18255-62-4

Upstream product

• 100-39-0 benzyl bromide 
• 13238-16-9 dibenzylphosphine oxide 
• 217199-46-7 diphenylmethyl dibenzylphosphinothioate 
• 7369-51-9 dibenzylphosphinic acid 

Downstream Products

• 21713-63-3 methyl dibenzylphosphinate 
• 27286-15-3 dibenzyl-tert-butylphosphine oxide 
• 24442-45-3 dibenzylphenylphosphane oxide 
• 38827-92-8 Bis(bromphenylmethyl)phenylphosphanoxid 
• 84184-99-6 Benzyl(bromphenylmethyl)phenylphosphanoxid 
• 38827-92-8 meso-Bis(bromphenylmethyl)phenylphosphanoxid 
• 80918-95-2 N-(2-phenylethyl)-P,P-dibenzylphosphinamide 
• 80919-10-4 C₂₇H₃₀NO₅P 

Relevant academic research and scientific papers

Golden Face of Phosphine: Cascade Reaction to Bridgehead Methanophosphocines by Intramolecular Double Hydroarylation

Reported herein is the first example of a gold-catalyzed cyclization of bis(arylmethyl)ethynylphosphine oxides. This represents an original approach to bridgehead methanophosphocines 1, eight-membered heterocycles. Gold catalyst in combination with triflic acid activates alkyne and induces a double hydroarylation. Mechanistic studies suggest that the reaction proceeds stepwise, forming first the 1H-isophosphinoline 2-oxide 5. Reduction and protection of the corresponding phosphine oxides 1 described herein also highlight the effectiveness of our approach to this new class of electron-rich ligands.

Direct, oxidative halogenation of diaryl- or dialkylphosphine oxides with (dihaloiodo)arenes

The oxidative halogenation of diaryl- or dialkylphosphine oxides with the hypervalent iodine reagents (difluoroiodo)toluene (p-TolIF2, 1) and (dichloroiodo)benzene (PhICl2, 2) is reported. Phosphoric fluorides could be recovered in 32–75% yield, or they could be trapped with EtOH to give the corresponding phosphinate in typically good yield. Phosphoric chlorides were not readily isolable, and were trapped with alcohol and amine nucleophiles, giving diaryl- or dialkylphos-phinates and phosphinamides in up to 90% yield.

Synthesis and enzymic evaluation of 4-mercapto-6-oxo-1,4- azaphosphinane-2-carboxylic acid 4-oxide as an inhibitor of mammalian dihydroorotase

The design, synthesis, and enzymic evaluation of cis- and trans-4- mercapto-6-oxo-1,4-azaphosphinane-2-carboxylic acid 4-oxide 5 against mammalian dihydroorotase is presented. The design strategy for 5 was based on the strong affinity of phosphinothioic a

Evaluation of Phosphinic Acid Derivatives as Reagents For Amine Protection in Peptide Synthesis

The results of a kinetic study of the acid-catalysed methanolysis of a series of N-(2-phenyl-ethyl)phosphinamides incorporating selected substituents on phosphorus have been evaluated in order to define the optimum reagent and conditions for amine protection of α-amino acids during peptide synthesis.

Three-membered Ring Heterocycles, 14. α-Halogenation of Tertiary Phosphane Oxides

The symmetrically substituted tertiary phosphane oxides 5 were obtained from phosphorus halides 4 and 6 using organometallic reagents.Dibenzylphenylphosphane oxide (5c) reacted with bromine at 150 deg C to give all three possible diastereomeric α,α'-dibromophosphane oxides. e.g. (R,R/S,S)-2c, (r)-2c, and (s)-2c, and one α-bromophosphane oxide 8.The phosphane oxides 5a, b, d were lithiated once or twice in the α-positions by means of butyllithium.The α,α'-dilithiophoasphane oxides -5 reacted with tetrachloromethane below -80 deg C to yield the α-chlorophosphane oxides 1c - e whose diastereomeric ratios were controlled kinetically.The thermodynamically controlled ratios were adjusted with bases.While the α-lithiated dineopentyl phosphane oxides -5a and -5d also afforded the α-chlorophosphane oxides 1c and 1d, respectively, with an excess of tetrachloromethane, the α,α-dichlorophosphane oxide 9 was formed from the α-lithiobenzylphosphane oxide 5b.This difference is attributed to the acidity of the α-protons and steric factors.The configurations and preferred conformations of the α,α'-dibromophosphane oxides 2c and the α-chlorophosphane oxides 1c - e were determined on the basis of the 1H-31P coupling of the methine protons.

Process for producing cholestane type steroids

A process for producing cholestanyl phosphate or epicholestanyl phosphate or salts thereof in which the hydroxyl group at the three-position of cholestanol or epicholestanol is converted into the phosphoric ester by reaction with a phosphorylating agent in an inert solvent and hydrolyzing or hydrogenating this ester.