75351-30-3

Basic information

• Product Name: Cyclohexanecarboxylic acid, 2-ethenyl-6-oxo-, methyl ester
• CAS NO: 75351-30-3
• Molecular Formula: C10H14O3
• Molecular Weight: 182.219
• Mol File: 75351-30-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Cyclohexanecarboxylic acid, 2-ethenyl-6-oxo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxylic acid, 2-ethenyl-6-oxo-, methyl ester(75351-30-3)
• EPA Substance Registry System: Cyclohexanecarboxylic acid, 2-ethenyl-6-oxo-, methyl ester(75351-30-3)

Safety Data

• Hazardous Substances Data: 75351-30-3(Hazardous Substances Data)

Upstream product

• 930-68-7 cyclohexenone 
• 1826-67-1 vinyl magnesium bromide 
• 79-22-1 methyl chloroformate 
• 132738-78-4 2-[((E)-Octa-2,7-dienyl)oxy]-tetrahydro-pyran 
• 83670-61-5 (E)-9-Hydroxy-3-oxo-non-7-enoic acid methyl ester 
• 62179-18-4 (2E)-octa-2,7-dien-1-ol 
• 68231-79-8 (E)-8-(Tetrahydro-pyran-2-yloxy)-oct-6-en-2-one 
• 82259-88-9 methyl (E)-3-oxo-9-phenoxy-7-nonenoate 
• 344880-67-7 methyl (E)-3-oxo-9-(methoxycarbonyl)oxy-7-nonenoate 

Downstream Products

• 64847-85-4 3-ethyl cyclohexanone 
• 1740-63-2 3-vinylcyclohexanone 

Relevant articles and documents

Total Synthesis of (?)-Glaucocalyxin A

A practically useful method for the formation of the highly oxygenated bicyclo[3.2.1]octane ring system through Mn(OAc)3-mediated radical cyclization of alkynyl ketones was developed, which opens up a new avenue for the total synthesis of a number of highly oxidized diterpenoids. Application of this method enabled the first total synthesis of (?)-glaucocalyxin A. Other salient features of the synthesis include a highly enantioselective conjugate addition/acylation cascade reaction, a Yamamoto aldol reaction, and an intramolecular Diels–Alder reaction to assemble the A/B ring system.

COMPLETE RETENTION OF CHIRALITY IN THE PALLADIUM CATALYZED CYCLIZATION OF METHYL (R)-3-OXO-7-METHOXYCARBONYLOXY)-8-NONENOATE

Optically active methyl (R)-3-oxo-7-methoxycarbonyloxy)-8-nonenoate (1) underwent intramolecular allylation catalyzed by Pd(OAc)2-dppe in THF at room temperature to give racemic 3-vinyl-2-methoxy-carbonylcyclohexanone (3), whereas similar palladium-cataly

PREPARATION OF FIVE- AND SIX- MEMBERED CYCLIC KETONES BY THE PALLADIUM-CATALYZED CYCLIZATION REACTION. APPLICATION TO METHYL DIHYDROJASMONATE SYNTHESIS

Methyl 3-oxo-8-phenoxy-6-octenoate (1) was cyclized using Pd(OAc)2-PPh3 as a catalyst to give 2-carbomethoxy-3-vinylcyclopentanone (2) and 2-carbomethoxy-4-cycloheptenone (3).The former was the main product in acetonitrile. 2-Alkylated 3-oxo-8-phenoxy-6-octenoates were converted mainly to the five-membered ketones.Based on this cyclization method, methyl dihydrojasmonate (8) was prepared from methyl 2-pentyl-3-oxo-8-phenoxy-6-octenoate (5).Methyl 3-oxo-9-phenoxy-7-nonenoate (10) was subjected to the palladium-catalysed cyclization to afford 2-carbomethoxy-3-vinylcyclohexanone (11) selectively without forming the eight membered ketone (12).