Allyl 1-allyl-2-oxocyclohexanecarboxylate

Base Information

• Chemical Name: Allyl 1-allyl-2-oxocyclohexanecarboxylate
• CAS No.: 65726-93-4
• Molecular Formula: C13H18O3
• Molecular Weight: 222.284
• DSSTox Substance ID: DTXSID50504563
• Mol file: 65726-93-4.mol

Synonyms:allyl 1-allyl-2-oxocyclohexanecarboxylate;65726-93-4;DTXSID50504563;prop-2-enyl 2-oxo-1-prop-2-enylcyclohexane-1-carboxylate;AKOS015906871;Prop-2-en-1-yl 2-oxo-1-(prop-2-en-1-yl)cyclohexane-1-carboxylate

Chemical Property of Allyl 1-allyl-2-oxocyclohexanecarboxylate

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 222.125594432
• Heavy Atom Count: 16
• Complexity: 306

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CCC1(CCCCC1=O)C(=O)OCC=C

Technology Process of Allyl 1-allyl-2-oxocyclohexanecarboxylate

There total 4 articles about Allyl 1-allyl-2-oxocyclohexanecarboxylate 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: 79.0%

diallylcarbonate (15022-08-9) + allyl 2-oxocyclohexane-1-carboxylate (5453-93-0) → 2-allylcyclohexan-1-one (94-66-6) + 2,2-diallylcyclohexanone (5277-36-1) + allyl 2-allyl-1-oxocyclohexane-2-carboxylate (65726-93-4)

Guidance literature:

tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; In tetrahydrofuran; for 0.333333h; Product distribution; Mechanism; Ambient temperature; also cat. Pd(O)-P(OEt)3; reaction time and temperature; allyl β-keto-carboxylates with allylic carbonates; new method for the diallylation of ketones;

DOI:10.1016/S0040-4039(00)94297-7

Reference yield: 71.0%

diallylcarbonate (15022-08-9) + allyl 2-oxocyclohexane-1-carboxylate (5453-93-0) → allyl 2-allyl-1-oxocyclohexane-2-carboxylate (65726-93-4)

Guidance literature:

palladium; triethyl phosphite; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)94297-7

Reference yield:

allyl bromide (106-95-6) + 2-hydroxycyclohex-1-enecarboxylic acid (18709-01-8) → allyl 2-allyl-1-oxocyclohexane-2-carboxylate (65726-93-4)

Guidance literature:

With copper (I) tert-butoxide; Yield given. Multistep reaction; 1.) THF, -10 deg C, 7h, 2.) DMF, 0 deg C to r.t.;

DOI:10.1021/jo00337a032

upstream raw materials:

diallylcarbonate

allyl 2-oxocyclohexane-1-carboxylate

cyclohexanone

cyanoacetic acid

Downstream raw materials:

2-allylcyclohexan-1-one

2,2-diallylcyclohexanone