3E,8Z-Tetradecadienyl acetate

Base Information

• Chemical Name: 3E,8Z-Tetradecadienyl acetate
• CAS No.: 163041-87-0
• Molecular Formula: C16H28O2
• Molecular Weight: 0.00000
• European Community (EC) Number: 682-690-9
• Nikkaji Number: J699.699J
• Wikidata: Q76415797
• Metabolomics Workbench ID: 3946
• Mol file: 163041-87-0.mol

Synonyms:163041-87-0;3E,8Z-Tetradecadienyl acetate;(E,Z)-3,8-Tetradecadienyl acetate;3,8-Tetradecadien-1-ol, acetate, (3E,8Z)- (9CI);[(3E,8Z)-tetradeca-3,8-dienyl] acetate;(3E,8Z)-TETRADECA-3,8-DIEN-1-YL ACETATE;(3E,8Z)-3,8-tetradecadien-1-yl acetate;3,8-Tetradecadien-1-ol, 1-acetate, (3E,8Z)-;SCHEMBL1301284;E,Z-3,8-Tetradecadienyl acetate;WWXVCCMNRBSSKV-LQZWXTFHSA-N;LMFA07010301;(3E,8Z)-3,8-tetradecadienyl acetate;(3E,8Z)-TETRADECA-3,8-DIEN-1-YLACETATE;A848815;(E,Z)-3,8-Tetradecadien-1-ol acetate CAS 163041-87-0

Chemical Property of 3E,8Z-Tetradecadienyl acetate

Chemical Property:

• PSA: 0.00000
• LogP: 0.00000
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 5.3
• 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:

99.3% ^*data from raw suppliers

3E,8Z-TetradecadienylAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC=CCCCC=CCCOC(=O)C
• Isomeric SMILES: CCCCC/C=C\CCC/C=C/CCOC(=O)C
• Uses: 3E,8Z-Tetradecadienyl Acetate is a sex pheromone of S. absoluta (Lepidoptera:Gelechiidae). It is derived from cis-4-Decen-1-ol (D225630), which is a reactant in the synthesis of epoxyisoprostanes as anti-inflammatory agents.

Technology Process of 3E,8Z-Tetradecadienyl acetate

There total 34 articles about 3E,8Z-Tetradecadienyl 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: 93.0%

acetic anhydride (108-24-7) + (E3,Z8)-3,8-tetradecadienyl alcohol (177408-62-7) → (3E,8Z)-3,8-tetradecadien-1-yl acetate (163041-87-0)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 4h; stereoselective reaction; Inert atmosphere;

DOI:10.1055/s-0034-1379977

Reference yield: 72.0%

(8Z)-Tetradecen-4-ynol → (3E,8Z)-3,8-tetradecadien-1-yl acetate (163041-87-0)

Guidance literature:

With pyridine; acetic anhydride; In diethylene glycol dimethyl ether;

Reference yield:

1-(tetrahydropyranyloxy)-4-pentyn (62992-46-5) → (3E,8Z)-3,8-tetradecadien-1-yl acetate (163041-87-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 58 percent / n-BuLi; DMPU / hexane; tetrahydrofuran / 0 °C

2: 85 percent / H₂ / P₂-Ni / ethanol / 4 h

3: 90 percent / Br₂; PPh₃ / CH₂Cl₂ / 0 °C

4: 52 percent / n-BuLi; DMPU / hexane; tetrahydrofuran / 0 °C

5: 107 mg / Dowex 50WX₈ / methanol / 20 °C

6: LiAlH₄ / bis-(2-methoxy-ethyl) ether / 3 h / 120 °C

7: 18 mg / pyridine

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium aluminium tetrahydride; n-butyllithium; dowex 50Wx₈; hydrogen; bromine; triphenylphosphine; P₂-Ni; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; diethylene glycol dimethyl ether; 1: Alkylation / 2: Catalytic hydrogenation / 3: Substitution / 4: Alkylation / 5: ether cleavage / 6: Reduction / 7: Esterification;

DOI:10.1007/BF02033586

upstream raw materials:

acetic anhydride

(E₃,Z₈)-3,8-tetradecadienyl alcohol

1-(tetrahydropyranyloxy)-4-pentyn

1-Bromopentane

Refernces

• 1、 Griepink, Frans C.,Van Beek, Teris A.,Posthumus, Maarten A.,De Groot, Aede,Visser, J. Hans,Voerman, Simon. "Identification of the sex pheromone of Scrobipalpula absolute; determination of double bond positions in triple unsaturated straight chain molecules by means of dimethyl disulphide derivatization". . p. 411 - 414. Retrieved 1996.
• 2、 -. "5-ACETOXY-(E3)-3-PENTENYL METHOXYMETHYL ETHER AND METHOD FOR PREPARING (E3)-3-ALKENYL ACETATE USING THE SAME". Paragraph 0034; 0035; 0036. . Retrieved 2013/09/26.