JP2017537965A5 - - Google Patents
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- JP2017537965A5 JP2017537965A5 JP2017532651A JP2017532651A JP2017537965A5 JP 2017537965 A5 JP2017537965 A5 JP 2017537965A5 JP 2017532651 A JP2017532651 A JP 2017532651A JP 2017532651 A JP2017532651 A JP 2017532651A JP 2017537965 A5 JP2017537965 A5 JP 2017537965A5
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- JP
- Japan
- Prior art keywords
- aryl
- alkyl
- unsubstituted
- group
- cycloalkyl
- 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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- 238000000034 method Methods 0.000 claims 19
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000002947 alkylene group Chemical group 0.000 claims 11
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims 10
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 239000003446 ligand Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 5
- 239000007789 gas Substances 0.000 claims 4
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- WTEVQBCEXWBHNA-YFHOEESVSA-N citral B Natural products CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 claims 3
- 229930003633 citronellal Natural products 0.000 claims 3
- 235000000983 citronellal Nutrition 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- 238000005984 hydrogenation reaction Methods 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims 2
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 claims 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims 2
- 241000134874 Geraniales Species 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229940095045 isopulegol Drugs 0.000 claims 2
- 229940041616 menthol Drugs 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- ZYTMANIQRDEHIO-UHFFFAOYSA-N neo-Isopulegol Natural products CC1CCC(C(C)=C)C(O)C1 ZYTMANIQRDEHIO-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052703 rhodium Inorganic materials 0.000 claims 2
- 239000010948 rhodium Substances 0.000 claims 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 229910052723 transition metal Inorganic materials 0.000 claims 2
- 150000003624 transition metals Chemical class 0.000 claims 2
- -1 where Chemical group 0.000 claims 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000010952 in-situ formation Methods 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 150000003284 rhodium compounds Chemical class 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- CMCIANULETZYAX-UHFFFAOYSA-N C(C1C(C2)C34)C1C2C3C4(P(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1 Chemical compound C(C1C(C2)C34)C1C2C3C4(P(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1 CMCIANULETZYAX-UHFFFAOYSA-N 0.000 description 1
- 0 CC(*)[C@@](C)P(c1ccccc1)c1ccccc1 Chemical compound CC(*)[C@@](C)P(c1ccccc1)c1ccccc1 0.000 description 1
- BZCRVNJZUUYVJM-UHFFFAOYSA-N CC(CC(C1)C2(C3)P(c4ccccc4)c4ccccc4)C1C23P(c1ccccc1)c1ccccc1 Chemical compound CC(CC(C1)C2(C3)P(c4ccccc4)c4ccccc4)C1C23P(c1ccccc1)c1ccccc1 BZCRVNJZUUYVJM-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14199410 | 2014-12-19 | ||
| EP14199410.3 | 2014-12-19 | ||
| PCT/EP2015/080392 WO2016097242A1 (de) | 2014-12-19 | 2015-12-18 | Verfahren zur herstellung optisch aktiver carbonylverbindungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017537965A JP2017537965A (ja) | 2017-12-21 |
| JP2017537965A5 true JP2017537965A5 (enExample) | 2019-02-07 |
| JP6702974B2 JP6702974B2 (ja) | 2020-06-03 |
Family
ID=52231936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017532651A Active JP6702974B2 (ja) | 2014-12-19 | 2015-12-18 | 光学活性カルボニル化合物を合成する方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US9975837B2 (enExample) |
| EP (2) | EP3233778B1 (enExample) |
| JP (1) | JP6702974B2 (enExample) |
| CN (1) | CN107250091B (enExample) |
| ES (2) | ES2883557T3 (enExample) |
| MX (1) | MX375969B (enExample) |
| WO (1) | WO2016097242A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016177814A1 (en) | 2015-05-04 | 2016-11-10 | Basf Se | Process for the preparation of melonal |
| JP2018533564A (ja) | 2015-10-12 | 2018-11-15 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | １，６−二置換ヘキサン誘導体を製造するためのヒドロホルミル化法 |
| PL3386919T3 (pl) | 2015-12-08 | 2022-02-21 | Basf Se | Zawierający cynę materiał zeolitowy o strukturze szkieletowej bea |
| ES2844182T3 (es) | 2016-06-07 | 2021-07-21 | Basf Se | Procedimiento para la preparación de alcoholes con insaturación en posición 2,3 |
| JP7039498B2 (ja) | 2016-06-29 | 2022-03-22 | ビーエーエスエフ ソシエタス・ヨーロピア | 液相の存在下でのアルコールの酸化によるアルファ，ベータ不飽和アルデヒドの製造方法 |
| EP3523267B1 (de) | 2016-10-06 | 2020-12-09 | Basf Se | Verfahren zur anreicherung von enantiomeren aus einem enantiomerengemisch |
| JP2021506870A (ja) * | 2017-12-21 | 2021-02-22 | ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ | 液相の存在下でのアルコールの酸化によるα，β不飽和アルデヒドの製造方法 |
| MY205693A (en) * | 2018-09-05 | 2024-11-07 | Basf Se | Reactor for carrying out a gas-liquid two-phase high-pressure reaction with a foaming medium |
| EP3846927B1 (de) | 2018-09-05 | 2022-11-23 | Basf Se | Reaktor zur durchführung einer reaktion zwischen zwei nicht mischbaren fluiden unterschiedlicher dichte |
| MX2021002670A (es) * | 2018-09-05 | 2021-05-12 | Basf Se | Preparacion continua de un compuesto de carbonilo opticamente activo mediante hidrogenacion asimetrica. |
| CN112770834B (zh) * | 2018-09-05 | 2023-07-21 | 巴斯夫欧洲公司 | 进行气/液两相高压反应的方法 |
| WO2020239721A1 (en) * | 2019-05-27 | 2020-12-03 | Dsm Ip Assets B.V. | Selective hydrogenation of alkynes to alkenes in the presence of a phosphorus compound and an organic sulphur compound |
| CN111056932A (zh) * | 2019-12-09 | 2020-04-24 | 万华化学集团股份有限公司 | 一种制备光学活性香茅醛的方法 |
| US12202792B2 (en) | 2019-12-09 | 2025-01-21 | Wanhua Chemical Group Co., Ltd. | Preparation method for optically active citronellal |
| CN110872217A (zh) * | 2019-12-09 | 2020-03-10 | 万华化学集团股份有限公司 | 一种光学活性的香茅醛的制备方法 |
| CN111004102B (zh) * | 2019-12-23 | 2022-11-04 | 万华化学集团股份有限公司 | 一种制备光学活性香茅醛的方法及用于该方法的催化剂 |
| CN111056933B (zh) * | 2019-12-24 | 2022-11-08 | 万华化学集团股份有限公司 | 一种制备光学活性香茅醛的方法及用于该方法的催化剂体系 |
| CN111792986B (zh) * | 2020-07-22 | 2022-09-20 | 万华化学集团股份有限公司 | 一种制备r-香茅醛的方法 |
| CN112142583B (zh) * | 2020-10-26 | 2022-07-26 | 万华化学集团股份有限公司 | 一种香叶醛制备橙花醛的方法 |
| CN113527367B (zh) * | 2021-07-14 | 2022-08-02 | 南开沧州渤海新区绿色化工研究有限公司 | 一种含四（3,5-二三氟甲基苯基）硼阴离子的手性双膦配体铑络合物和制备方法及应用 |
| WO2025011972A1 (en) | 2023-07-07 | 2025-01-16 | Basf Se | Photoisomerization of geranial and neral |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4115417A (en) * | 1975-10-16 | 1978-09-19 | Hoffmann-La Roche Inc. | Asymmetric hydrogenation catalyzed by rhodium complexes of chiral tertiary phosphines |
| JPS5278812A (en) | 1975-12-26 | 1977-07-02 | Nikki Chem Co Ltd | Selective production method of saturated aldehyde |
| FR2396735A1 (fr) * | 1977-07-04 | 1979-02-02 | Rhone Poulenc Ind | Procede de preparation de citronellal optiquement actif |
| DE19854637A1 (de) | 1998-11-26 | 2000-05-31 | Basf Ag | Reaktor zur kontinuierlichen Durchführung von Gas-Flüssig-, Flüssig-Flüssig- oder Gas-Flüssig-Fest-Reaktionen |
| JP4676617B2 (ja) | 2001-01-18 | 2011-04-27 | 高砂香料工業株式会社 | イソプレゴールの製造方法 |
| DE102004049631A1 (de) | 2004-10-11 | 2006-04-20 | Basf Ag | Verfahren zur Herstellung optisch aktiver Carbonylverbindungen |
| DE102004057277A1 (de) | 2004-11-26 | 2006-06-01 | Basf Ag | Verfahren zur Herstellung von Menthol |
| US7973198B2 (en) | 2007-04-25 | 2011-07-05 | Basf Se | Method for synthesizing optically active carbonyl compounds |
| PE20091364A1 (es) * | 2008-01-17 | 2009-10-13 | Novartis Ag | Proceso para la preparacion de inhibidores de nep |
| JP5711209B2 (ja) * | 2010-03-04 | 2015-04-30 | 高砂香料工業株式会社 | 均一系不斉水素化触媒 |
-
2015
- 2015-12-18 US US15/536,524 patent/US9975837B2/en active Active
- 2015-12-18 CN CN201580076501.0A patent/CN107250091B/zh active Active
- 2015-12-18 ES ES18206833T patent/ES2883557T3/es active Active
- 2015-12-18 EP EP15817247.8A patent/EP3233778B1/de active Active
- 2015-12-18 EP EP18206833.8A patent/EP3489213B1/de active Active
- 2015-12-18 JP JP2017532651A patent/JP6702974B2/ja active Active
- 2015-12-18 ES ES15817247T patent/ES2727384T3/es active Active
- 2015-12-18 MX MX2017008170A patent/MX375969B/es active IP Right Grant
- 2015-12-18 WO PCT/EP2015/080392 patent/WO2016097242A1/de not_active Ceased
-
2018
- 2018-04-27 US US15/964,400 patent/US10301244B2/en not_active Ceased
-
2019
- 2019-07-25 US US16/521,935 patent/USRE49036E1/en active Active
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