134785-23-2

Basic information

• Product Name: (+/-)-cis-1-carbomethoxy-2-bromomethyl-4-cyclohexene
• CAS NO: 134785-23-2
• Molecular Weight: 233.105
• Mol File: 134785-23-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+/-)-cis-1-carbomethoxy-2-bromomethyl-4-cyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-cis-1-carbomethoxy-2-bromomethyl-4-cyclohexene(134785-23-2)
• EPA Substance Registry System: (+/-)-cis-1-carbomethoxy-2-bromomethyl-4-cyclohexene(134785-23-2)

Safety Data

• Hazardous Substances Data: 134785-23-2(Hazardous Substances Data)

Upstream product

• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 67-56-1 methanol 
• 2744-05-0 8-oxabicyclo[4.3.0]non-3-en-9-one 

Downstream Products

• 134877-10-4 (+/-)-cis-1-carbomethoxy-2-bromomethylcyclohexane 
• 134877-09-1 (+)-cis-1-carbomethoxy-2-methyl-4-cyclohexene 
• 134877-08-0 (-)-cis-1-carbomethoxy-2-methylcyclohexane 
• 7605-54-1 methyl (1S*,2R*)-2-methylcyclohexanecarboxylate 
• 102629-35-6 (1R,6S)-6-Methyl-3-cyclohexene-1-carboxylic Acid 
• 20993-77-5 (+)-(1R,2S)-1-carboxy-2-methylcyclohexane 
• 65376-02-5 (1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one 
• 134877-11-5 (+)-(1S,2R)-1-carbomethoxy-2-bromomethyl-4-cyclohexene 
• 133806-73-2 (+/-)-cis-1-carbomethoxy-2-bromomethylcyclohexane 
• 15111-54-3 (+/-)-cis-1-carbomethoxy-2-methyl-4-cyclohexene 
• 88586-06-5 (3aS,7aR)-3a,4,7,7a-tetrahydroisobenzofuran-1(3H)-one 

Relevant articles and documents

Enzymes in organic synthesis 49. Resolutions of racemic monocyclic esters with pig liver esterase

Pig liver esterase (PLE)- catalyzed hydrolyses of the racemic methyl esters of cyclobutane-, cyclohexane-, and cyclohex-4-ene-carboxylic acids bearing cis-2-methyl or cis-2-bromomethyl substituents are highly stereoselective, giving the corresponding acid products of ≥ 97% ee. The stereoselectivity of the enzyme exhibits the expected reversal for such compounds, with the absolute configurations of the cyclobutane and cyclohexame acids being of the opposite absolute configuration type, and cyclopentane substrates such as cis-1-carbomethoxy-2-methylcyclopentane representing the change-over structures and giving products of only 22%ee. This stereoselectivtiy reversal, and the absolute configurations preferred, are as predicted by the recently proposed active site model for the enzyme.