(3E)-4-hydroxypent-2-enyl diphenylphosphine oxide

Base Information

Chemical Name:(3E)-4-hydroxypent-2-enyl diphenylphosphine oxide
CAS No.:145681-36-3
Molecular Formula:C₁₇H₁₉O₂P
Molecular Weight:286.31
Hs Code.:

Synonyms:(3E)-4-hydroxypent-2-enyl diphenylphosphine oxide

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Chemical Property of (3E)-4-hydroxypent-2-enyl diphenylphosphine oxide

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Technology Process of (3E)-4-hydroxypent-2-enyl diphenylphosphine oxide

There total 4 articles about (3E)-4-hydroxypent-2-enyl diphenylphosphine oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: C₁₇H₁₇OP

: 145681-36-3
(3E)-4-hydroxypent-2-enyl diphenylphosphine oxide

: (3E,4S)-4-hydroxypent-2-enyl diphenylphosphine oxide

Guidance literature:: C₁₇H₁₇OP; With methanol; (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane; bis(pinacol)diborane; copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; at 20 ℃; for 20h; Inert atmosphere; Schlenk technique;

With sodium perborate tetrahydrate; In tetrahydrofuran; water; at 20 ℃; for 2h; Overall yield = 14 %; Overall yield = 12 mg; enantioselective reaction; Inert atmosphere; Schlenk technique;
DOI:10.1021/acs.orglett.8b03532

Reference yield:

: 145652-91-1
(E)-1-Diphenylphosphinoylpent-2-en-4-ol

: 145681-36-3
(3E)-4-hydroxypent-2-enyl diphenylphosphine oxide

: 145653-14-1
(S)-1-[(2S,3R)-3-(Diphenyl-phosphinoylmethyl)-oxiranyl]-ethanol

: 145653-14-1
(R)-1-[(2R,3S)-3-(Diphenyl-phosphinoylmethyl)-oxiranyl]-ethanol

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; In dichloromethane; at -16 ℃; for 120h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1016/S0040-4039(00)60928-0

Reference yield:

: 2129-89-7
diphenyl(methyl)phosphine oxide

: 145681-36-3
(3E)-4-hydroxypent-2-enyl diphenylphosphine oxide

: (3E,4S)-4-hydroxypent-2-enyl diphenylphosphine oxide

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 - 20 °C / Inert atmosphere

1.3: 0.17 h / -78 °C / Inert atmosphere

2.1: copper(l) chloride; (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane; bis(pinacol)diborane; sodium t-butanolate; methanol / tetrahydrofuran / 20 h / 20 °C / Inert atmosphere; Schlenk technique

2.2: 2 h / 20 °C / Inert atmosphere; Schlenk technique

With methanol; (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane; n-butyllithium; bis(pinacol)diborane; copper(l) chloride; sodium t-butanolate; In tetrahydrofuran;
DOI:10.1021/acs.orglett.8b03532