Diethyl (E)-(3,7-dimethyl-2,6-octadienyl)malonate

Base Information

• Chemical Name: Diethyl (E)-(3,7-dimethyl-2,6-octadienyl)malonate
• CAS No.: 19894-79-2
• Molecular Formula: C17H28 O4
• Molecular Weight: 296.407
• Hs Code.: 2917190090
• European Community (EC) Number: 243-408-6
• DSSTox Substance ID: DTXSID401170050
• Nikkaji Number: J280.396H
• Mol file: 19894-79-2.mol

Synonyms:Diethyl (E)-(3,7-dimethyl-2,6-octadienyl)malonate;19894-79-2;EINECS 243-408-6;diethyl 2-[(2E)-3,7-dimethylocta-2,6-dienyl]propanedioate;diethyl geranylmalonate;DTXSID401170050;[(2E)-3,7-Dimethyl-2,6-octadienyl]malonic acid diethyl ester;1,3-Diethyl 2-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]propanedioate

Chemical Property of Diethyl (E)-(3,7-dimethyl-2,6-octadienyl)malonate

Chemical Property:

• Vapor Pressure: 4.22E-05mmHg at 25°C
• Boiling Point: 351.1°Cat760mmHg
• Flash Point: 160.8°C
• PSA: 52.60000
• Density: 0.977g/cm³
• LogP: 3.81160
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 296.19875937
• Heavy Atom Count: 21
• Complexity: 372

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Diethyl (E)-(3,7-dimethyl-2,6-octadienyl)malonate

There total 37 articles about Diethyl (E)-(3,7-dimethyl-2,6-octadienyl)malonate 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: 91.0%

trans-geranyl bromide (6138-90-5) + diethyl malonate (105-53-3) → diethyl [(2E)-3,7-dimethylocta-2,6-dienyl]malonate (19894-79-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1021/ol201028f

Reference yield: 63.0%

1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) + diethyl malonate (105-53-3) → diethyl [(2E)-3,7-dimethylocta-2,6-dienyl]malonate (19894-79-2)

Guidance literature:

With lithium hydroxide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; at 20 ℃; for 2h;

DOI:10.1023/B:RUCB.0000035652.61455.b9

Reference yield: 31.0%

Geraniol (106-24-1) + diethyl malonate (105-53-3) → diethyl [(2E)-3,7-dimethylocta-2,6-dienyl]malonate (19894-79-2) + 2-(1,5-Dimethyl-1-vinyl-hex-4-enyl)-malonic acid diethyl ester (99372-02-8)

Guidance literature:

With triethyl borane; sodium hydride; triphenylphosphine; palladium diacetate; In tetrahydrofuran; hexane; at 50 ℃; for 20h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(00)00934-5

upstream raw materials:

trans-geranyl bromide

diethyl malonate

7-methyl-3-methene-1,6-octadiene

1-chloro-3,7-dimethylocta-2,6-diene

Downstream raw materials:

geranyl cyanide

diethyl (E)-2-(3,7-dimethyl-2,6-octadienyl)-2-(2-propenyl)malonate

geranylacetic acid

diethyl [(2E)-3,7-dimethylocta-2,6-dien-1-yl](cyclohexyl)malonate