149030-24-0

Basic information

• Product Name: Cyclopropanemethanol, 2,2-diphenyl-, (R)-
• CAS NO: 149030-24-0
• Molecular Formula: C16H16O
• Molecular Weight: 224.302
• Mol File: 149030-24-0.mol

Chemical Properties

• CAS DataBase Reference: Cyclopropanemethanol, 2,2-diphenyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanemethanol, 2,2-diphenyl-, (R)-(149030-24-0)
• EPA Substance Registry System: Cyclopropanemethanol, 2,2-diphenyl-, (R)-(149030-24-0)

Safety Data

• Hazardous Substances Data: 149030-24-0(Hazardous Substances Data)

Upstream product

• 530-48-3 1,1-Diphenylethylene 
• 65437-23-2 d-menthyl diazoacetate 
• 75-11-6 diiodomethane 
• 4801-14-3 3,3-diphenylprop-2-en-1-ol 
• 926905-41-1 2,2-diphenylcyclopropane-1-carbaldehyde 
• 1196891-51-6 C₂₃H₁₈N₂O₆ 
• 53692-74-3 (R)-2,2-diphenylcyclopropanecarboxylic acid 

Downstream Products

• 926905-41-1 2,2-diphenylcyclopropane-1-carbaldehyde 
• 53692-74-3 (R)-2,2-diphenylcyclopropanecarboxylic acid 
• 926905-44-4 N-(2-aminoethyl)-2,2-diphenylcyclopropane-carboxamide 
• 103419-18-7 [14C]-(+)-Cibenzoline 

Relevant articles and documents

Convenient preparation of optically active cibenzoline and analogues from 3,3-diaryl-2-propen-1-ols

(R)-(+)-Cibenzoline (95% ee) was synthesized in two steps from (+)-2,2-diphenylcyclopropylmethanol 3a (98% ee), which was oxidized with IBX in DMSO, followed by treatment with ethylenediamine in the presence of I2 and K2CO3/sub

The use of 1,2-O-isopropylidene-α-d-xylofuranose as a chiral auxiliary in asymmetric cyclopropanation reactions

The stereoselective synthesis of cyclopropylmethylidene acetals derived from 1,2-O-isopropylidene-d-xylofuranose, as a chiral auxiliary, is described. The Simmons-Smith cyclopropanation reaction of the corresponding alkenylidene derivatives with CH2

Catalytic enantioselective cyclopropanation of allylic alcohols using recyclable fluorous disulfonamide ligand

Cyclopropanation of allylic alcohols with Et2Zn and CH2I2 in the presence of a catalytic amount of fluorous disulfonamide 3 afforded the corresponding cyclopropylmethanols in 69-96% yield with 49-83% ee. The fluorous ligand 3 was readily recovered from the reaction mixture by the fluorous solid-phase extraction (FSPE) and could be reused without a significant loss of the catalytic activity and enantioselectivity.

Syntheses of (R)-(+)-cibenzoline and analogues via catalytic enantioselective cyclopropanation using (S)-phenylalanine-derived disulfonamide

Cyclopropanation of 3,3-diaryl-2-propen-1-ols 1 with Et2Zn and CH2I2 proceeded in the presence of a catalytic amount of (S)-2-(methanesulfonyl)amino-1-(p-toluenesulfonyl)amino-3-phenylpropane 2 to afford the corresponding

Highly Enantioselective Intermolecular Cyclopropanation Catalyzed by Dirhodium(II) Tetrakis[3(S)-phthalimido-2-piperidinonate]: Solvent Dependency of the Enantioselection

The enantioselectivity in cyclopropanations catalyzed by dirhodium(II) tetrakis[3(S)-phthalimido-2-piperidinonate] has been found to be substantially improved by employing ether as the rarely used solvent. Cyclopropanations of styrenes or 1,1-disubstituted alkenes with 2,4-dimethyl-3-pentyl diazoacetate in ether are promoted by this catalyst to afford the corresponding cyclopropane products in the highest levels of enantioselectivity (up to 98% ee) reported to date for the dirhodium(II)-catalyzed intermolecular cyclopropanation reactions.

Dirhodium(II)tetrakis[3(S)-phthalimido-2-piperidinonate]: A novel dirhodium(II) carboxamidate catalyst for asymmetric cyclopropanation

Dirhodium(II) tetrakis[3(S)-phthalimido-2-piperidinonate] catalyzes cyclopropanation of α-methylstyrene with d-menthyl diazoacetate to give d-menthyl (1S,2S)-2-methyl-2-phenylcyclopropanecarboxylate of 90% de.