Cyclohex-2-en-1-yl 3-oxobutanoate

Base Information

• Chemical Name: Cyclohex-2-en-1-yl 3-oxobutanoate
• CAS No.: 61363-92-6
• Molecular Formula: C10H14O3
• Molecular Weight: 182.219
• DSSTox Substance ID: DTXSID70565151
• Nikkaji Number: J2.112.128B
• Mol file: 61363-92-6.mol

Synonyms:Cyclohex-2-en-1-yl 3-oxobutanoate;61363-92-6;DTXSID70565151;2-cyclohexen-1-yl 3-oxobutanoate;3-oxo-butyric acid 1-cyclohex-2-enyl ester

Chemical Property of Cyclohex-2-en-1-yl 3-oxobutanoate

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 182.094294304
• Heavy Atom Count: 13
• Complexity: 230

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC(=O)OC1CCCC=C1

Technology Process of Cyclohex-2-en-1-yl 3-oxobutanoate

There total 4 articles about Cyclohex-2-en-1-yl 3-oxobutanoate 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: 90.0%

acetoacetic acid methyl ester (105-45-3) + Cyclohex-2-enol (822-67-3) → cyclohex-2-enyl 3-oxobutanoate (61363-92-6)

Guidance literature:

With copper ferrite; In toluene; for 8h; Reflux;

DOI:10.1039/c4ra15014g

Reference yield: 85.0%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + Cyclohex-2-enol (822-67-3) → cyclohex-2-enyl 3-oxobutanoate (61363-92-6)

Guidance literature:

With dmap; In diethyl ether; for 0.5h; Inert atmosphere;

DOI:10.1021/ol901046z

Reference yield: 81.1%

diketene (88996-98-9) + Cyclohex-2-enol (822-67-3) → cyclohex-2-enyl 3-oxobutanoate (61363-92-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/jo00011a031

upstream raw materials:

4-methyleneoxetan-2-one

Cyclohex-2-enol

diketene

bromoacetic acid cyclohex-2-enyl ester

Downstream raw materials:

2-cyclohexenyl 3-hydroxybutanoate

2-cyclohexenyl 3-hydroxybutanoate

cyclohex-2-enyl acetoacetate

1-(2'-cyclohexenyl)-2-propanone

Refernces

• 1、 Newhouse, Timothy R.,Kaib, Philip S. J.,Gross, Andrew W.,Corey. "Versatile approaches for the synthesis of fused-ring γ-lactones utilizing cyclopropane intermediates". supporting information. p. 1591 - 1593. Retrieved 2013/06/27.
• 2、 Park, Heui Sul,Lee, In Sang,Kim, Yong Hae. "Facile synthesis of β-ketoesters mediated by Sml2: Reformatsky reaction type selfcondensation". . p. 1673 - 1674. Retrieved 2007/10/02.