9,11-Tetradecadien-1-ol, (9E,11Z)-

Base Information

• Chemical Name: 9,11-Tetradecadien-1-ol, (9E,11Z)-
• CAS No.: 63025-02-5
• Molecular Formula: C14H26 O
• Molecular Weight: 210.36
• Hs Code.: 2905290000
• European Community (EC) Number: 263-801-6
• DSSTox Substance ID: DTXSID20886520
• Wikidata: Q82865370
• Mol file: 63025-02-5.mol

Synonyms:9,11-Tetradecadien-1-ol, (9E,11Z)-;63025-02-5;(9E,11Z)-tetradeca-9,11-dien-1-ol;EINECS 263-801-6;(Z,E)-Tetradeca-9,11-dien-1-ol;DTXSID20886520;ZKCFLTTYWFSLDK-DNVGVPOPSA-N;9,11-Tetradecadien-1-ol, (E,Z)

Chemical Property of 9,11-Tetradecadien-1-ol, (9E,11Z)-

Chemical Property:

• Vapor Pressure: 3.32E-05mmHg at 25°C
• Boiling Point: 317°C at 760 mmHg
• Flash Point: 116°C
• PSA: 20.23000
• Density: 0.86g/cm³
• LogP: 4.23180
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 10
• Exact Mass: 210.198365449
• Heavy Atom Count: 15
• Complexity: 159

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CC=CCCCCCCCCO
• Isomeric SMILES: CC/C=C\C=C\CCCCCCCCO

Technology Process of 9,11-Tetradecadien-1-ol, (9E,11Z)-

There total 9 articles about 9,11-Tetradecadien-1-ol, (9E,11Z)- 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: 85.0%

1-(2-tetrahydropyranyloxy)-(9E,11Z)-9,11-tetradecadiene (106094-39-7) → (9E,11Z)-9,11-Tetrdecadien-1-ol (63025-02-5)

Guidance literature:

With 3-tert-Butyl-4-hydroxyanisole; pyridinium p-toluenesulfonate; In ethanol; at 45 ℃; for 3h;

DOI:10.1021/jo00378a029

Reference yield:

2-dec-9-ynyloxy-tetrahydro-pyran (19754-58-6) → (9E,11Z)-9,11-Tetrdecadien-1-ol (63025-02-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) MeLi / 1.) hexane, Et₂O, a) -78 deg C, 2 h, b) -20 deg C, 15 min, 2.) hexane, Et₂O, a) -78 deg C, 0.5 h, b) 25 deg C, 2 h

2: 79 percent / diisobutylaluminum hydride / diethyl ether / 3.33 h / 25 - 40 °C

3: 1.) Br₂, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH₂Cl₂, -78 deg C, 2.) THF, CH₂Cl₂, -20 deg C

4: 63 percent / EtONa, BHA, Pd(PPh₃)4 / toluene; ethanol / 0.75 h / 65 °C

5: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 3-tert-Butyl-4-hydroxyanisole; tetrabutyl ammonium fluoride; methyllithium; bromine; sodium ethanolate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In diethyl ether; ethanol; toluene;

DOI:10.1021/jo00378a029

Reference yield:

trimethyl-(10-((tetrahydro-2H-pyran-2-yl)oxy)dec-1-yn-1-yl)silane (106094-31-9) → (9E,11Z)-9,11-Tetrdecadien-1-ol (63025-02-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / diisobutylaluminum hydride / diethyl ether / 3.33 h / 25 - 40 °C

2: 1.) Br₂, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH₂Cl₂, -78 deg C, 2.) THF, CH₂Cl₂, -20 deg C

3: 63 percent / EtONa, BHA, Pd(PPh₃)4 / toluene; ethanol / 0.75 h / 65 °C

4: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 3-tert-Butyl-4-hydroxyanisole; tetrabutyl ammonium fluoride; bromine; sodium ethanolate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In diethyl ether; ethanol; toluene;

DOI:10.1021/jo00378a029

upstream raw materials:

tetradeca-9t,11c-dienoic acid methyl ester

trans-2-pentenal

(9-hydroxynonyl)(triphenyl)phosphonium bromide

1-(2-tetrahydropyranyloxy)-(9E,11Z)-9,11-tetradecadiene

Downstream raw materials:

(9E,11Z)-tetradeca-9,11-dien-1-yl acetate

Refernces

• 1、 Bjoerkling, Fredrik,Norin, Torbjoern,Unelius, C. Rikard. "A Stereospecific Synthesis of All Four Isomers of 9,11-Tetradecadienyl Acetate Using a General Method Applicable to 1,3-Dienes". . p. 292 - 294. Retrieved 2007/10/02.