(4-Methylpent-3-en-1-yl)diphenylphosphine oxide

Base Information

• Chemical Name: (4-Methylpent-3-en-1-yl)diphenylphosphine oxide
• CAS No.: 86105-38-6
• Molecular Formula: C18H21OP
• Molecular Weight: 284.338
• DSSTox Substance ID: DTXSID90453586
• Nikkaji Number: J1.324.793E
• Mol file: 86105-38-6.mol

Synonyms:(4-Methylpent-3-en-1-yl)diphenylphosphine oxide;86105-38-6;[4-methylpent-3-enyl(phenyl)phosphoryl]benzene;(4-Methyl-3-pentenyl)diphenylphosphine oxide;(4-methyl-3-penten-1-yl) diphenyl phosphine oxide;(4-Methylpent-3-en-1-yl)diphenylphosphineoxide;DTXSID90453586;AKOS016005644;CS-0203254;FT-0715126;(4-methyl-3-penten-1-yl)diphenyl phosphine oxide;[(4-methylpent-3-en-1-yl)(phenyl)phosphoroso]benzene;(4-Methylpent-3-en-1-yl)(oxo)diphenyl-lambda~5~-phosphane

Chemical Property of (4-Methylpent-3-en-1-yl)diphenylphosphine oxide

Chemical Property:

• PSA: 26.88000
• LogP: 4.35680
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 284.133002287
• Heavy Atom Count: 20
• Complexity: 334

Purity/Quality:

99%min ^*data from raw suppliers

(4-Methylpent-3-en-1-yl)diphenylphosphine oxide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCP(=O)(C1=CC=CC=C1)C2=CC=CC=C2)C

Technology Process of (4-Methylpent-3-en-1-yl)diphenylphosphine oxide

There total 3 articles about (4-Methylpent-3-en-1-yl)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:

isoprene (78-79-5,9003-31-0) → (4-Methyl-3-pentenyl) diphenylphosphine oxide (86105-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / HBr / acetic acid / 48 h / 4 °C

2: 1.) n-BuLi / 1.) Et₂O, hexane, 30 min; 2.) Et₂O, -78 deg C -> 20 deg C

With n-butyllithium; hydrogen bromide; In acetic acid;

Reference yield:

prenyl bromide (870-63-3) + diphenyl(methyl)phosphine oxide (2129-89-7) → (4-Methyl-3-pentenyl) diphenylphosphine oxide (86105-38-6) + <4-methyl-1-(3'-methyl-2'-butenyl)pent-3-enyl>diphenylphosphane oxide (115693-97-5)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) Et2O, hexane, 30 min; 2.) Et2O, -78 deg C -> 20 deg C;

Reference yield:

prenyl bromide (870-63-3) + diphenyl(methyl)phosphine oxide (2129-89-7) → (4-Methyl-3-pentenyl) diphenylphosphine oxide (86105-38-6)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction;

DOI:10.1016/S0040-4039(00)81341-6

upstream raw materials:

prenyl bromide

diphenyl(methyl)phosphine oxide

isoprene

Downstream raw materials:

(2R,3R)-3-(Diphenyl-phosphinoyl)-6-methyl-2-(4-methyl-cyclohex-3-enyl)-hept-5-en-2-ol

(2S,3R)-3-(Diphenyl-phosphinoyl)-6-methyl-2-(4-methyl-cyclohex-3-enyl)-hept-5-en-2-ol

(5-diphenylphosphinoyl)-2-methyl-3-pentanol

erythro-(1R,2S,4S)-4-(1',5'-Dimethyl-2'-diphenylphosphinoyl-1'-hydroxyhex-4'-enyl)-1,2-epoxy-1-methylcyclohexane

Refernces

• 1、 Buss, Antony D.,Greeves, Nicholas,Mason, Ralph,Warren, Stuart. "Applications of the Stereochemically-Controlled Horner-Wittig Reaction: Synthesis of Feniculin, (E)-Non-6-en-1-ol, a Pheromone of the Mediterranean Fruit Fly, (E)- and (Z)-Dec-5-en-1-ol, Tri-substituted Alkenes, and (Z)-α-Bisabolene". . p. 2569 - 2578. Retrieved 2007/10/02.
• 2、 Buss, Antony D.,Warren, Stuart. "THE WITTIG-HORNER ROUTE TO TRI-SUBSTITUTED ALKENES: SYNTHESIS OF Z-α-BISABOLENE". . p. 111 - 114. Retrieved 2007/10/02.