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Title:
環外二重結合を含むピラン誘導体
Document Type and Number:
Japanese Patent JP4884656
Kind Code:
B2
Abstract:
Pyran compounds having exocyclic double bonds are new. Pyran compounds of formula (I) having exocyclic double bonds are new. [Image] a-e : 0 or 1; W : -CH 2- or -C(=O)-; R 11>H, 1-15 C alkyl optionally substituted by halo or CN and optionally having at least one CH 2group replaced by -Ctriple boundC-, -CH=CH-, -O-, -S-, or -C(O)-O- such that heteroatoms are not directly bonded to each other; R 1>2>H, halo, -CN, -NCS, -O-aralkyl or 1-15 C alkyl optionally substituted by halo or CN and optionally having at least one CH 2group replaced by -Ctriple boundC-, -CH=CH-, -O-, -S-, or -C(O)-O- such that heteroatoms are not directly bonded to each other; Z 1>1>single bond, -CH 2-, -CH 2CH 2, -CF 2CH 2, -CH 2CF 2-, -CF 2CF 2-, -CH=CH- or -Ctriple boundC-; Z 1>2>-CH 2-, -CH 2CH 2-, -CF 2CH 2-, -CH 2CF 2- or -CF 2CF 2-; Z 1>3>-Z 1>5>a single bond, -CH 2CH 2-, -CF 2CH 2-, -CH 2CF 2-, -CF 2CF 2-, -CH=CH-, -Ctriple boundC- -CH 2O-, -CF 2O- or -C(O)- or -C(O)-O-; A 11>, A 12>1,4-cyclohexylene or 1,3-dioxane-5,2-diyl; A 13>, A 14>1,3-cyclobutylene, 3,3'-spiro(cyclobutane-1,1'-cyclobutane), 1,4-cyclohexylene, optionally fluorinated 1,4-phenylene, optionally fluorinated tetralin-6,2-diyl or optionally fluorinated naphthalene-2,6-diyl; A 15>as A 13>; or A 15>-R 12>4-hydroxyphenyl (optionally fluorinated), cyclobutanone-3-yl, cyclohexanone-4-yl or a group of formula (i); [Image] R 13>,R 1>4>1-7C alkyl or together form a 2-7C alkylene bridge; or Z 13>[A 13>Z 14>] c[A 14>Z 15>] d[A 15>] eR 12>a group of formula (ii) or (iii); [Image] L 1>7>-L 1>9>H or F. With the provisos that when Z 13>and R 1>2>are directly bonded R 1>2>is aralkyl, alkyl or alkenyl, if Z 1>3>is -C(=O)-O- or -C(=O)- and Z 1>3>is not -CH 2O or -CF 2O-, when Z 1>4>is -C(=O)-O- or -C(=O)- and Z 1>4>is not -CH 2O or -CF 2O-, when Z 1>5>and R 1>2>are directly bonded, R 1>2>= is aralkyl, alkyl or alkenyl when Z 1>5>is -C(=O)-O- or -C(=O)- and Z 1>5>is not -CH 2O- or -CF 2O-. Independent claims are included for: (1) a process for the production of the pyran compound (I) comprising a metathesis reaction of an ethyne compound of formula (II) in the presence of a metathesis catalyst; (2) ethyne compounds of formula (II); and (3) hydroxy alkene compounds of formula (III) [Image] [Image].

Inventors:
Aike porch
Volker Mayer
Werner Binder
Michael Heckmeier
Georg Ruessem
Stephan Gartler
Application Number:
JP2004157039A
Publication Date:
February 29, 2012
Filing Date:
May 27, 2004
Export Citation:
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Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung
International Classes:
C07D309/04; C07D309/20; C07B53/00; C07B61/00; C07C33/48; C07C43/176; C07C69/76; C07C69/773; C07D309/06; C07D309/08; C07D309/22; C07D309/28; C09K19/34
Domestic Patent References:
JP2001316383A
JP2002537297A
JP2001072626A
JP6211865A
JP59164788A
JP2002128776A
JP2002193853A
JP1503387A
JP2002180050A
JP2000053602A
JP11349582A
JP6025210A
JP3261779A
Foreign References:
DE19640618A1
Other References:
MORI,M. et al,Remarkable effect of ethylene gas in the intramolecular enyne metathesis of terminal alkynes,Journal of Organic Chemistry,1998年,Vol.63, No.18,pp.6082-6083
RENAUD,J. et al,Novel Synthesis of Cyclic Alkenylboronates via Ring-Closing Metathesis,Journal of the American Chemical Society,1998年,Vol.120, No.31,pp.7995-7996
FU,G.C. et al,The application of catalytic ring-closing olefin metathesis to the synthesis of unsaturated oxygen heterocycles,Journal of the American Chemical Society,1992年,Vol.114, No.13,pp.5426-5427
CARDA,M. et al,Stereoselective synthesis of (-)-malyngolide, (+)-malyngolide and (+)-tanikolide using ring-closing metathesis,Tetrahedron,2003年 2月,Vol.59, No.6,pp.857-864
FUERSTNER,A. et al,Ruthenium Carbene Complexes with N,N'-Bis(mesityl)imidazol-2-ylidene Ligands: RCM Catalysts of Extended Scope,Journal of Organic Chemistry,2000年,Vol.65, No.7,pp.2204-2207
Attorney, Agent or Firm:
Kiyoji Kuzuwa



 
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