CN103153947B - 非对映选择性制备双环[2.2.2]辛-2-酮化合物 - Google Patents

非对映选择性制备双环[2.2.2]辛-2-酮化合物 Download PDF

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Publication number
CN103153947B
CN103153947B CN201180047343.8A CN201180047343A CN103153947B CN 103153947 B CN103153947 B CN 103153947B CN 201180047343 A CN201180047343 A CN 201180047343A CN 103153947 B CN103153947 B CN 103153947B
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compound
formula
achiral
base
solvent
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Chinese (zh)
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CN103153947A (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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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
    • C07C45/64—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 introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/20—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to carbon atoms of rings other than six-membered aromatic 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
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/25—Sulfonic acids having sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings of a carbon skeleton
    • 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
    • C07C45/61—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
    • 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
    • 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
    • C07C2602/44—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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CN201180047343.8A 2010-10-20 2011-10-19 非对映选择性制备双环[2.2.2]辛-2-酮化合物 Expired - Fee Related CN103153947B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IBPCT/IB2010/054743 2010-10-20
IB2010054743 2010-10-20
PCT/IB2011/054666 WO2012052943A1 (en) 2010-10-20 2011-10-19 Diastereoselective preparation of bicyclo[2.2.2]octan-2-one compounds

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Publication Number Publication Date
CN103153947A CN103153947A (zh) 2013-06-12
CN103153947B true CN103153947B (zh) 2015-11-25

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CN201180047343.8A Expired - Fee Related CN103153947B (zh) 2010-10-20 2011-10-19 非对映选择性制备双环[2.2.2]辛-2-酮化合物

Country Status (11)

Country Link
US (1) US8816118B2 (enExample)
EP (1) EP2630120B1 (enExample)
JP (1) JP5909238B2 (enExample)
KR (1) KR101836552B1 (enExample)
CN (1) CN103153947B (enExample)
CA (1) CA2813160C (enExample)
DK (1) DK2630120T3 (enExample)
ES (1) ES2692656T3 (enExample)
IL (1) IL225764A (enExample)
MX (1) MX2013004425A (enExample)
WO (1) WO2012052943A1 (enExample)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012052939A2 (en) 2010-10-20 2012-04-26 Actelion Pharmaceuticals Ltd Preparation of bicyclo[2.2.2]octan-2-one compounds
CN103570513A (zh) * 2012-08-07 2014-02-12 中国科学院大连化学物理研究所 一种手性双环[n.3.1]化合物的催化不对称合成方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009130679A1 (en) * 2008-04-25 2009-10-29 Actelion Pharmaceuticals Ltd Benzimidazole derivatives as calcium channel blockers
CN101668742A (zh) * 2007-04-27 2010-03-10 埃科特莱茵药品有限公司 桥联六员环化合物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2344461B1 (en) * 2008-10-22 2016-12-14 Actelion Pharmaceuticals Ltd. Salts of isobutyric acid (1r*,2r*,4r*)-2-(2-{[3-(4,7-dimethoxy-1 h-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester
WO2012052939A2 (en) 2010-10-20 2012-04-26 Actelion Pharmaceuticals Ltd Preparation of bicyclo[2.2.2]octan-2-one compounds

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101668742A (zh) * 2007-04-27 2010-03-10 埃科特莱茵药品有限公司 桥联六员环化合物
WO2009130679A1 (en) * 2008-04-25 2009-10-29 Actelion Pharmaceuticals Ltd Benzimidazole derivatives as calcium channel blockers

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
A Versatile Synthesis of Bicyclo[2.2.2]octan-2-one Derivatives;Philip Schmoldt and Jochen Mattay;《Synthesis》;20030520;第2003卷(第7期);1071-1078页 *
Multicomponent asymmetric reactions mediated by proline lithium salt;Polyssena Renzi等;《Organic & Biomolecular Chemistry》;20100113;第8卷(第5期);980-983页 *
Synergic asymmetric organocatalysis (SAOc) of Cinchona alkaloids and secondary amines in the synthesis of bicyclo[2.2.2]octan-2-ones;Marco Bella等;《Chem. Commun.》;20081208(第5期);597-599页 *

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Publication number Publication date
US20130289295A1 (en) 2013-10-31
CA2813160C (en) 2018-01-02
CN103153947A (zh) 2013-06-12
JP5909238B2 (ja) 2016-04-26
MX2013004425A (es) 2013-07-17
KR101836552B1 (ko) 2018-03-08
ES2692656T3 (es) 2018-12-04
DK2630120T3 (en) 2018-10-08
JP2013543841A (ja) 2013-12-09
WO2012052943A1 (en) 2012-04-26
EP2630120B1 (en) 2018-07-25
CA2813160A1 (en) 2012-04-26
US8816118B2 (en) 2014-08-26
KR20130126618A (ko) 2013-11-20
EP2630120A1 (en) 2013-08-28
IL225764A (en) 2016-11-30
IL225764A0 (en) 2013-06-27

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Granted publication date: 20151125