58359-50-5

Basic information

• Product Name: Phenylphosphonous acid bis[(1R,2S,5R)-5β-methyl-2α-(1-methylethyl)cyclohexyl] ester
• Synonyms: Phenylphosphonous acid bis[(1R,2S,5R)-5β-methyl-2α-(1-methylethyl)cyclohexyl] ester
• CAS NO: 58359-50-5
• Molecular Formula: C₂₆H₄₃O₂P
• Molecular Weight: 418.592181
• Mol File: 58359-50-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Phenylphosphonous acid bis[(1R,2S,5R)-5β-methyl-2α-(1-methylethyl)cyclohexyl] ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylphosphonous acid bis[(1R,2S,5R)-5β-methyl-2α-(1-methylethyl)cyclohexyl] ester(58359-50-5)
• EPA Substance Registry System: Phenylphosphonous acid bis[(1R,2S,5R)-5β-methyl-2α-(1-methylethyl)cyclohexyl] ester(58359-50-5)

Safety Data

• Hazardous Substances Data: 58359-50-5(Hazardous Substances Data)

Upstream product

• 2216-51-5 (-)-menthol 
• 644-97-3 Dichlorophenylphosphine 

Downstream Products

• 105499-75-0 phenyl-isopropyl-O-menthylphosphinit 
• 1605-53-4 diethyl-phenyl-phosphine 
• 207605-95-6 [(SP,1R,2S,5R)-(-)-menthyl-O]tert-butyl-phenylphosphinite 
• 29949-75-5 diallyl-phenyl-phosphane 
• 6372-43-6 diisopropylphenylphosphane 

Relevant articles and documents

Asymmetric hydrovinylation of styrene applying cationic allyl palladium complexes of a P-chiral ligand Prof. Dr. Dr. hc Friedrich Asinger on the occasion of his 90th birthday

Cationic allyl palladium complexes of the diasteriomerically pure P-chiral ligand tert-butyl(menthyl-O)phenylphosphinite 1 were prepared from [(η3-C3H5)PdI]2 and [(η3-C3H5)Pd(cod)]X. Ligand 1 and the complex [(η3-C3H5)PdI(1)] 9 were characterized by X-ray crystallography. The absolute configuration at the phosphorus center of 1 was determined to be (S) for the (-)-menthol derivative. Crystals are orthorombic, space group P212121, a=8.505(3) A, b=10.82(1) A, c=23.297(3) A, V=2144(2) A3. Complex 9 shows distorted square planar geometry. Crystals are trigonal, space group P32, a=13.980(5) A, c=11.292(3) A, V=1911(2) A3. Asymmetric codimerization of styrene and ethylene was successfully applied. High enantioselectivities of up to 86% ee have been obtained at room temperature. The codimer 3-phenylbut-1-ene (3PB1) was formed in high selectivity (up to 96%) with only small amounts of the isomerization products E- and Z-2-phenylbut-2-ene. By addition of various coordinating solvents, the catalyst system was efficiently stabilized. Variation of the complex counter anion had significant effect on enantioselectivity.

Nonracemic menthyl phosphorylacetates

Phosphorylacetic acid esters containing the menthoxy fragment at the phosphorus atom or at the carbonyl group were synthesized. The configurations of the enantiomerically pure compounds, viz., methyl (ethoxy)(menthyloxy) phosphorylacetate and menthyl [(2-

OPTISCH AKTIVE PHOSPHINE DURCH ASYMMETRISCHE SUBSTITUTION PROCHIRALER, HOMOCHIRAL SUBSTITUIERTER PHOSPHONITE

Phenylphosphonous acid dimenthylester and its dibornylester react with bulky nucleophiles to give diastereomeric phosphinous acid esters.The asymmetric induction is as high as 95 percent d.e.If reaction conditions favouring inversion at phosphorus are used then the (R)-menthoxy group of the prochiral starting material is substituted.The phosphinous acid ester can be converted, with partial racemization, into optically active Horner-phosphines.