ethyl (6E,10E)-7,11,15-trimethyl-3-oxohexadeca-6,10,14-trienoate

Base Information

• Chemical Name: ethyl (6E,10E)-7,11,15-trimethyl-3-oxohexadeca-6,10,14-trienoate
• CAS No.: 141538-75-2
• Molecular Formula: C21H34O3
• Molecular Weight: 334.499
• DSSTox Substance ID: DTXSID00450248
• Nikkaji Number: J1.556.849F
• Mol file: 141538-75-2.mol

Synonyms:141538-75-2;ethyl (6E,10E)-7,11,15-trimethyl-3-oxohexadeca-6,10,14-trienoate;ZINC22067379;DTXSID00450248;JDITVCKWSUFDMU-IJNKXORISA-N;(6E,10E)-7,11,15-Trimethyl-3-oxohexadeca-6,10,14-trienoic Acid, Ethyl Ester,;(6E,10E)-3-Oxo-7,11,15-trimethyl-6,10,14-hexadecatrienoic acid ethyl ester

Chemical Property of ethyl (6E,10E)-7,11,15-trimethyl-3-oxohexadeca-6,10,14-trienoate

Chemical Property:

• PSA: 43.37000
• LogP: 5.70810
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Hexane
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 334.25079494
• Heavy Atom Count: 24
• Complexity: 477

Purity/Quality:

97% ^*data from raw suppliers

(6E,10E)-7,11,15-Trimethyl-3-oxohexadeca-6,10,14-trienoicAcid,EthylEster,(MixtureofIsomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)CCC=C(C)CCC=C(C)CCC=C(C)C
• Isomeric SMILES: CCOC(=O)CC(=O)CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C
• Uses: A intermediate in the lipidation of proteins, which plays a great importance for a variety of biological processes such as cell signalling An intermediate in the lipidation of proteins, which plays a great importance for a variety of biological processes such as cell signalling.

Technology Process of ethyl (6E,10E)-7,11,15-trimethyl-3-oxohexadeca-6,10,14-trienoate

There total 6 articles about ethyl (6E,10E)-7,11,15-trimethyl-3-oxohexadeca-6,10,14-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: 89.0%

farnesyl bromide (24163-93-7,24163-94-8,56881-57-3,6874-67-5,28290-41-7) + sodium ethyl acetylacetate enolate (1007476-32-5) → (6E,10E)-ethyl 7,11,15-trimethyl-3-oxohexadeca-6,10,14-trienoate (141538-75-2)

Guidance literature:

sodium ethyl acetylacetate enolate; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.75h; Inert atmosphere;

farnesyl bromide; In tetrahydrofuran; hexane; at 0 ℃; Inert atmosphere;

With dipotassium hydrogenphosphate; In tetrahydrofuran; hexane;

DOI:10.1016/j.bmc.2009.12.017

Reference yield: 87.0%

farnesyl bromide (24163-93-7,24163-94-8,56881-57-3,6874-67-5,28290-41-7) + ethyl acetoacetate (141-97-9) → (6E,10E)-ethyl 7,11,15-trimethyl-3-oxohexadeca-6,10,14-trienoate (141538-75-2)

Guidance literature:

ethyl acetoacetate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.25h; Inert atmosphere;

With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.25h; Inert atmosphere;

farnesyl bromide; In tetrahydrofuran; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.114

Reference yield: 54.0%

farnesyl bromide (24163-93-7,24163-94-8,56881-57-3,6874-67-5,28290-41-7) + enolate sodique de l'acetylacetate d'ethyle (20412-62-8,66279-49-0) → (6E,10E)-ethyl 7,11,15-trimethyl-3-oxohexadeca-6,10,14-trienoate (141538-75-2)

Guidance literature:

enolate sodique de l'acetylacetate d'ethyle; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.333333h;

farnesyl bromide; In tetrahydrofuran; cyclohexane; for 0.5h;

DOI:10.1021/jm9902786

upstream raw materials:

(2E,6E)-farnesyl chloride

farnesyl bromide

enolate sodique de l'acetylacetate d'ethyle

ethyl acetoacetate

Downstream raw materials:

6,10,14-trimethyl-5,9,13-pentadecatriene-2-on

3-phenyl-7,11,15-trimethylhexadeca-2Z,6E,10E,14-tetraen-1-ol

ethyl 3-phenyl-7,11,15-trimethylhexadeca-2Z,6E,10E,14-tetraenoate

{(4E,8E)-1-[2-Chloro-eth-(Z)-ylidene]-5,9,13-trimethyl-tetradeca-4,8,12-trienyl}-benzene