139492-31-2

Basic information

• Product Name: (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane
• Synonyms: (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane
• CAS NO: 139492-31-2
• Molecular Weight: 148.205
• Mol File: 139492-31-2.mol
• Article Data: 29

Chemical Properties

• CAS DataBase Reference: (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane(139492-31-2)
• EPA Substance Registry System: (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane(139492-31-2)

Safety Data

• Hazardous Substances Data: 139492-31-2(Hazardous Substances Data)

Upstream product

• 75-11-6 diiodomethane 
• 167612-64-8 1,2-O-Isopropylidene-3-O-benzyl-4,5-O-<(1'R)-cis-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 100-42-5 styrene 
• 63254-50-2 L-menthyl diazoacetate 
• 65437-23-2 d-menthyl diazoacetate 
• 139021-83-3 1-isopropyl-2-methylpropyl diazoacetate 
• 936-98-1 rac-((1S,2R)-2-phenylcyclopropyl)methanol 
• 94112-37-5 t-butyl 2-phenylcyclopropane-1-carboxylate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 946-38-3 cis-1-ethoxycarbonyl-2-phenylcyclopropane 
• 908094-04-2 phenyldiazomethane 
• 107-18-6 allyl alcohol 
• 100-52-7 benzaldehyde 

Downstream Products

• 34271-30-2 rac-(1S,2R)-2-phenylcyclopropanecarbaldehyde 
• 167612-65-9 (1R,2S)-1-formyl-2-phenylcyclopropane 
• 186183-64-2 (1S,2R)-1-formyl-2-phenylcyclopropane 
• 29667-46-7 (1S,2R)-2-phenylcyclopropylmethanol 
• 48126-51-8 (1R,2S)-2-phenylcyclopropane-1-carboxylic acid 
• 1426228-50-3 cis-N-(2-bromophenyl)-N-methyl-2-phenylcyclopropanecarboxamide 
• 1426228-31-0 (1R,2R)-1'-methyl-2-phenylspiro[cyclopropane-1,3'-indolin]-2'-one 
• 22467-91-0 ethyl (E)-3-(cis-(1R,2R)-2-phenylcyclopropyl)propenoate 
• 22467-91-0 cis-1-(trans-β-Ethoxycarbonylvinyl)-2-phenylcyclopropan 
• 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

Enantioselective Cyclopropanation of Allylic Alcohols Catalyzed by a Chiral Disulfonamide-Aluminum Complex

A chiral disulfonamide-alkylaluminum complex prepared from (1R,2R)-N,N'-bis(benzenesulfonyl)-1,2-cyclohexanediamine and trialkylaluminum or i-Bu2AlH has been found to catalyze a Simmons-Smith cyclopropanation of allylic alcohols with Et2Zn and CH2I2 to afford the corresponding cyclopropanes in excellent yields with high enantiomeric excesses.

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.

Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2- b]pyridazines

In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor-acceptor cyclopropanes to furnish hexahydropyrrolo[1,2-b]pyridazines. We also performed these two steps in one pot in a consecutive manner. In addition, a monodecarboxylation reaction of hexahydropyrrolo[1,2-b]pyridazine was achieved with a good yield.