(Z,Z)-Tetradeca-9,11-dienyl acetate

Base Information

• Chemical Name: (Z,Z)-Tetradeca-9,11-dienyl acetate
• CAS No.: 54664-97-0
• Molecular Formula: C16H28 O2
• Molecular Weight: 252.397
• Hs Code.: 2915390090
• European Community (EC) Number: 259-286-2
• UNII: MG8Z972A78
• DSSTox Substance ID: DTXSID601251751
• Metabolomics Workbench ID: 3969
• Mol file: 54664-97-0.mol

Synonyms:(Z,Z)-Tetradeca-9,11-dienyl acetate;54664-97-0;9,11-Tetradecadien-1-ol, 1-acetate, (9Z,11Z)-;9Z,11Z-Tetradecadienyl acetate;9,11-Tetradecadien-1-ol, acetate, (9Z,11Z)-;EINECS 259-286-2;(9Z,11Z)-9,11-Tetradecadien-1-yl acetate;9,11-Tetradecadien-1-ol, acetate, (Z,Z)-;SCHEMBL1301380;DTXSID601251751;MG8Z972A78;z,z-9,11-tetradecadienyl acetate;LMFA07010324;(9Z,11Z)-9,11-tetradecadienyl acetate;1-Acetoxy-9,11-tetradecadien-1-ol, (9Z,11Z)-

Chemical Property of (Z,Z)-Tetradeca-9,11-dienyl acetate

Chemical Property:

• Vapor Pressure: 6.47E-06mmHg at 25°C
• Boiling Point: 378°C at 760 mmHg
• Flash Point: 107.1°C
• PSA: 26.30000
• Density: 0.89g/cm³
• LogP: 4.80260
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 12
• Exact Mass: 252.208930132
• Heavy Atom Count: 18
• Complexity: 242

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CC=CCCCCCCCCOC(=O)C
• Isomeric SMILES: CC/C=C\C=C/CCCCCCCCOC(=O)C

Technology Process of (Z,Z)-Tetradeca-9,11-dienyl acetate

There total 32 articles about (Z,Z)-Tetradeca-9,11-dienyl acetate 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: 84.2%

(9Z,11Z)-9,11-Tetradecadien-1-ol (72553-59-4) + acetic anhydride (108-24-7) → (9Z,11Z)-9,11-tetradecadienol acetate (54664-97-0)

Guidance literature:

With pyridine; In water; toluene; at 20 - 40 ℃; for 5h;

Reference yield:

2-(8-bromooctyloxy)tetrahydropyran (50816-20-1) → (9Z,11Z)-9,11-tetradecadienol acetate (54664-97-0)

Guidance literature:

Multi-step reaction with 6 steps

1: LiNH₂; NH₃

2: H₂ / Lindlar catalyst / ethanol / 0 °C

3: MnO₂ / toluene

4: t-BuOK / tetrahydrofuran

5: p-TsOH / methanol

6: pyridine

With pyridine; manganese(IV) oxide; lithium amide; potassium tert-butylate; ammonia; hydrogen; toluene-4-sulfonic acid; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; toluene; 1: Substitution / 2: Hydrogenation / 3: Oxidation / 4: Wittig reaction / 5: Hydrolysis / 6: Acetylation;

DOI:10.1007/BF02027728

Reference yield:

11-(tetrahydro-2H-pyran-2-yloxy)undec-2-yn-1-ol (87242-02-2) → (9Z,11Z)-9,11-tetradecadienol acetate (54664-97-0)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Lindlar catalyst / ethanol / 0 °C

2: MnO₂ / toluene

3: t-BuOK / tetrahydrofuran

4: p-TsOH / methanol

5: pyridine

With pyridine; manganese(IV) oxide; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; toluene; 1: Hydrogenation / 2: Oxidation / 3: Wittig reaction / 4: Hydrolysis / 5: Acetylation;

DOI:10.1007/BF02027728

upstream raw materials:

pent-2-yn-1-al

(9-Acetoxynonyl)-triphenylphosphonium-bromid

methyl magnesium iodide

propylidenetriphenylphosphorane

Refernces

• 1、 Zhu, Junwei,Ryrholm, Nils,Ljungberg, Hakan,Hansson, Bill S.,Hall, David,Reed, Darwin,Loefstedt, Christer. "Olefinic acetates, Δ-9,11-14:OAc and Δ-7,9-12:OAc used as sex pheromone components in three geometrid moths, Idaea aversata, I. straminata, and I. biselata (Geometridae, Lepidoptera)". . p. 1505 - 1526. Retrieved 2007/10/03.
• 2、 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.