ethyl (2Z,4E)-3,7,11-trimethyldodeca-2,4-dienoate

Base Information

• Chemical Name: ethyl (2Z,4E)-3,7,11-trimethyldodeca-2,4-dienoate
• CAS No.: 41096-47-3
• Molecular Formula: C17H30O2
• Molecular Weight: 266.4189
• DSSTox Substance ID: DTXSID401179402
• Nikkaji Number: J955.684B
• Mol file: 41096-47-3.mol

Synonyms:ethyl (2Z,4E)-3,7,11-trimethyldodeca-2,4-dienoate;41096-47-3;DTXSID401179402;(2E,4E)-ethyl 3,7,11-trimethyldodeca-2,4-dienoate;(2Z,4E)-3,7,11-Trimethyl-2,4-dodecadienoic acid ethyl ester;2,4-Dodecadienoic acid, 3,7,11-trimethyl-, ethyl ester, (Z,E)-

Chemical Property of ethyl (2Z,4E)-3,7,11-trimethyldodeca-2,4-dienoate

Chemical Property:

• Vapor Pressure: 9.36E-05mmHg at 25°C
• Boiling Point: 339.2°Cat760mmHg
• Flash Point: 153.8°C
• Density: 0.886g/cm³
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 266.224580195
• Heavy Atom Count: 19
• Complexity: 300

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=C(C)C=CCC(C)CCCC(C)C
• Isomeric SMILES: CCOC(=O)/C=C(/C)\C=C\CC(C)CCCC(C)C

Technology Process of ethyl (2Z,4E)-3,7,11-trimethyldodeca-2,4-dienoate

There total 38 articles about ethyl (2Z,4E)-3,7,11-trimethyldodeca-2,4-dienoate 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: 92.0%

(2E,4E)-3,7,11-trimethyl-2,4-dodecadienoic acid + diethyl dicarbonate (1609-47-8) → (S)-hydroprene (36557-30-9,41096-46-2,41096-47-3,41205-09-8,53042-55-0,53042-72-1,53042-73-2,53833-71-9,57378-83-3,57378-84-4,65733-19-9,65733-18-8)

Guidance literature:

With dmap; In toluene; at 15 - 25 ℃; for 2h; Reagent/catalyst; Solvent; Temperature; Green chemistry;

Reference yield: 79.0%

C11H23BO2 (1356399-81-9) + ethyl (E)-3-(trifluoromethylsulfonyloxy)but-2-enoate (122135-84-6,137273-43-9,122135-96-0) → (S)-hydroprene (36557-30-9,41096-46-2,41096-47-3,41205-09-8,53042-55-0,53042-72-1,53042-73-2,53833-71-9,57378-83-3,57378-84-4,65733-19-9,65733-18-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; at 80 ℃; for 20h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.02.019

Reference yield: 30.0%

ethyl 4-bromo-3,7,11-trimethyl-2ξ-dodecenoate (122367-19-5) → Ethyl-3,7,11-Trimethyl-cis-2,trans-4-dodecadienoat (41096-47-3) + hydroprene (41096-46-2)

Guidance literature:

With lithium carbonate; lithium bromide; In N,N-dimethyl-formamide; for 2h; Yield given. Title compound not separated from byproducts; Heating;

upstream raw materials:

3,7-dimethyl-1-octanal

diisopropyl (2ξ)-(3-carboethoxy-2-methyl-2-propenyl)phosphonate

3E 6,10-dimethyl-3-undecen-2-one

ethoxyethynylmagnesium bromide

Refernces

• 1、 Zhang, Shunji,Dong, Huaide,Gui, Jinghan,Tian, Weisheng. "Stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene through Suzuki-Miyaura cross-coupling". . p. 1882 - 1884. Retrieved 2012/05/05.
• 2、 Gamalevich,Zhdankina,Kryshtal',Nikishin,Ogibin,Serebryakov. "Combined Biochemical and Electrochemical Approach to Chiral C10-Components for Juvenoid Synthesis, and Preparation of (2E,4E,7S)Stereoisomers of Metoprene and Hydroprene". . p. 467 - 474. Retrieved 2007/10/03.