91228-92-1

Basic information

• Product Name: Ethanone, 1-(2-methylcyclopropyl)-2-(triphenylphosphoranylidene)-, trans-
• CAS NO: 91228-92-1
• Molecular Formula: C24H23OP
• Molecular Weight: 358.42
• Mol File: 91228-92-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-(2-methylcyclopropyl)-2-(triphenylphosphoranylidene)-, trans-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(2-methylcyclopropyl)-2-(triphenylphosphoranylidene)-, trans-(91228-92-1)
• EPA Substance Registry System: Ethanone, 1-(2-methylcyclopropyl)-2-(triphenylphosphoranylidene)-, trans-(91228-92-1)

Safety Data

• Hazardous Substances Data: 91228-92-1(Hazardous Substances Data)

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 42274-66-8 trans-2-methylcyclopropanecarboxylic acid chloride 

Downstream Products

• 91279-29-7 Toluene-4-sulfonic acid (2R,5R)-5-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-((1S,2S)-2-methyl-cyclopropyl)-hexyl ester 
• 91229-00-4 Toluene-4-sulfonic acid (2R,5R)-5-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-((1R,2R)-2-methyl-cyclopropyl)-hexyl ester 
• 91279-28-6 Toluene-4-sulfonic acid (2S,5R)-5-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-((1S,2S)-2-methyl-cyclopropyl)-hexyl ester 
• 91279-89-9 Toluene-4-sulfonic acid (2S,5R)-5-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-((1R,2R)-2-methyl-cyclopropyl)-hexyl ester 
• 91229-02-6 C₃₇H₅₄⁽²⁾H₂O₄S 
• 67314-15-2 (24R,25R,26R)-petrosterol 

Relevant articles and documents

Stereochmical Effects in Cyclopropane Ring Openings: Synthesis and Isomerization of Petrosterol and All Three of Its Trans Cyclopropane Diastereomers

All four trans isomers of the marine sterol petrosterol, with a side chain terminating in a cyclopropane ring, have been synthesized.The absolute stereochemistry of the diastereomers was determined by correlation with compounds of known absolute stereochemistry.The product distribution resulting from the acid-catalyzed isomerization of these four diastereomers shows a marked dependence on the relative stereochemistry between the cyclopropane ring and the adjacent chiral center at C24.A careful examination of the conformations available to the side chain leads to a rational explanation of this dependence, and sheds light on hitherto unrecognized subtle stereochemical features operating among aliphatic cyclopropanes.In addition we report the synthesis and acid-catalyzed ring opening of (24S,25S,26S)-22,22-dideuteriopetrosterol and the confirmation by this labeling study that one of the products of the isomerization reaction arises via a 1,5-hydride-shift mechanism.