(E)-4,8-Dimethyl-1,3,7-nonatriene

Base Information

• Chemical Name: (E)-4,8-Dimethyl-1,3,7-nonatriene
• CAS No.: 19945-61-0
• Molecular Formula: C11H18
• Molecular Weight: 150.264
• European Community (EC) Number: 257-509-8
• DSSTox Substance ID: DTXSID7068685,DTXSID201304588
• Nikkaji Number: J294.944J,J398.668C
• Wikidata: Q27127102
• Metabolomics Workbench ID: 4738
• Mol file: 19945-61-0.mol

Synonyms:(3E)-4,8-dimethyl-1,3,7-nonatriene;3E-DMNT;4,8-dimethyl-1,3,7-nonatriene;4,8-dimethylnona-1,3,7-triene;DMNT cpd

Chemical Property of (E)-4,8-Dimethyl-1,3,7-nonatriene

Chemical Property:

• Vapor Pressure: 0.582mmHg at 25°C
• Boiling Point: 195.6°Cat760mmHg
• Flash Point: 60.4°C
• PSA: 0.00000
• Density: 0.782g/cm³
• LogP: 3.86510
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 150.140850574
• Heavy Atom Count: 11
• Complexity: 167

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (E)-4,8-Dimethyl-1,3,7-nonatriene

There total 33 articles about (E)-4,8-Dimethyl-1,3,7-nonatriene 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%

3,7-dimethyl-2,6-octadienal (141-27-5,96680-15-8) + Methyltriphenylphosphonium bromide (1779-49-3) → (E)-4,8-dimethylnona-1,3,7-triene (19945-61-0)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 - 25 ℃;

DOI:10.1016/j.tetlet.2006.12.119

Reference yield: 91.0%

geranyl mesylate (78130-96-8) + methylenetriphenylarsorane (47025-43-4,19365-61-8) → (E)-4,8-dimethylnona-1,3,7-triene (19945-61-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(97)10152-6

Reference yield: 90.0%

3,7-dimethyl-2,6-octadienal (141-27-5,96680-15-8) + diazomethyl-trimethyl-silane (18107-18-1) → (E)-4,8-dimethylnona-1,3,7-triene (19945-61-0)

Guidance literature:

With Wilkinson's catalyst; triphenylphosphine; isopropyl alcohol; In tetrahydrofuran; at 25 ℃; for 2h;

DOI:10.1021/ja038112o

upstream raw materials:

Vinyl bromide

2-methylhept-2-en-6-yne

trimethylaluminum

diiodomethane

Downstream raw materials:

(1S,2S,3S,4R)-1,3-dimethyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-diol

(1R,2R,3R,4S)-1,3-dimethyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-diol

(1S,2S,3S,4R)-1-((benzyloxy)methyl)-3-methyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-diol

(1R,2R,3R,4S)-1-((benzyloxy)methyl)-3-methyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-diol

Refernces

• 1、 Luo, Shao-Xiong,Cannon, Jeffrey S.,Taylor, Buck L. H.,Engle, Keary M.,Houk,Grubbs, Robert H.. "Z-Selective Cross-Metathesis and Homodimerization of 3E-1,3-Dienes: Reaction Optimization, Computational Analysis, and Synthetic Applications". . p. 14039 - 14046. Retrieved 2016.
• 2、 Lee, Sungbeom,Badieyan, Somayesadat,Bevan, David R.,Herde, Marco,Gatz, Christiane,Tholl, Dorothea. "Herbivore-induced and floral homoterpene volatiles are biosynthesized by a single P450 enzyme (CYP82G1) in Arabidopsis". . p. 21205 - 21210. Retrieved 2010.
• 3、 Goetz, Daniel B.,Holstein, Sarah A.,Varney, Michelle L.,Wiemer, David F.. "Amides as bioisosteres of triazole-based geranylgeranyl diphosphate synthase inhibitors". . . Retrieved 2020/07/10.
• 4、 Liao, Lihao,Guo, Ruizhi,Zhao, Xiaodan. "Organoselenium-Catalyzed Regioselective C?H Pyridination of 1,3-Dienes and Alkenes". . p. 3201 - 3205. Retrieved 2017/03/17.