JP2010536802A5 - - Google Patents
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- Publication number
- JP2010536802A5 JP2010536802A5 JP2010521276A JP2010521276A JP2010536802A5 JP 2010536802 A5 JP2010536802 A5 JP 2010536802A5 JP 2010521276 A JP2010521276 A JP 2010521276A JP 2010521276 A JP2010521276 A JP 2010521276A JP 2010536802 A5 JP2010536802 A5 JP 2010536802A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopropanation
- dibromomethane
- positions
- ether solvent
- alcoholate
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 11
- 238000000034 method Methods 0.000 claims 8
- 238000005888 cyclopropanation reaction Methods 0.000 claims 6
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 150000004795 grignard reagents Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 239000007818 Grignard reagent Substances 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical class OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- WCASXYBKJHWFMY-UHFFFAOYSA-N crotyl alcohol Chemical compound CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- KJIOYTCLMVWFEZ-UHFFFAOYSA-N 1-(2,2-dimethyl-6-bicyclo[4.1.0]heptanyl)ethanol Chemical compound CC1(C)CCCC2(C(O)C)C1C2 KJIOYTCLMVWFEZ-UHFFFAOYSA-N 0.000 claims 1
- JTWAPXXPIVWBGT-UHFFFAOYSA-N 1-(2-ethylcyclopropyl)propan-2-ol Chemical compound CCC1CC1CC(C)O JTWAPXXPIVWBGT-UHFFFAOYSA-N 0.000 claims 1
- VGNSBDAOHLYXFB-UHFFFAOYSA-N 1-ethyl-4,5-dimethylbicyclo[3.1.0]hexan-4-ol Chemical compound CC1(O)CCC2(CC)C1(C)C2 VGNSBDAOHLYXFB-UHFFFAOYSA-N 0.000 claims 1
- -1 2,2,5a, 7a-tetramethyldecahydro-1H-dicyclopropa [b, d] naphthalen-6a-yl Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- OAKFACUIGQLOCA-UHFFFAOYSA-N [1-methyl-2-[(1,2,2-trimethyl-3-bicyclo[3.1.0]hexanyl)methyl]cyclopropyl]methanol Chemical compound OCC1(C)CC1CC1C(C)(C)C2(C)CC2C1 OAKFACUIGQLOCA-UHFFFAOYSA-N 0.000 claims 1
- NWFDYJDCSIHFAB-UHFFFAOYSA-M [Cl-].CCC(C)(C)[Mg+] Chemical compound [Cl-].CCC(C)(C)[Mg+] NWFDYJDCSIHFAB-UHFFFAOYSA-M 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 235000019634 flavors Nutrition 0.000 claims 1
- 239000003205 fragrance Substances 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical group [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- FNORHVDKJWGANC-UHFFFAOYSA-N undecan-4-ol Chemical compound CCCCCCCC(O)CCC FNORHVDKJWGANC-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0716232.4 | 2007-08-21 | ||
| GBGB0716232.4A GB0716232D0 (en) | 2007-08-21 | 2007-08-21 | Cyclopropanation process |
| PCT/CH2008/000352 WO2009023980A1 (en) | 2007-08-21 | 2008-08-19 | Cyclopropanation process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010536802A JP2010536802A (ja) | 2010-12-02 |
| JP2010536802A5 true JP2010536802A5 (OSRAM) | 2011-10-06 |
| JP5442612B2 JP5442612B2 (ja) | 2014-03-12 |
Family
ID=38566689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010521276A Expired - Fee Related JP5442612B2 (ja) | 2007-08-21 | 2008-08-19 | シクロプロパン化方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8450533B2 (OSRAM) |
| EP (1) | EP2190803A1 (OSRAM) |
| JP (1) | JP5442612B2 (OSRAM) |
| CN (1) | CN101784509B (OSRAM) |
| BR (1) | BRPI0816237A2 (OSRAM) |
| GB (1) | GB0716232D0 (OSRAM) |
| MX (1) | MX2010001476A (OSRAM) |
| WO (1) | WO2009023980A1 (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0916363D0 (en) * | 2009-09-18 | 2009-10-28 | Givaudan Sa | Organic compounds |
| JP5027937B2 (ja) * | 2011-01-31 | 2012-09-19 | 小川香料株式会社 | 香料組成物 |
| WO2012159223A1 (en) * | 2011-05-25 | 2012-11-29 | Givaudan Sa | Trimethyloctadienol and derivatives thereof used as fragrance ingredient |
| US9296675B2 (en) * | 2013-03-12 | 2016-03-29 | Takasago International Corporation | Compound having cyclopropane ring, and flavor and/or fragrance composition containing same |
| WO2017024126A1 (en) * | 2015-08-06 | 2017-02-09 | International Flavors & Fragrances Inc. | Cyclopropanation of substituted alkenes |
| JP6091028B1 (ja) * | 2015-11-11 | 2017-03-08 | 花王株式会社 | シクロプロパン化合物 |
| US10584080B2 (en) | 2017-12-12 | 2020-03-10 | International Flavors & Fragrances Inc. | Cyclopropanation of substituted alkenes |
| CN112920017B (zh) * | 2021-01-27 | 2022-09-02 | 格林生物科技股份有限公司 | 一种双环丙烷基衍生化合物的制备方法 |
| US20250326984A1 (en) | 2022-06-01 | 2025-10-23 | Symrise Ag | Fragrances with cyclopropyl structure |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2517586A1 (de) | 1974-05-08 | 1975-11-20 | Hoffmann La Roche | Bicyclische verbindungen |
| GB8729107D0 (en) * | 1987-12-14 | 1988-01-27 | Ici Plc | Chemical process |
| KR20070089195A (ko) | 2004-12-24 | 2007-08-30 | 지보당 에스아 | 사이클로프로판화 방법 |
| US7410942B2 (en) | 2005-02-24 | 2008-08-12 | International Flavors & Fragrances Inc. | Substituted 1-(2-ethyl-1-methyl-cyclopropyl)-one/ol derivatives |
| GB0515926D0 (en) | 2005-08-03 | 2005-09-07 | Merck Sharp & Dohme | Chemical process |
| EP2181085A1 (en) * | 2006-04-03 | 2010-05-05 | Flexitral, Inc. | Cyclopropanated aromachemicals |
-
2007
- 2007-08-21 GB GBGB0716232.4A patent/GB0716232D0/en not_active Ceased
-
2008
- 2008-08-19 EP EP08783452A patent/EP2190803A1/en not_active Withdrawn
- 2008-08-19 MX MX2010001476A patent/MX2010001476A/es active IP Right Grant
- 2008-08-19 JP JP2010521276A patent/JP5442612B2/ja not_active Expired - Fee Related
- 2008-08-19 US US12/673,901 patent/US8450533B2/en not_active Expired - Fee Related
- 2008-08-19 WO PCT/CH2008/000352 patent/WO2009023980A1/en not_active Ceased
- 2008-08-19 BR BRPI0816237-9A2A patent/BRPI0816237A2/pt not_active Application Discontinuation
- 2008-08-19 CN CN2008801037025A patent/CN101784509B/zh not_active Expired - Fee Related
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