196403-96-0

Basic information

• Product Name: (1S,2R)-2-phenyl-1-cyclopropanol
• Synonyms: (1S,2R)-2-phenyl-1-cyclopropanol
• CAS NO: 196403-96-0
• Molecular Weight: 134.178
• Mol File: 196403-96-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1S,2R)-2-phenyl-1-cyclopropanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-2-phenyl-1-cyclopropanol(196403-96-0)
• EPA Substance Registry System: (1S,2R)-2-phenyl-1-cyclopropanol(196403-96-0)

Safety Data

• Hazardous Substances Data: 196403-96-0(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 1083213-30-2 (1S,2R)-1-(benzyldimethylsilyl)-2-phenylcyclopropane 
• 108-05-4 vinyl acetate 
• 75-11-6 diiodomethane 

Relevant articles and documents

Synthesis of optically active boron-silicon bifunctional cyclopropane derivatives through enantioselective copper(I)-catalyzed reaction of allylic carbonates with a diboron derivative

(Chemical Equation Presented) Two for the show: A copper(I)-catalyzed reaction forms boron-silicon bifunctional cyclopropane derivatives from γ-silylated allylic carbonates and a diboron species (see scheme). The reaction is highly enantioselective when a chiral bisphosphine ligand is used. The stereoelectronic effect of the silyl group induces unusual regioselectivity of the boryl-copper(I) addition across the C-C double bond.

Chirality transfer from silicon to carbon via diastereoselective Simmons-Smith cyclopropanation of chiral alkenylsilanols

Simmons-Smith cyclopropanation of a chiral alkenylsilanol with CH2I2-Et2Zn proceeds diastereoselectively to give the corresponding cyclopropylsilanol product. Chirality transfer from silicon to the alkenyl carbons of the silicon substituent is observed. The stereochemistry of the obtained cyclopropylsilanol is confirmed by converting to cyclopropanol via Tamao oxidation.

Asymmetric Cyclopropanation of 1-Alkenylboronic Esters and Its Application to the Synthesis of Optically Active Cyclopropanols

The first asymmetric cyclopropanation of 1-alkenylboronic esters was realized by diastereofacial selective Simmons-Smith reaction of the esters modified by enantiomerically pure diols such as tetramethyltartaramide.Subsequent oxidation of the resulting cyclopropylboronates gave optically active 2-substituted cyclopropanols in 73-94percent ee.These reactive compounds possess high synthetic potential.