(5E,7Z,13E)-5,7,13-Pentadecatriene-9,11-diyn-4-ol

Base Information

• Chemical Name: (5E,7Z,13E)-5,7,13-Pentadecatriene-9,11-diyn-4-ol
• CAS No.: 97915-40-7
• Molecular Formula: C₁₅H₁₈O
• Molecular Weight: 214.307
• Mol file: 97915-40-7.mol

Synonyms:(5E,7Z,13E)-Pentadeca-5,7,13-triene-9,11-diyn-4-ol;(5E,7Z,13E)-5,7,13-Pentadecatriene-9,11-diyn-4-ol;

Chemical Property of (5E,7Z,13E)-5,7,13-Pentadecatriene-9,11-diyn-4-ol

Chemical Property:

• PSA: 20.23000
• LogP: 2.84270

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (5E,7Z,13E)-5,7,13-Pentadecatriene-9,11-diyn-4-ol

There total 18 articles about (5E,7Z,13E)-5,7,13-Pentadecatriene-9,11-diyn-4-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: 48.0%

(E)-1-bromo-3-penten-1-yne (114825-68-2) + tert-butyl(((5E,7Z)-deca-5,7-dien-9-yn-4-yl)oxy)dimethylsilane → (5E,7Z,13E)-5,7,13-Pentadecatriene-9,11-diyn-4-ol (97915-40-7)

Guidance literature:

(E)-1-bromo-3-penten-1-yne; tert-butyl(((5E,7Z)-deca-5,7-dien-9-yn-4-yl)oxy)dimethylsilane; With copper(l) iodide; tetrabutylammomium bromide; at 70 ℃; for 0.0833333h; Inert atmosphere; Darkness;

With palladium diacetate; at 70 ℃; for 12h; Inert atmosphere; Darkness;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.6b02987

Reference yield:

(E)-1-bromo-3-penten-1-yne (114825-68-2) + tert-butyl(((5E,7Z)-deca-5,7-dien-9-yn-4-yl)oxy)dimethylsilane → C15H18O + (5E,7Z,13E)-5,7,13-Pentadecatriene-9,11-diyn-4-ol (97915-40-7)

Guidance literature:

(E)-1-bromo-3-penten-1-yne; tert-butyl(((5E,7Z)-deca-5,7-dien-9-yn-4-yl)oxy)dimethylsilane; With copper(l) iodide; tetrabutylammomium bromide; at 70 ℃; for 0.0833333h; Inert atmosphere; Darkness;

With palladium diacetate; at 70 ℃; for 12h; Inert atmosphere; Darkness;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h; Overall yield = 60 %; Overall yield = 60 mg; Inert atmosphere;

DOI:10.1021/acs.joc.6b02987

Reference yield:

(E)-trimethyl(pent-3-en-1-yn-1-yl)silane (62170-41-6) → (5E,7Z,13E)-5,7,13-Pentadecatriene-9,11-diyn-4-ol (97915-40-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-Bromosuccinimide; silver nitrate / acetone / 3.5 h / 20 °C / Inert atmosphere; Darkness

2.1: tetrabutylammomium bromide; copper(l) iodide / 0.08 h / 70 °C / Inert atmosphere; Darkness

2.2: 12 h / 70 °C / Inert atmosphere; Darkness

2.3: 2 h / 20 °C / Inert atmosphere

With N-Bromosuccinimide; copper(l) iodide; tetrabutylammomium bromide; silver nitrate; In acetone; 2.1: |Cadiot-Chodkiewicz Coupling / 2.2: |Cadiot-Chodkiewicz Coupling;

DOI:10.1021/acs.joc.6b02987

upstream raw materials:

(E)-trimethyl(pent-3-en-1-yn-1-yl)silane

ethyl 2-hydroxy-n-valerate

(E)-1-bromo-3-penten-1-yne