138964-33-7

Basic information

• Product Name: 2-Propenoic acid, 3-phenyl-, cyclohexyl ester, (Z)-
• CAS NO: 138964-33-7
• Molecular Formula: C15H18O2
• Molecular Weight: 230.307
• Mol File: 138964-33-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-phenyl-, cyclohexyl ester, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-phenyl-, cyclohexyl ester, (Z)-(138964-33-7)
• EPA Substance Registry System: 2-Propenoic acid, 3-phenyl-, cyclohexyl ester, (Z)-(138964-33-7)

Safety Data

• Hazardous Substances Data: 138964-33-7(Hazardous Substances Data)

Upstream product

• 7779-17-1 (E)-cyclohexyl cinnamate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 102-92-1 Cinnamoyl chloride 
• 63254-54-6 cyclohexyl diazoacetate 
• 100-52-7 benzaldehyde 
• 108-93-0 cyclohexanol 
• 637-44-5 phenylpropyolic acid 
• 138964-26-8 cyclohexyl (2R*,3S*)-2-(tert-butyldimethylsilyl)-3-hydroxy-3-phenylpropionate 

Relevant articles and documents

MYOGLOBIN-BASED CATALYSTS FOR CARBENE TRANSFER REACTIONS

Methods are provided for carrying out carbene transfer transformations such as olefin cyclopropanation reactions, carbene heteroatom-H insertion reactions (heteroatom = N, S, Si), sigmatropic rearrangement reactions, and aldehyde olefination reactions with high efficiency and selectivity by using a novel class of myoglobin-based biocatalysts. These methods are useful for the synthesis of a variety of organic compounds which contain one or more new carbon-carbon or carbon-heteroatom (N, S, or Si) bond. The methods can be applied for conducting these transformations in vitro (i.e., using the biocatalyst in isolated form) and in vivo (i.e., using the biocatalyst in a whole cell system).

Myoglobin-catalyzed olefination of aldehydes

The olefination of aldehydes constitutes a most valuable and widely adopted strategy for constructing carbon-carbon double bonds in organic chemistry. While various synthetic methods have been made available for this purpose, no biocatalysts are known to mediate this transformation. Reported herein is that engineered myoglobin variants can catalyze the olefination of aldehydes in the presence of α-diazoesters with high catalytic efficiency (up to 4,900 turnovers) and excellent Ediastereoselectivity (92-99.9 % de). This transformation could be applied to the olefination of a variety of substituted benzaldehydes and heteroaromatic aldehydes, also in combination with different alkyl α-diazoacetate reagents. This work provides a first example of biocatalytic aldehyde olefination and extends the spectrum of synthetically valuable chemical transformations accessible using metalloprotein-based catalysts.