9Z,12Z-Tetradecadienyl acetate

Base Information

• Chemical Name: 9Z,12Z-Tetradecadienyl acetate
• CAS No.: 51354-22-4
• Deprecated CAS: 160010-60-6
• Molecular Formula: C16H28O2
• Molecular Weight: 252.397
• European Community (EC) Number: 250-753-6
• UNII: 9MXT6E7MUS
• Metabolomics Workbench ID: 3970
• Nikkaji Number: J3.422.589C
• Mol file: 51354-22-4.mol

Synonyms:cis-9-trans-12-tetradecadien-1-ol acetate;cis-9-trans-12-tetradecadien-1-ol acetate, (E,Z)-isomer

Chemical Property of 9Z,12Z-Tetradecadienyl acetate

Chemical Property:

• 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% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 9Z,12Z-Tetradecadienyl acetate

There total 9 articles about 9Z,12Z-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: 83.0%

(Z,E)-9,12-tetradecadien-1-ol (70654-44-3,51937-00-9) + acetic anhydride (108-24-7) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1) + (9E,12E)-tetradeca-9,12-dien-1-yl acetate (70654-47-6) + (Z,Z)-9,12-tetradecadienyl acetate (51354-22-4) + (9E,12Z)-9,12-tetradecadienyl acetate (31654-77-0)

Guidance literature:

In pyridine;

Reference yield: 27.0%

1,3-propanediylidenebis(triphenylphosphorane) (63591-90-2) + 9-acetoxynonal (29541-97-7) + acetaldehyde (75-07-0,9002-91-9) → trans,trans-2,5-Heptadien (39619-60-8) + (Z,Z)-9,12-tetradecadienyl acetate (51354-22-4) + Acetic acid (9E,12E)-21-acetoxy-henicosa-9,12-dienyl ester

Guidance literature:

In diethyl ether; for 14h; -78 deg C to r.t.;

DOI:10.1055/s-1990-27089

Reference yield:

1,9-Nonanediol (3937-56-2) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1) + (Z,Z)-9,12-tetradecadienyl acetate (51354-22-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 20 °C / Inert atmosphere; Schlenk technique

1.2: 2 h / 0 °C / Inert atmosphere; Schlenk technique

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere; Schlenk technique

2.2: 20 °C / Inert atmosphere; Schlenk technique

3.1: n-butyllithium / tetrahydrofuran; hexane / 0 - 20 °C / Inert atmosphere; Schlenk technique

3.2: 0.25 h / -78 °C / Inert atmosphere; Schlenk technique

3.3: -78 - 20 °C / Inert atmosphere; Schlenk technique

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Schlenk technique

5.1: triethylamine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere; Schlenk technique

6.1: zinc; zinc(II) iodide; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); diphenylphosphane / dichloromethane / 8 h / -15 °C / Inert atmosphere; Schlenk technique

With dmap; n-butyllithium; oxalyl dichloride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; diphenylphosphane; zinc(II) iodide; zinc; In tetrahydrofuran; hexane; dichloromethane; mineral oil; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation / 3.1: |Wittig Olefination / 3.2: |Wittig Olefination / 3.3: |Wittig Olefination;

DOI:10.1021/acs.orglett.5b01230

upstream raw materials:

(Z,E)-9,12-tetradecadien-1-ol

acetic anhydride

Tetradeca-cis-9,trans-12-dien-1-ol

1,3-propanediylidenebis(triphenylphosphorane)

Refernces

• 1、 Bestmann,Zeibig,Vostrowsky. "-". . p. 1039 - 1047. Retrieved 2007/10/02.
• 2、 Bestmann,Dotzer,Manero-Alvarez. "Pheromones. 48. New synthesis of (n,n+3) alkadienes". . p. 2769 - 2772. Retrieved 2007/10/02.