CN102036941B - 用于制备β-檀香醇及其衍生物的方法 - Google Patents

用于制备β-檀香醇及其衍生物的方法 Download PDF

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CN102036941B
CN102036941B CN200980118062XA CN200980118062A CN102036941B CN 102036941 B CN102036941 B CN 102036941B CN 200980118062X A CN200980118062X A CN 200980118062XA CN 200980118062 A CN200980118062 A CN 200980118062A CN 102036941 B CN102036941 B CN 102036941B
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CN102036941A (zh
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C·费尔
M·弗亚纽
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Firmenich SA
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
    • C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
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    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
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    • C07—ORGANIC CHEMISTRY
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    • 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
    • C07C29/38—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 by reaction with aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/75—Reactions with formaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/283—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Catalysts (AREA)
CN200980118062XA 2008-05-20 2009-05-18 用于制备β-檀香醇及其衍生物的方法 Active CN102036941B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP08104028 2008-05-20
EP08104028.9 2008-05-20
PCT/IB2009/052048 WO2009141781A1 (en) 2008-05-20 2009-05-18 Process for the preparation of beta-santalol and derivatives thereof

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CN102036941A CN102036941A (zh) 2011-04-27
CN102036941B true CN102036941B (zh) 2013-07-31

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US (2) US7902393B2 (enExample)
EP (2) EP2386537B1 (enExample)
JP (2) JP5550637B2 (enExample)
CN (1) CN102036941B (enExample)
AT (1) ATE527228T1 (enExample)
ES (2) ES2372911T3 (enExample)
IL (2) IL209363A (enExample)
WO (1) WO2009141781A1 (enExample)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103384655B (zh) * 2011-02-16 2015-04-15 弗门尼舍有限公司 用于制备β-檀香醇的中间体
EP2726447B1 (en) * 2011-06-30 2015-08-12 Firmenich SA Process for the preparation of beta-santalol
US9156770B2 (en) * 2011-06-30 2015-10-13 Firmenich Sa Process for the preparation of beta-santalol
CN105705478B (zh) * 2013-11-11 2018-10-12 弗门尼舍有限公司 具有木质气味的化合物
US9958504B2 (en) 2014-06-20 2018-05-01 Duracell U.S. Operations, Inc. Primary alkaline battery with integrated in-cell resistances
ES2709926T3 (es) * 2014-12-02 2019-04-22 Firmenich & Cie Intermedios y procedimiento para la preparación de bloques de construcción de aceite de sándalo
CN117843453A (zh) * 2022-09-30 2024-04-09 中国科学院大连化学物理研究所 一种2-亚龙脑烯基丁醇的制备方法

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US3662008A (en) * 1969-05-21 1972-05-09 Procter & Gamble Process for preparing beta-santalol from 3-methylnorcamphor
US4223167A (en) * 1978-02-14 1980-09-16 Fritzsche Dodge & Olcott Inc. Processes for preparing β-santalol, β-santalene dihydro-β-santalol and related compounds
DE2843838A1 (de) 1978-10-07 1980-04-24 Basf Ag Bicyclische verbindungen, verfahren zu deren herstellung und deren verwendung
JPS5738730A (en) * 1980-08-14 1982-03-03 Kuraray Co Ltd Cis-pentene derivative and its preparation
JPS5742659A (en) * 1980-08-28 1982-03-10 Kuraray Co Ltd Bicyclo 2 2 1 heptane derivative and its preparation
US4510319A (en) * 1982-07-01 1985-04-09 Fritzsche Dodge & Olcott Inc. Functionalization of terminal trisubstituted alkenes and derivatives thereof
FR2621912B1 (fr) * 1987-10-16 1990-03-02 Oreal Nouveaux derives du norbornane, leur procede de preparation et compositions cosmetique et medicamenteuse les contenant
JP2929943B2 (ja) * 1994-09-07 1999-08-03 ダイソー株式会社 カルシトリオール中間体及びその製法
AU2002320231A1 (en) 2001-06-29 2003-03-03 California Institute Of Technology Enantioselective transformation of alpha, beta-unsaturated aldehydes using chiral organic catalysts
DE10348062A1 (de) * 2003-10-16 2005-05-19 Symrise Gmbh & Co. Kg Kurzkettige Enolester als Riechstoff-Prekursoren
US7112700B1 (en) * 2005-04-14 2006-09-26 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Efficient and economic asymmetric synthesis of nootkatone, tetrahydronootkatone, their precursors and derivatives
CN101641310B (zh) * 2007-04-03 2013-07-24 弗门尼舍有限公司 使用钌络合物进行的二烯的1,4-氢化

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AchimKrotzandGúnterHelmchen.TotalSynthesesofSandalwoodFragrances:(Z)-and(E)-B-SantalolandTheirEnantiomers ent-B-Santalene.《Tetrahedron: Asymmetry》.1990
Herbert C.Kretschmar and William F.Erman.THE TOTAL SYNTHESIS AND GEOMETRIC CONFIGURATION OF dl-β-SANTALOL.《Tetrahedron Letters》.1970,(第1期),41-44.
THE TOTAL SYNTHESIS AND GEOMETRIC CONFIGURATION OF dl-β-SANTALOL;Herbert C.Kretschmar and William F.Erman;《Tetrahedron Letters》;19701231(第1期);41-44 *
Total Syntheses of Sandalwood Fragrances: (Z)- and (E)-B-Santalol and Their Enantiomers,ent-B-Santalene;Achim Krotz and Gúnter Helmchen;《Tetrahedron: Asymmetry》;19901231;第1卷(第8期);537-540 *

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US20110118497A1 (en) 2011-05-19
IL226276A0 (en) 2013-06-27
EP2386537A3 (en) 2012-01-11
JP5717893B2 (ja) 2015-05-13
EP2386537B1 (en) 2013-01-16
JP2014098019A (ja) 2014-05-29
ES2372911T3 (es) 2012-01-27
IL209363A0 (en) 2011-01-31
US20110028750A1 (en) 2011-02-03
JP5550637B2 (ja) 2014-07-16
ES2401986T3 (es) 2013-04-26
JP2011520950A (ja) 2011-07-21
US7902393B2 (en) 2011-03-08
CN102036941A (zh) 2011-04-27
EP2386537A2 (en) 2011-11-16
EP2282985B1 (en) 2011-10-05
IL209363A (en) 2014-04-30
WO2009141781A1 (en) 2009-11-26
US8119826B2 (en) 2012-02-21
ATE527228T1 (de) 2011-10-15
EP2282985A1 (en) 2011-02-16

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