Ethyl 1-acetyl-2-ethenylcyclopropane-1-carboxylate

Base Information

• Chemical Name: Ethyl 1-acetyl-2-ethenylcyclopropane-1-carboxylate
• CAS No.: 33626-79-8
• Molecular Formula: C10H14O3
• DSSTox Substance ID: DTXSID00503041
• Nikkaji Number: J2.286.609E
• Mol file: 33626-79-8.mol

Synonyms:Ethyl 1-acetyl-2-ethenylcyclopropane-1-carboxylate;33626-79-8;SCHEMBL1412751;DTXSID00503041;ethyl 1-acetyl-2-vinylcyclopropanecarboxylate

Chemical Property of Ethyl 1-acetyl-2-ethenylcyclopropane-1-carboxylate

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 182.094294304
• Heavy Atom Count: 13
• Complexity: 257

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CC1C=C)C(=O)C

Technology Process of Ethyl 1-acetyl-2-ethenylcyclopropane-1-carboxylate

There total 3 articles about Ethyl 1-acetyl-2-ethenylcyclopropane-1-carboxylate 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: 25.0%

Z-1,4-dichlorobutene (1476-11-5) + ethyl acetoacetate (141-97-9) → ethyl 1-acetylcyclopent-3-ene-1-carboxylate (33626-80-1) + 1-acetyl-2-vinylcyclopropanecarboxylic acid ethyl ester (33626-79-8) + ethyl (4Z)-2-acetyl-6-chlorohex-4-enoate

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In acetonitrile; Microwave irradiation;

DOI:10.1134/S1070363217010248

Reference yield:

Z-1,4-dichlorobutene (1476-11-5) + acetoacetic acid ethyl ester; sodium (Z)-2-enolate → ethyl 1-acetylcyclopent-3-ene-1-carboxylate (33626-80-1) + 1-acetyl-2-vinylcyclopropanecarboxylic acid ethyl ester (33626-79-8)

Guidance literature:

Multistep reaction; (i), (ii) aq. Na₂CO₃;

Reference yield:

1,4-dichloro-2-butene (764-41-0) + ethyl acetoacetate (141-97-9) → (Z)-2-Acetyl-hexa-2,5-dienoic acid ethyl ester (58920-78-8) + ethyl 1-acetylcyclopent-3-ene-1-carboxylate (33626-80-1) + 1-acetyl-2-vinylcyclopropanecarboxylic acid ethyl ester (33626-79-8)

Guidance literature:

Multistep reaction; (i) DBU, DMF, (ii) /BRN= 1361446/;

upstream raw materials:

Z-1,4-dichlorobutene

1,4-dichloro-2-butene

ethyl acetoacetate

Downstream raw materials:

cyclopropane-1,1,2-tricarboxylic acid

1-(2-methyl-5-vinyl-4,5-dihydrofuran-3-yl)ethan-1-one