77085-89-3

Basic information

• Product Name: (-)-(S_P)-<(menthoxycarbonyl)methyl>phenylvinylphosphine oxide
• Synonyms: (-)-(S_P)-<(menthoxycarbonyl)methyl>phenylvinylphosphine oxide
• CAS NO: 77085-89-3
• Molecular Weight: 348.422
• Mol File: 77085-89-3.mol

Chemical Properties

• CAS DataBase Reference: (-)-(S_P)-<(menthoxycarbonyl)methyl>phenylvinylphosphine oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(S_P)-<(menthoxycarbonyl)methyl>phenylvinylphosphine oxide(77085-89-3)
• EPA Substance Registry System: (-)-(S_P)-<(menthoxycarbonyl)methyl>phenylvinylphosphine oxide(77085-89-3)

Safety Data

• Hazardous Substances Data: 77085-89-3(Hazardous Substances Data)

Upstream product

• 77085-88-2 butoxy(phenyl)(vinyl)phosphine 
• 16832-20-5 (1R,2S,5R)-menthol bromoacetate 
• 16832-20-5 (-)-menthyl bromoacetate 

Downstream Products

• 134817-57-5 [(R)-((2R,3aR)-6,6-Dimethyl-hexahydro-pyrrolo[1,2-b]isoxazol-2-yl)-phenyl-phosphinoyl]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 134929-97-8 [(R)-((2S,3aS)-6,6-Dimethyl-hexahydro-pyrrolo[1,2-b]isoxazol-2-yl)-phenyl-phosphinoyl]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 89438-78-8 (-)-(S_P)-methylphenylvinylphosphine oxide 
• 119987-41-6 [(R)-(3-Methyl-butyl)-phenyl-phosphinoyl]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 122768-31-4 [(R)-(2-Dimethylamino-ethyl)-phenyl-phosphinoyl]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 123473-93-8 [(R)-(2-Benzylamino-ethyl)-phenyl-phosphinoyl]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 37775-94-3 (-)-(S_P)-Cyclohexylmethylphenylphosphine oxide 
• 26515-05-9 (-)-(S_P)-ethylmethylphenylphosphine oxide 
• 1515-99-7 (S)-(-)-Methylphenyl-n-propylphosphanoxid 
• 119987-35-8 n-hexylmethylphenylphosphine oxide 
• 89438-80-2 methyl(4-nonen-1-yl)phenylphosphine oxide 
• 77085-90-6 (-)-ethyl(menthoxycarbonylmethyl)phenylphosphine oxide 

Relevant articles and documents

Enantioselective catalysis, XVIII [1] the influence of non-coordinated stereocenters on the enantioselective hydrogenation

3,4-Bis{[2-(methyl-phenyl-oxophosphanyl)-ethyl]phenyl-phosphanyl} pyrrolidines have been synthesized by Michael Addition from the corresponding methyl-phenyl-vinyl-phosphane oxides and 3,4-bis(phenylphosphino)pyrrolidines. For purification of the ligands palladium complexes were used and with the enantiomerically pure ligands Rh complexes have been prepared. The catalyst has 6 stereogenic centers. In the hydrogenation of Z-α-acetamidocinnamic acid all six stereogenic centers have an influence on the enantioselectivity. The influence is strongest from the C stereocenters of the pyrrolidine ring. Less important are the stereogenic centers on the coordinated P atoms. The influence of the stereocenters on the non-coordinated P=O groups is the least, but it is not negligible. The ee values obtained with the ligands containing P=O groups are much lower than those obtained with ligands which are substituted only with aryl groups. Ketones are hydrogenated with only low ee's.

OPTICALLY ACTIVE PHOSPHINE OXIDES SYNTHESIS AND ABSOLUTE CONFIGURATION OF (MENTHOXYCARBONYLMETHYL)PHENYLVINYL PHOSPHINE OXIDE

The enantiomeric (-)-(menthoxycarbonylmethyl)phenylvinylphosphine oxide 1b has been prepared and its absolute configuration rigorously established via chemical correlation.One-step decarbalkoxylation of (-)-ethyl(methoxycarbonylmethyl)phenylphosphine oxid