CN103168019B - 双环[2.2.2]辛-2-酮化合物的制备 - Google Patents

双环[2.2.2]辛-2-酮化合物的制备 Download PDF

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Publication number
CN103168019B
CN103168019B CN201180050144.2A CN201180050144A CN103168019B CN 103168019 B CN103168019 B CN 103168019B CN 201180050144 A CN201180050144 A CN 201180050144A CN 103168019 B CN103168019 B CN 103168019B
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compound
formula
phenyl
group
ester
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CN103168019A (zh
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斯黛芬·阿波勒
雅克-亚丽克西斯·富内尔
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Actelion Pharmaceuticals Ltd
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    • C—CHEMISTRY; METALLURGY
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • 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
    • C07C29/132—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07C45/27—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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07C45/51—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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • 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
    • C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • 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
    • C07C2602/44—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing eight carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
CN201180050144.2A 2010-10-20 2011-10-19 双环[2.2.2]辛-2-酮化合物的制备 Expired - Fee Related CN103168019B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IBPCT/IB2010/054747 2010-10-20
IB2010054747 2010-10-20
PCT/IB2011/054660 WO2012052939A2 (en) 2010-10-20 2011-10-19 Preparation of bicyclo[2.2.2]octan-2-one compounds

Publications (2)

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CN103168019A CN103168019A (zh) 2013-06-19
CN103168019B true CN103168019B (zh) 2015-05-27

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Country Link
US (1) US9296673B2 (enExample)
EP (1) EP2630111B1 (enExample)
JP (1) JP5909237B2 (enExample)
KR (1) KR101876594B1 (enExample)
CN (1) CN103168019B (enExample)
CA (1) CA2813131C (enExample)
DK (1) DK2630111T3 (enExample)
ES (1) ES2536897T3 (enExample)
HU (1) HUE025195T2 (enExample)
IL (1) IL225763A (enExample)
MX (1) MX2013004427A (enExample)
TW (2) TWI551583B (enExample)
WO (1) WO2012052939A2 (enExample)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2536897T3 (es) * 2010-10-20 2015-05-29 Actelion Pharmaceuticals Ltd. Preparación de compuestos de biciclo[2,2,2]octan-2-ona
KR101836552B1 (ko) 2010-10-20 2018-03-08 아이도시아 파마수티컬즈 리미티드 바이시클로[2.2.2]옥탄-2-온 화합물의 부분입체선택적 제조

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3046106A1 (de) * 1980-12-06 1982-07-15 Studiengesellschaft Kohle mbH, 4330 Mülheim Optisch reine bicyclo(2.2.2)oct-5-en-2.one, verfahren zu ihrer herstellung und ihre verwendung
JP3439255B2 (ja) * 1994-03-31 2003-08-25 長瀬産業株式会社 不斉マイケル反応を触媒する金属錯体
JP4595040B2 (ja) 2007-04-27 2010-12-08 アクテリオン ファーマシューティカルズ リミテッド 架橋６員環化合物
KR101364909B1 (ko) 2008-04-25 2014-02-21 액테리온 파마슈티칼 리미티드 칼슘 채널 차단제로서의 벤지미다졸 유도체
ES2536897T3 (es) * 2010-10-20 2015-05-29 Actelion Pharmaceuticals Ltd. Preparación de compuestos de biciclo[2,2,2]octan-2-ona
KR101836552B1 (ko) 2010-10-20 2018-03-08 아이도시아 파마수티컬즈 리미티드 바이시클로[2.2.2]옥탄-2-온 화합물의 부분입체선택적 제조

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Elusive 6-exo-Hydroxybicyclo[2.2.2]octan-2-ones from the Corresponding Acetates by Methanolysis in the Presence of CH3ONa/La(OTf)3;Stefano，et al.;《ORGANIC LETTERS》;20020713;第4卷(第16期);2783-2785 *
Johansson,et al..Metal-Catalyzed a-Arylation of Carbonyl and Related Molecules: Novel Trends in C-C Bond Formation by C-H Bond Functionalization.《Angewandt Chemie International Edition》.2010,第49卷676-707. *
Nikolay T. Tzvetkov,et al..Synthesis of optically active (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octan-2-one.《Tetrahedron: Asymmetry》.2006,第17卷993–998. *
On the Diastereoselectivity of the Aqueous-Acid-Catalyzed Intramolecular Aldol Condensation of 3-Oxocyclohexaneacetaldehydes;Barbara De Santis et al.;《Helvetica Chimica Acta》;19981216;第81卷;2375-2387 *
Synthesis of Bridged Steroids.III. Cholestane Derivatives having a Bridge Bicyclo[2.2.2]octane Ring System of the Atisine Type;Wataru Nagata，et al.;《Chemical & Pharmaceutical Bulletin》;19681231;第16卷(第5期);885-896 *

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Publication number Publication date
US20130211104A1 (en) 2013-08-15
CA2813131C (en) 2019-02-12
JP5909237B2 (ja) 2016-04-26
TWI551583B (zh) 2016-10-01
HUE025195T2 (en) 2016-02-29
IL225763A0 (en) 2013-06-27
KR101876594B1 (ko) 2018-08-02
JP2013544796A (ja) 2013-12-19
MX2013004427A (es) 2013-07-17
KR20130138268A (ko) 2013-12-18
WO2012052939A2 (en) 2012-04-26
ES2536897T3 (es) 2015-05-29
US9296673B2 (en) 2016-03-29
DK2630111T3 (en) 2015-04-20
TW201217324A (en) 2012-05-01
CA2813131A1 (en) 2012-04-26
EP2630111B1 (en) 2015-02-25
IL225763A (en) 2016-04-21
CN103168019A (zh) 2013-06-19
TWI511949B (zh) 2015-12-11
TW201217325A (en) 2012-05-01
WO2012052939A3 (en) 2012-06-21
EP2630111A2 (en) 2013-08-28

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