29667-46-7

Basic information

• Product Name: Cyclopropanemethanol, 2-phenyl-, (1S,2R)-
• Synonyms: cis-2-phenylcyclopropylmethanol;(+)-(1S,2R)-(2-phenylcyclopropyl)methanol;(+)-(1S,2R)-2-phenylcyclopropylmethanol;((1S,2R)-2-Phenyl-cyclopropyl)-methanol;(-)-(1R,2S)-2-phenylcyclopropylmethanol
• CAS NO: 29667-46-7
• Molecular Formula: C10H12O
• Molecular Weight: 148.205
• Mol File: 29667-46-7.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 73 - 76 °C (0.1 mmHg)
• Density: 1.089±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Cyclopropanemethanol, 2-phenyl-, (1S,2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanemethanol, 2-phenyl-, (1S,2R)-(29667-46-7)
• EPA Substance Registry System: Cyclopropanemethanol, 2-phenyl-, (1S,2R)-(29667-46-7)

Safety Data

• Hazardous Substances Data: 29667-46-7(Hazardous Substances Data)

Upstream product

• 5682-61-1 (1S,2R)-2-phenylcyclopropanecarboxylic acid methyl ester 
• 20030-70-0 methyl 2-phenylcyclopropane-1-carboxylate 
• 100-42-5 styrene 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 100-52-7 benzaldehyde 
• 75-11-6 diiodomethane 
• 104-54-1 3-Phenylpropenol 
• 908094-04-2 phenyldiazomethane 
• 107-18-6 allyl alcohol 
• 939-89-9 (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 946-38-3 cis-1-ethoxycarbonyl-2-phenylcyclopropane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 67528-62-5 cis-methyl 2-phenylcyclopropane-1-carboxylate 

Downstream Products

• 186183-64-2 (1S,2R)-1-formyl-2-phenylcyclopropane 
• 139492-31-2 (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane 
• 167612-65-9 (1R,2S)-1-formyl-2-phenylcyclopropane 
• 23020-18-0 (1S,2R)-2-phenylcyclopropanecarboxylic acid 
• 1402883-29-7 ethyl 3-oxo-3-((1S,2R)-2-phenylcyclopropyl)propanoate 
• 1402883-30-0 2-amino-6-((1S,2R)-2-phenylcyclopropyl)pyrimidin-4(3H)-one 
• 1402883-27-5 2-amino-3-methyl-6-((1S,2R)-2-phenylcyclopropyl)pyrimidin-4(3H)-one 
• 110659-52-4 (1'R,2'S)-1-(2'-methylcyclopropyl)-2-nitrobenzene 
• 110659-53-5 (+)-(1'R,2'S)-2-(2'-methylcyclopropyl)aniline 
• 29667-47-8 (+)-(1S,2R)-1-methyl-2-phenylcyclopropane 
• 22467-91-0 cis-1-(trans-β-Ethoxycarbonylvinyl)-2-phenylcyclopropan 
• 17955-08-7 cis-2-Phenyl-vinyl-cyclopropan 
• 625389-83-5 (1R,2S)-1-[4-(2,4-dimethylphenyl)piperazyl]carbonyl-2-phenylcyclopropane 
• 307952-37-0 [4-(2,4-Dimethyl-phenyl)-piperazin-1-yl]-((1S,2S)-2-phenyl-cyclopropyl)-methanone 

Relevant articles and documents

Donor-Acceptor Bicyclopropyls as 1,6-Zwitterionic Intermediates: Synthesis and Reactions with 4-Phenyl-1,2,4-triazoline-3,5-dione and Terminal Acetylenes

The bicyclopropyl system activated by incorporation of donor and acceptor groups in the presence of Lewis acids was used as a synthetic equivalent of 1,6-zwitterions. Opening of both cyclopropane rings in 2′-aryl-1,1′-bicyclopropyl-2,2-dicarboxylates (D-A bicyclopropyl, ABCDs) in the presence of GaI3 + Bu4N+GaI4- results in 5-iodo-5-arylpent-2-enylmalonates as products of HI formal 1,6-addition to the bicyclopropyl system. The use of GaCl3 or GaBr3 as a Lewis acid and terminal aryl or alkyl acetylenes as 1,6-zwitterion interceptors allows the alkyl substituent to be grown to give the corresponding acyclic 7-chloro(bromo)-hepta-2,6-dienylmalonates. The reaction of ABCDs with 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) catalyzed by Yb(OTf)3 also results in the opening of both cyclopropane rings. The reaction products are tetrahydropyridazine derivatives - (7,9-dioxo-1,6,8-triazabicyclo[4.3.0]non-3-en-2-ylmethyl)malonates - containing one more PTAD moiety in the malonyl group.

Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases

Ene reductases from the Old Yellow Enzyme (OYE) family reduce the C=C double bond in α,β-unsaturated compounds bearing an electron-withdrawing group, for example, a carbonyl group. This asymmetric reduction has been exploited for biocatalysis. Going beyond its canonical function, we show that members of this enzyme family can also catalyze the formation of C?C bonds. α,β-Unsaturated aldehydes and ketones containing an additional electrophilic group undergo reductive cyclization. Mechanistically, the two-electron-reduced enzyme cofactor FMN delivers a hydride to generate an enolate intermediate, which reacts with the internal electrophile. Single-site replacement of a crucial Tyr residue with a non-protic Phe or Trp favored the cyclization over the natural reduction reaction. The new transformation enabled the enantioselective synthesis of chiral cyclopropanes in up to >99 % ee.

Copper-catalyzed regio- and stereoselective intermolecular three-component oxyarylation of allenes

A copper(II)-catalyzed intermolecular three-component oxyarylation of allenes using arylboronic acids as a carbon source and TEMPO as an oxygen source is described. The reaction proceeded under mild conditions with high regio- and stereoselectivity and functional group tolerance. A plausible reaction mechanism is proposed, involving carbocupration of allenes, homolysis of the intervening allylcopper(II), and a radical TEMPO trap.