264614-04-2

Basic information

• Product Name: Cyclobutanecarboxylic acid, 2-ethenyl-, ethyl ester, (1S,2R)- (9CI)
• Synonyms: Cyclobutanecarboxylic acid, 2-ethenyl-, ethyl ester, (1S,2R)- (9CI)
• CAS NO: 264614-04-2
• Molecular Formula: C9H14O2
• Molecular Weight: 154.20626
• Product Categories: CARBOXYLICESTER
• Mol File: 264614-04-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 180.7±29.0 °C(Predicted)
• Appearance: /
• Density: 1.056±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Cyclobutanecarboxylic acid, 2-ethenyl-, ethyl ester, (1S,2R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclobutanecarboxylic acid, 2-ethenyl-, ethyl ester, (1S,2R)- (9CI)(264614-04-2)
• EPA Substance Registry System: Cyclobutanecarboxylic acid, 2-ethenyl-, ethyl ester, (1S,2R)- (9CI)(264614-04-2)

Safety Data

• Hazardous Substances Data: 264614-04-2(Hazardous Substances Data)

Upstream product

• 132640-86-9 ethyl (E)-5-bromo-2-pentenoate 
• 264613-90-3 ethyl (R_S,1S,2S)-2-[(1R)-1-(p-tolylsulfinyl)-2-(trimethylsilyl)ethyl]cyclobutanecarboxylate 

Relevant articles and documents

Extremely Efficient Chiral Induction in Conjugate Additions of p-Tolyl α-Lithio-β-(trimethylsilyl)ethyl Sulfoxide and Subsequent Electrophilic Trapping Reactions

Reaction of p-tolyl α-lithio-β-(trimethylsilyl)ethyl sulfoxide with α,β-unsaturated esters gave the conjugate addition products as a single diastereomer. The intermediate enolates were subsequently trapped with various alkyl halides or aldehydes to give the products with extremely high stereoselectivity. The reaction with α,β-unsaturated ketones also proceeded with high diastereoselectivity. Protolysis of the enolates derived from the α-methyl-α,β-unsaturated esters gave the products with high stereoselectivity. The stereo- and regioselective elimination of the sulfinyl group gave chiral homoallylic carboxylates.