Ethyl 5,9,13-trimethyltetradeca-4,8,12-trienoate

Base Information

• Chemical Name: Ethyl 5,9,13-trimethyltetradeca-4,8,12-trienoate
• CAS No.: 59822-16-1
• Molecular Formula: C₁₉H₃₂O₂
• Molecular Weight: 292.462
• DSSTox Substance ID: DTXSID00300779
• Mol file: 59822-16-1.mol

Synonyms:59822-16-1;ethyl 5,9,13-trimethyltetradeca-4,8,12-trienoate;ethyl farnesylacetate;DTXSID00300779

Chemical Property of Ethyl 5,9,13-trimethyltetradeca-4,8,12-trienoate

Chemical Property:

• PSA: 26.30000
• LogP: 5.74890
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 11
• Exact Mass: 292.240230259
• Heavy Atom Count: 21
• Complexity: 382

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CCC=C(C)CCC=C(C)CCC=C(C)C

Technology Process of Ethyl 5,9,13-trimethyltetradeca-4,8,12-trienoate

There total 1 articles about Ethyl 5,9,13-trimethyltetradeca-4,8,12-trienoate 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:

(4E/Z,8Z)-Farnesylmalonic diethyl ester (26732-80-9,58456-68-1,58456-69-2,58456-70-5,58456-71-6) → (4E,8Z)-5,9,13-Trimethyl-tetradeca-4,8,12-trienoic acid ethyl ester (33883-46-4,59822-15-0,59822-16-1,59822-17-2,59822-18-3)

Guidance literature:

DOI:10.1007/BF00758769

Reference yield: 96.0%

(E,E)-5,9,13-Trimethyl-4,8,12-tetradecatrienoic acid,1-ethylester (59822-16-1) → (4E,8E,12E)-5,9,13-trimethyl-4,8,12-tetradecatrienoic acid (6040-06-8)

Guidance literature:

With sodium hydroxide; In ethanol; for 6h; Heating;

DOI:10.1016/S0968-0896(00)00212-1

Reference yield:

(E,E)-5,9,13-Trimethyl-4,8,12-tetradecatrienoic acid,1-ethylester (59822-16-1) → (6E,10E)-2-(Benzhydrylidene-amino)-7,11,15-trimethyl-hexadeca-6,10,14-trienoic acid ethyl ester (870526-99-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / DIBAL-H / toluene / -78 °C

2: CBr₄; PPh₃ / 20 °C

3: NaH / tetrahydrofuran / 0 °C

With carbon tetrabromide; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; toluene;

DOI:10.1016/j.bmcl.2005.07.075

upstream raw materials:

(4E/Z,8Z)-Farnesylmalonic diethyl ester

Downstream raw materials:

(4E,8E,12E)-5,9,13-trimethyl-4,8,12-tetradecatrienoic acid

(6E,10E)-2-Amino-7,11,15-trimethyl-hexadeca-6,10,14-trienoic acid ethyl ester

(6E,10E)-2-(Benzhydrylidene-amino)-7,11,15-trimethyl-hexadeca-6,10,14-trienoic acid ethyl ester

β-springene

Refernces