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(2-Hydroxy-2-phenylethyl)diphenylphosphine oxide is a β-hydroxyphosphine oxide compound that can be synthesized through catalyst-free or copper-catalyzed hydroxyphosphorylation of alkenes using H-phosphine oxides and dioxygen. This reaction proceeds under mild conditions, often involving a radical process, and yields β-hydroxyphosphine oxides with good functional group tolerance. The hydroxyl group in the product originates from dioxygen, highlighting its role in the difunctionalization of alkenes. (2-hydroxy-2-phenylethyl)diphenylphosphine oxide is part of a broader class of (2-hydroxyalkyl)phosphoryl systems, which exhibit conformational and hydrogen-bonding preferences in the solid state.

100065-14-3

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100065-14-3 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 100065-14-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,0,0,6 and 5 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 100065-14:
(8*1)+(7*0)+(6*0)+(5*0)+(4*6)+(3*5)+(2*1)+(1*4)=53
53 % 10 = 3
So 100065-14-3 is a valid CAS Registry Number.

100065-14-3Relevant academic research and scientific papers

Conformational Analysis of 2-Substituted Alkylphosphoryl Compounds. 4. Substituent Effect on the Nature of the Hydrogen Bonding in (2-Hydroxyalkyl)phosphoryl Systems

Genov, Daniel G.,Kresinski, Roman A.,Tebby, John C.

, p. 2574 - 2585 (1998)

The extent to which solid state conformational and hydrogen bonding preferences of five (2-hydroxyalkyl)phosphoryl compounds 2a-e [R12P(O)CH2CH(OH)R2; 2a, R1 = MeO, R2 = Ph; 2b, R1/su

Catalyst-free direct difunctionalization of alkenes with H-phosphine oxides and dioxygen: A facile and green approach to β-hydroxyphosphine oxides

Li, Meng-Shun,Zhang, Qiang,Hu, Dong-Yan,Zhong, Wen-Wu,Cheng, Ming,Ji, Jian-Xin,Wei, Wei

, p. 2642 - 2646 (2016)

A simple and catalyst-free method has been developed for the construction of β-hydroxyphosphine oxides through direct difunctionalization of alkenes with H-phosphine oxides and dioxygen under mild conditions. Preliminary mechanistic studies indicated that the hydroxyl oxygen atom of β-hydroxyphosphine oxide originated from the dioxygen and the present reaction might involve a radical process.

Copper-catalyzed direct hydroxyphosphorylation of electron-deficient alkenes with H-phosphine oxides and dioxygen

Yi, Dong,Fu, Qiang,Chen, Su-Yuan,Gao, Ming,Yang, Lu,Zhang, Zhi-Jie,Liang, Wu,Zhang, Qiang,Ji, Jian-Xin,Wei, Wei

, p. 2058 - 2061 (2017)

A copper-catalyzed direct hydroxyphosphorylation of electron-deficient alkenes with H-phosphine oxides and dioxygen is reported. The present reaction, proceeds under mild reaction conditions with good functional group tolerance, affording the facile and efficient synthesis of various β-hydroxyphosphine oxides in a scaled-up manner with moderate to good yields.

Fast and Chemoselective Addition of Highly Polarized Lithium Phosphides Generated in Deep Eutectic Solvents to Aldehydes and Epoxides

Cicco, Luciana,Fombona-Pascual, Alba,Sánchez-Condado, Alba,Carriedo, Gabino A.,Perna, Filippo M.,Capriati, Vito,Presa Soto, Alejandro,García-álvarez, Joaquín

, p. 4967 - 4973 (2020/08/21)

Highly polarized lithium phosphides (LiPR2) were synthesized, for the first time, in deep eutectic solvents as sustainable reaction media, at room temperature and in the absence of protecting atmosphere, through direct deprotonation of both ali

Cobalt(II)-Catalyzed Bisfunctionalization of Alkenes with Diarylphosphine Oxide and Peroxide

Shen, Jian,Xiao, Bo,Hou, Yang,Wang, Xue,Li, Gui-Zhi,Chen, Jin-Chun,Wang, Wei-Li,Cheng, Jian-Bo,Yang, Bin,Yang, Shang-Dong

supporting information, p. 5198 - 5209 (2019/11/13)

The low-cost cobalt(II) catalyst has been used for the first time to achieve P(O)-radical-mediated bisfunctionalization of alkenes with diarylphosphine oxide and peroxides. This simple process is performed under mild conditions to afford a wide variety of phosphonation-peroxidation products in a one-pot manner. Computational studies are carried out to provide a theoretical support for the P(O)-radical-involved bisfunctionalization of alkenes. (Figure presented.).

INTRODUCTION REACTION OF OH GROUP AND C=O GROUP

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Paragraph 0129, (2017/08/02)

PROBLEM TO BE SOLVED: To provide an introduction reaction of a phosphoryl group and an OH group or a C=O group to alkene. SOLUTION: There is provided a manufacturing method of a product to which a phosphoryl group and an OH group or a C=O group are introduced, including a novel compound applicable to various substrates and thought to have high utility by reacting alkene and a phosphorus compound in presence of oxygen. The manufacturing method makes available to (1) reduce a residual halogen component and a residual metal component in the product, (2) easily obtain an OH group introduced compound and a C=O group introduced compound by using an oxidant and a reductant, i.e. produce 100% target and (3) reduce manufacturing cost, compared to conventional manufacturing methods. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Regio- and stereospecific cleavage of stannyloxiranes with lithium diphenylphosphide

Gonzalez-Nogal, Ana M.,Cuadrado, Purification,Sarmentero, M. Angeles

experimental part, p. 850 - 859 (2009/07/17)

Unsubstituted or C-substituted stannyloxiranes reacted stereospecifically with lithium diphenylphosphide to give either β-hydroxyphosphane oxides resulting from α-opening or β-phosphanyl ketones by β-opening. Furthermore, the reactivities of distannyloxir

Functionalized Phosphine Imides. Diastereoselective Synthesis of β-Hydroxyphosphorylated Derivatives

Barluenga, Jose,Lopez, Fernando,Palacios, Francisco

, p. 562 - 564 (2007/10/02)

The diastereoselective synthesis, of 2-hydroxyalkyldiphenylphosphine phenylimides 2 and oxides 3 by reaction of α-metallated phosphine imides with aldehydes is described.When dimethylformamide or dimethyl disulfide were used as electrophiles, functionaliz

A Simple Preparation of Vinyl- or Allyldiphenylphosphine Oxides

Santelli-Rouvier, Christiane

, p. 64 - 66 (2007/10/02)

A general route to 2- or 2,2-substituted vinyldiphenylphosphine oxides or allyldiphenylphosphine oxides from ketones (or benzaldehyde) and the anion of methyldiphenylphosphine oxide is reported.The intially formed 2-hydroxyalkyldiphenylphosphine oxide is

New Reagents, XXXIX - Optimization of the Diastereo- and Aldehyde Selectivity of Horner-Type Reagents by Modification of the Structure

Kauffmann, Thomas,Schwartze, Paul

, p. 2150 - 2158 (2007/10/02)

Introduction of an ortho-substituent in the phenyl residues of (α-lithiobutyl)diphenylphosphane oxide (7) increases the diastereoselectivity in the reaction with benzaldehyde. (α-Lithiobutyl)bis(2-methoxyphenyl)phosphane oxide (9) gave the erythro-product

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