dihydroinden-1-one Chemical compound CCCCc1ccc2CC(C)C(=O)c2c1 TZDMMCXVGLCSSS-UHFFFAOYSA-N 0.000 claims description 4
- ZABMAEZWPWOFED-UHFFFAOYSA-N 6-cyclopentyl-2-methyl-2,3-dihydroinden-1-one Chemical compound CC1CC2=CC=C(C=C2C1=O)C1CCCC1 ZABMAEZWPWOFED-UHFFFAOYSA-N 0.000 claims description 4
- JJARVPPFJKHTKJ-UHFFFAOYSA-N 6-ethyl-2-methyl-2,3-dihydroinden-1-one Chemical compound CCC1=CC=C2CC(C)C(=O)C2=C1 JJARVPPFJKHTKJ-UHFFFAOYSA-N 0.000 claims description 4
- WACXEYOYERMXDO-UHFFFAOYSA-N 6-tert-butyl-2-methyl-2,3-dihydroinden-1-one Chemical compound C1=C(C(C)(C)C)C=C2C(=O)C(C)CC2=C1 WACXEYOYERMXDO-UHFFFAOYSA-N 0.000 claims description 4
- IQHLLUZHVYLDHG-UHFFFAOYSA-N 2-ethyl-6-(2-methylpropyl)-2,3-dihydroinden-1-one Chemical compound C(C)C1C(C2=CC(=CC=C2C1)CC(C)C)=O IQHLLUZHVYLDHG-UHFFFAOYSA-N 0.000 claims description 3
- YRNAAQTZGDOVKZ-UHFFFAOYSA-N 6-ethoxy-2-methyl-2,3-dihydroinden-1-one Chemical compound CCOC1=CC=C2CC(C)C(=O)C2=C1 YRNAAQTZGDOVKZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims 1
- 239000000047 product Substances 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 31
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000007788 liquid Substances 0.000 description 21
- 238000004821 distillation Methods 0.000 description 19
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- -1 ethoxy, propoxy, isopropoxy, butoxy, isobutoxy Chemical group 0.000 description 16
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 13
- 239000012300 argon atmosphere Substances 0.000 description 13
- 241000220317 Rosa Species 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 239000012230 colorless oil Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- FAVMIAXKDIUAKF-UHFFFAOYSA-N 2-methyl-6-(2-methylpropyl)-2,3-dihydroinden-1-one Chemical compound CC(C)CC1=CC=C2CC(C)C(=O)C2=C1 FAVMIAXKDIUAKF-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 9
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000002304 perfume Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000002537 cosmetic Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- GMJKJIUETGRADG-UHFFFAOYSA-N 6-bromo-2-methyl-2,3-dihydroinden-1-one Chemical compound C1=C(Br)C=C2C(=O)C(C)CC2=C1 GMJKJIUETGRADG-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 5
- 150000002596 lactones Chemical class 0.000 description 5
- XFNJVKMNNVCYEK-UHFFFAOYSA-N 1-naphthaleneacetamide Chemical compound C1=CC=C2C(CC(=O)N)=CC=CC2=C1 XFNJVKMNNVCYEK-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- GMWXCOYOQNIWPE-UHFFFAOYSA-N 5-bromo-2-methyl-2,3-dihydroinden-1-one Chemical compound BrC1=CC=C2C(=O)C(C)CC2=C1 GMWXCOYOQNIWPE-UHFFFAOYSA-N 0.000 description 4
- QHKFBWKOHWQEFW-UHFFFAOYSA-N 7-bromo-2-methyl-2,3-dihydroinden-1-one Chemical compound C1=CC(Br)=C2C(=O)C(C)CC2=C1 QHKFBWKOHWQEFW-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLQFWPSBOBTKJX-UHFFFAOYSA-N 2,5-dimethyl-3-propan-2-ylhex-5-en-3-ol Chemical compound CC(C)C(O)(C(C)C)CC(C)=C XLQFWPSBOBTKJX-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- ZLJKMZTVEFFFDH-UHFFFAOYSA-N 2-methyl-7-propyl-2,3-dihydroinden-1-one Chemical compound CC1C(C2=C(C=CC=C2C1)CCC)=O ZLJKMZTVEFFFDH-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- CSDPIDNEKUGKRT-UHFFFAOYSA-N 3-methyl-6-(2-methylpropyl)-2,3-dihydroinden-1-one Chemical compound CC(C)CC1=CC=C2C(C)CC(=O)C2=C1 CSDPIDNEKUGKRT-UHFFFAOYSA-N 0.000 description 3
- XXLWDJVPTWFULT-UHFFFAOYSA-N 3-methyl-6-propyl-2,3-dihydroinden-1-one Chemical group CCCC1=CC=C2C(C)CC(=O)C2=C1 XXLWDJVPTWFULT-UHFFFAOYSA-N 0.000 description 3
- AHMJTIYXKJRVFF-UHFFFAOYSA-N 4-bromo-2-methyl-2,3-dihydroinden-1-one Chemical compound O=C1C(C)CC2=C1C=CC=C2Br AHMJTIYXKJRVFF-UHFFFAOYSA-N 0.000 description 3
- HBRMAARYSZHOQP-UHFFFAOYSA-N 5-cyclopropyl-2-methyl-2,3-dihydroinden-1-one Chemical compound C1(CC1)C=1C=C2CC(C(C2=CC=1)=O)C HBRMAARYSZHOQP-UHFFFAOYSA-N 0.000 description 3
- SJSHLFVUXUVDLA-UHFFFAOYSA-N 6-(2-methylpropyl)-2,3-dihydroinden-1-one Chemical compound CC(C)CC1=CC=C2CCC(=O)C2=C1 SJSHLFVUXUVDLA-UHFFFAOYSA-N 0.000 description 3
- MBPFQYUQOCHADH-UHFFFAOYSA-N 6-hydroxy-2-methyl-2,3-dihydroinden-1-one Chemical compound C1=C(O)C=C2C(=O)C(C)CC2=C1 MBPFQYUQOCHADH-UHFFFAOYSA-N 0.000 description 3
- QUNFVBXQKMUJDM-UHFFFAOYSA-N 6a-methyl-4-(2-methylpropyl)-1,1a-dihydrocyclopropa[a]inden-6-one Chemical compound CC(C)Cc1ccc2C3CC3(C)C(=O)c2c1 QUNFVBXQKMUJDM-UHFFFAOYSA-N 0.000 description 3
- OWIMJKZFHNTZPQ-UHFFFAOYSA-N 7-cyclopropyl-2-methyl-2,3-dihydroinden-1-one Chemical compound C1(CC1)C=1C=CC=C2CC(C(C=12)=O)C OWIMJKZFHNTZPQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- 235000010254 Jasminum officinale Nutrition 0.000 description 3
- 240000005385 Jasminum sambac Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940022663 acetate Drugs 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000005923 long-lasting effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- CRDAMVZIKSXKFV-GNESMGCMSA-N (2-trans,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C\CO CRDAMVZIKSXKFV-GNESMGCMSA-N 0.000 description 2
- GLZPCOQZEFWAFX-JXMROGBWSA-N (E)-Geraniol Chemical compound CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 2
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
- BVDMQAQCEBGIJR-UHFFFAOYSA-N 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol Chemical compound CCCC(O)CCC1C(C)CCCC1(C)C BVDMQAQCEBGIJR-UHFFFAOYSA-N 0.000 description 2
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 2
- BZAASELHDAYVFJ-UHFFFAOYSA-N 2,3-dimethyl-6-propyl-2,3-dihydroinden-1-one Chemical compound CCCC1=CC=C2C(C)C(C)C(=O)C2=C1 BZAASELHDAYVFJ-UHFFFAOYSA-N 0.000 description 2
- WQTWCOYXJRWQNN-UHFFFAOYSA-N 2-methyl-3-[4-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=C(CC(C)C(O)=O)C=C1 WQTWCOYXJRWQNN-UHFFFAOYSA-N 0.000 description 2
- VFGQZJSMTDZJDK-UHFFFAOYSA-N 2-methyl-4-propyl-2,3-dihydroinden-1-one Chemical compound CC1C(C2=CC=CC(=C2C1)CCC)=O VFGQZJSMTDZJDK-UHFFFAOYSA-N 0.000 description 2
- NKAXYYKVNOMNJN-UHFFFAOYSA-N 2-methyl-5-(2-methylpropyl)-2,3-dihydroinden-1-one Chemical compound CC(C)CC1=CC=C2C(=O)C(C)CC2=C1 NKAXYYKVNOMNJN-UHFFFAOYSA-N 0.000 description 2
- SORMENWWIVHSFD-UHFFFAOYSA-N 2-methyl-5-propyl-2,3-dihydroinden-1-one Chemical compound CC1C(C2=CC=C(C=C2C1)CCC)=O SORMENWWIVHSFD-UHFFFAOYSA-N 0.000 description 2
- ZAZPDOYUCVFPOI-UHFFFAOYSA-N 2-methylpropylboronic acid Chemical compound CC(C)CB(O)O ZAZPDOYUCVFPOI-UHFFFAOYSA-N 0.000 description 2
- NGYMOTOXXHCHOC-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CC(O)C(C)CCC1CC=C(C)C1(C)C NGYMOTOXXHCHOC-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- SEQHEDQNODAFIU-UHFFFAOYSA-N 6-bromo-2,3-dihydroinden-1-one Chemical compound BrC1=CC=C2CCC(=O)C2=C1 SEQHEDQNODAFIU-UHFFFAOYSA-N 0.000 description 2
- IXZBLOSMMNBZAP-UHFFFAOYSA-N 6-butan-2-yl-2-methyl-2,3-dihydroinden-1-one Chemical compound CCC(C)c1ccc2CC(C)C(=O)c2c1 IXZBLOSMMNBZAP-UHFFFAOYSA-N 0.000 description 2
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- 239000002775 capsule Substances 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- VTTDFSNKIMAQTB-UHFFFAOYSA-N cyclopentylboronic acid Chemical compound OB(O)C1CCCC1 VTTDFSNKIMAQTB-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
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- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
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- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
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- 238000005538 encapsulation Methods 0.000 description 1
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- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 description 1
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- 229940020436 gamma-undecalactone Drugs 0.000 description 1
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- 239000000543 intermediate Substances 0.000 description 1
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- 239000010656 jasmine oil Substances 0.000 description 1
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- 239000012074 organic phase Substances 0.000 description 1
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- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- 239000003380 propellant Substances 0.000 description 1
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- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- 229940116411 terpineol Drugs 0.000 description 1
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- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Wood Science & Technology (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2016/095273 | 2016-08-15 | ||
| CN2016095273 | 2016-08-15 | ||
| PCT/EP2017/070593 WO2017191331A2 (en) | 2016-08-15 | 2017-08-14 | Organic compounds |
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| Publication Number | Publication Date |
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| JP2019532123A JP2019532123A (ja) | 2019-11-07 |
| JP2019532123A5 JP2019532123A5 (enExample) | 2020-09-24 |
| JP7036796B2 true JP7036796B2 (ja) | 2022-03-15 |
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| JP2019508188A Active JP7036796B2 (ja) | 2016-08-15 | 2017-08-14 | 有機化合物 |
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| EP (1) | EP3497192B1 (enExample) |
| JP (1) | JP7036796B2 (enExample) |
| CN (1) | CN109563438B (enExample) |
| ES (1) | ES2908129T3 (enExample) |
| MX (1) | MX384407B (enExample) |
| SG (1) | SG11201900424SA (enExample) |
| WO (1) | WO2017191331A2 (enExample) |
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| ES2908129T3 (es) | 2016-08-15 | 2022-04-27 | Givaudan Sa | Compuestos orgánicos |
| MX2019000984A (es) * | 2016-08-15 | 2019-07-04 | Givaudan Sa | Proceso para preparacion de indanonas. |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000212111A (ja) | 1999-01-22 | 2000-08-02 | Firmenich Sa | ２―インダンメタノ―ル誘導体、その使用、香料組成物、賦香製品、該化合物の製造方法および出発化合物 |
| US20030125584A1 (en) | 2001-11-12 | 2003-07-03 | Steffen Sonnenberg | 6-Alkylindan-1-ones as fragrances |
| JP2005097198A (ja) | 2003-09-26 | 2005-04-14 | National Institute Of Advanced Industrial & Technology | １−インダノン類の製造方法 |
| JP2005519081A (ja) | 2002-02-28 | 2005-06-30 | ジボダン エス エー | インダンおよびインダノンならびにそれらの香料における使用 |
| WO2016113151A1 (en) | 2015-01-12 | 2016-07-21 | Firmenich Sa | Intermediate compounds for producing perfuming ingredients |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3944679A (en) | 1973-04-13 | 1976-03-16 | The Japan Tobacco & Salt Public Corporation | Process for imparting a coumarin-like aroma and flavor to tobacco, foods and drinks |
| JPS5248200B2 (enExample) * | 1973-04-13 | 1977-12-08 | ||
| US4572796A (en) * | 1984-05-24 | 1986-02-25 | International Flavors & Fragrances Inc. | 1,1,4,7-Tetramethyl-3-indanone, product produced thereby and organoleptic uses thereof |
| US5012007A (en) * | 1989-10-05 | 1991-04-30 | Varadaraj Elango | Method for producing 1-indanone derivatives |
| ATE140442T1 (de) * | 1992-04-28 | 1996-08-15 | Hoechst Ag | Verfahren zur herstellung substituierter indanone und ihre verwendung |
| EP0582194B1 (de) | 1992-08-03 | 1998-05-06 | TARGOR GmbH | Verfahren zur Herstellung eines Olefinpolymers unter Verwendung von Metallocenen mit speziell substituierten Indenylliganden |
| DE69516036T2 (de) * | 1994-05-31 | 2000-12-21 | Firmenich S.A., Genf/Geneve | Aromatische Verbindungen und ihre Verwendung in der Parfümerie |
| US5998477A (en) | 1996-06-13 | 1999-12-07 | Cell Pathways Inc. | Substituted methoxy benzylidene indenyl-acetic and propionic acids for treating patients with precancerous lesions |
| GB201115409D0 (en) * | 2011-09-07 | 2011-10-19 | Givaudan Sa | Organic compounds |
| EA201590356A1 (ru) | 2012-08-16 | 2015-07-30 | Байер Фарма Акциенгезельшафт | 2,3-бензодиазепины |
| WO2014096282A1 (en) | 2012-12-21 | 2014-06-26 | Borealis Ag | Catalyst |
| ES2908129T3 (es) | 2016-08-15 | 2022-04-27 | Givaudan Sa | Compuestos orgánicos |
-
2017
- 2017-08-14 ES ES17757712T patent/ES2908129T3/es active Active
- 2017-08-14 SG SG11201900424SA patent/SG11201900424SA/en unknown
- 2017-08-14 JP JP2019508188A patent/JP7036796B2/ja active Active
- 2017-08-14 EP EP17757712.9A patent/EP3497192B1/en active Active
- 2017-08-14 WO PCT/EP2017/070593 patent/WO2017191331A2/en not_active Ceased
- 2017-08-14 US US16/321,653 patent/US11020333B2/en active Active
- 2017-08-14 MX MX2019001303A patent/MX384407B/es unknown
- 2017-08-14 CN CN201780049981.0A patent/CN109563438B/zh active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000212111A (ja) | 1999-01-22 | 2000-08-02 | Firmenich Sa | ２―インダンメタノ―ル誘導体、その使用、香料組成物、賦香製品、該化合物の製造方法および出発化合物 |
| US20030125584A1 (en) | 2001-11-12 | 2003-07-03 | Steffen Sonnenberg | 6-Alkylindan-1-ones as fragrances |
| JP2005519081A (ja) | 2002-02-28 | 2005-06-30 | ジボダン エス エー | インダンおよびインダノンならびにそれらの香料における使用 |
| JP2005097198A (ja) | 2003-09-26 | 2005-04-14 | National Institute Of Advanced Industrial & Technology | １−インダノン類の製造方法 |
| WO2016113151A1 (en) | 2015-01-12 | 2016-07-21 | Firmenich Sa | Intermediate compounds for producing perfuming ingredients |
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| LAMBOLEY, S. et al.，HELVETICA CHIMICA ACTA，2004年，(2004), vol.87, No.7，pp.1767-1793 |
| PREMASAGAR, V. et al.，J, Org. Chem.，1981年，(1981), Vol.46，pp.2974-2976 |
Also Published As
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|---|---|
| US11020333B2 (en) | 2021-06-01 |
| US20200330346A1 (en) | 2020-10-22 |
| EP3497192A2 (en) | 2019-06-19 |
| WO2017191331A3 (en) | 2017-12-14 |
| ES2908129T3 (es) | 2022-04-27 |
| JP2019532123A (ja) | 2019-11-07 |
| CN109563438A (zh) | 2019-04-02 |
| SG11201900424SA (en) | 2019-02-27 |
| CN109563438B (zh) | 2022-11-04 |
| WO2017191331A2 (en) | 2017-11-09 |
| EP3497192B1 (en) | 2021-12-22 |
| MX384407B (es) | 2025-03-14 |
| MX2019001303A (es) | 2019-06-17 |
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