154460-15-8

Basic information

• Product Name: Phosphonic acid, [(1S,2E)-1-hydroxy-3-phenyl-2-propenyl]-, dimethyl ester
• CAS NO: 154460-15-8
• Molecular Formula: C11H15O4P
• Molecular Weight: 242.211
• Mol File: 154460-15-8.mol

Chemical Properties

• CAS DataBase Reference: Phosphonic acid, [(1S,2E)-1-hydroxy-3-phenyl-2-propenyl]-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, [(1S,2E)-1-hydroxy-3-phenyl-2-propenyl]-, dimethyl ester(154460-15-8)
• EPA Substance Registry System: Phosphonic acid, [(1S,2E)-1-hydroxy-3-phenyl-2-propenyl]-, dimethyl ester(154460-15-8)

Safety Data

• Hazardous Substances Data: 154460-15-8(Hazardous Substances Data)

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 868-85-9 Dimethyl phosphite 
• 186581-53-3 diazomethane 
• 104-55-2 3-phenyl-propenal 
• 96-36-6 methyl phosphite 
• 149794-31-0 dimethyl [(E)-1-hydroxy-3-phenyl-2-propenyl]phosphonate 

Relevant articles and documents

Synthesis of an optically active C1-symmetric Al(salalen) complex and its application to the catalytic hydrophosphonylation of aldehydes

(Chemical Equation Presented) Quite universally: The chiral trigonal-bipyramidal Al(salalen) complex 1 was synthesized and found to be an efficient catalyst for enantioselective hydrophosphonylation of various aldehydes with dimethyl phosphite (see scheme

Enantioselective hydrophosphonylation of aldehydes using an aluminum binaphthyl Schiff base complex as a catalyst

An aluminum binaphthyl Schiff base complex was found to be an efficient catalyst for enantioselective hydrophosphonylation of aldehydes. High enantioselectivities were obtained in reactions of both aromatic and aliphatic aldehydes (up to 84% and 86% ee, r

Enantioseparation of α-Hydroxyallylphosphonates and Phosphonoallylic Carbonate Derivatives on Chiral Stationary Phases Using Sequential UV, Polarimetric, and Refractive Index Detection

Chromatographic separation of the enantiomers of parent compounds dimethyl α-hydroxyallyl phosphonate 1a and 1-(dimethoxyphosphoryl) allyl methyl carbonate 1b was demonstrated by high-performance liquid chromatography (HPLC) using Chiralpak AS-H and ad-H chiral stationary phases (CSP), respectively, using a combination of UV, polarimetric, and refractive index detectors. A comparison was made of the separation efficiency and elution order of enantiomeric α-hydroxyallyl phosphonates and their carbonate derivatives on commercially available polysaccharide AS, ad, OD, IC-3, and Whelk-O 1 CSPs. In general, the α-hydroxyallyl phosphonates were resolved on the AS-H CSP, whereas the carbonate derivatives 1b and 2b were preferentially resolved on the ad-H CSP. The impact of aryl substitution on the resolution of analytes 1d, 1e, 1f and 2, 3, 4, 5, 6, 7, 8 was evaluated. Thermodynamic parameters determined for enantioselective adsorption hydroxyphosphonates 1a and 4 on the AS-H CSP and carbonate 1b on the ad-H CSP demonstrated enthalpic control for separation of the enantiomers. Chirality 28:656–662, 2016.

Highly enantioselective hydrophosphonylation of aldehydes: Base-enhanced aluminum-salalen catalysis

(Chemical Equation Presented) The dimethyl phosphonate hydrophosphonylation of conjugated- and non-conjugated aldehydes into their correspond ing α-hydroxy phosphonates was achieved using chiral aluminum-salalen complex 1 (see scheme).

Synthesis of cyclopentenones via intramolecular HWE and the palladium-catalyzed reactions of allylic hydroxy phosphonate derivatives

(Chemical Equation Presented) Palladium-catalyzed decarboxylative rearrangement of nonracemic phosphono allylic acetoacetates, or the intermolecular allylic substitution of nonracemic phosphono allylic carbonates with tert-butyl acetoacetate followed by h

Synthesis of an optically active al(salalen) complex and its application to catalytic hydrophosphonylation of aldehydes and aldimines

Optically active aluminum(salalen) complex 2 was newly synthesized in a modular synthetic manner, and it was found to serve as an efficient catalyst for hydrophosphonylation of aldehydes and aldimines, giving the corresponding α-hydroxy and α-amino phosph

Allylic hydroxy phosphonates: Versatile chiral building blocks

Allylic hydroxy phosphonates are converted into β and γ substituted amino phosphonates using a series of palladium-catalyzed reactions. The judicious selection of nitrogen nucleophile and palladium catalyst allow for excellent regio- and stereochemical co

Stereospecific Pd(O)-Catalyzed Malonate Additions to Allylic Hydroxy Phosphonate Derivatives: A Formal Synthesis of (-)-Enterolactone

A combination of cross-metathesis and malonate addition was applied to a formal synthesis of the mammalian lignan enterolactone 5. The cross-metathesis of alkene 6 and phosphonate 3a gave the substituted allylic phosphonate 3d. The palladium-catalyzed add

Process for preparing asymmetric compound by using metal complex

A process for producing an asymmetric compound using a metal complex containing no rare earth metal element is disclosed. The process affords an optically active compound having high optical purity. Optically active binaphthol having the chemical formula STR1 and lithium aluminum hydride are reacted, or the optically active binaphthol, a dialkyl aluminum hydride, and a base containing an alkali metal (or a base containing alkaline earth metal) are reacted to prepare a metal complex comprising optically active binaphthol, aluminum, and alkali metal (or alkaline earth metal). This metal complex can be used as a catalyst to perform an asymmetric Michael reaction, an asymmetric phosphonylation reaction, or the like, to obtain, in a high yield, an asymmetric compound having high optical purity.