(2E,4Z)-2,4-Decadien-1-ol

Base Information

• Chemical Name: (2E,4Z)-2,4-Decadien-1-ol
• CAS No.: 16195-71-4
• Molecular Formula: C10H18O
• Molecular Weight: 154.252
• Hs Code.: 2905290000
• Mol file: 16195-71-4.mol

Synonyms:2(trans),4(cis)-Decadien-1-ol;(2E,4Z)-decadienol;(E,Z)-2,4-Decadien-1-ol;trans,cis-2,4-Decadienol;(2E,4Z)-decadien-1-ol;deca-2t,4c-dien-1-ol;

Chemical Property of (2E,4Z)-2,4-Decadien-1-ol

Chemical Property:

• Boiling Point: 86 °C(Press: 0.6 Torr)
• PKA: 14.20±0.10(Predicted)
• PSA: 20.23000
• Density: 0.8666 g/cm3(Temp: 4 °C)
• LogP: 2.67140

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2E,4Z)-2,4-Decadien-1-ol

There total 3 articles about (2E,4Z)-2,4-Decadien-1-ol 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: 80.0%

((E)-4-Hydroxy-but-2-enyl)-triphenyl-phosphonium; bromide (111724-06-2) + hexanal (66-25-1) → (2E,4E)-Deca-2,4-dien-1-ol (14507-02-9,16195-71-4,18409-21-7,77657-76-2,77657-81-9)

Guidance literature:

With n-butyllithium; Product distribution; 1) THF, 5 min at -78 deg C then 1 h at r.t., 2) 1 h, -78 deg C to r.t.; further base; investigation of the stereoselectivity of the condensation;

DOI:10.1016/S0040-4039(00)95650-8

Reference yield: 41.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (2E,4Z)-2,4-decadienal (25152-83-4,65909-91-3) + 1,7-Heptandiylbis(magnesiumbromid) (59321-71-0) → (2E,4Z)-2,4-decadien-1-ol (16195-71-4) + 1,7-dibromoheptane (4549-31-9) + 9-hydroxy-(10E,12Z)-octadecadien-1-oic acid methyl ester (6084-82-8,6114-34-7,6157-02-4,10075-07-7,23324-71-2,65700-62-1,69257-16-5,96393-36-1,98524-18-6,114297-06-2) + (6Z,8E,19E,21Z)-6,8,19,21-heptacosatetraene-10,18-diol

Guidance literature:

With carbon dioxide; Yield given. Multistep reaction; 1.) THF, HMPA, 1.5 h, r.t.; 2.) 3 h; 3.) ether;

DOI:10.1246/bcsj.59.2050

Reference yield:

1,-4-Decadiene (77657-80-8) → (2Z,4Z)-2,4-decadien-1-ol (77657-76-2) + (2E,4Z)-2,4-decadien-1-ol (16195-71-4) + (2Z,4E)-deca-2,4-diene-1-ol (77657-81-9) + (2E,4E)-2,4-decadien-1-ol (18409-21-7)

Guidance literature:

With fluorodimethoxyborane; dihydrogen peroxide; sec.-butyllithium; In tetrahydrofuran; Product distribution; effect of temperature and potassium t-butoxide;

DOI:10.1002/hlca.19800630832

upstream raw materials:

1,-4-Decadiene

diazomethane

(2E,4Z)-2,4-decadienal

1,7-Heptandiylbis(magnesiumbromid)

Downstream raw materials:

(3E,5Z)-1,3,5-undecatriene

isovaleric acid (2E,4Z)-2,4-decadienyl ester

(2E,4Z)-2,4-decadienal

(2E,4RS,5RS)-(±)-4,5-epoxy-(E)-2-decenal

Refernces

• 1、 Hosoda,Taguchi,Kobayashi. "Highly cis-selective Wittig reaction of oxido-allylic phosphorane with aldehyde. An efficient synthesis of 11-cis-retinoids". . p. 65 - 68. Retrieved 2007/10/02.