Ethyl cinnamoylacetate

Base Information

• Chemical Name: Ethyl cinnamoylacetate
• CAS No.: 1503-99-7
• Molecular Formula: C13H14O3
• Molecular Weight: 218.252
• DSSTox Substance ID: DTXSID701249226
• Mol file: 1503-99-7.mol

Synonyms:Ethyl cinnamoylacetate;KNUYHVRRBLEIHT-UHFFFAOYSA-N;DTXSID701249226;ethyl 3-oxo-5-phenyl-4-pentenoate;AB87848

Chemical Property of Ethyl cinnamoylacetate

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 218.094294304
• Heavy Atom Count: 16
• Complexity: 262

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)C=CC1=CC=CC=C1

Technology Process of Ethyl cinnamoylacetate

There total 38 articles about Ethyl cinnamoylacetate 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: 84.0%

ethyl 4-diethoxyphosphoryl-3-oxobutanoate (65043-08-5) + benzaldehyde (100-52-7) → ethyl 3-oxo-5-phenyl-4-pentenoate (1503-99-7,58369-48-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 - 60 ℃;

DOI:10.1016/0040-4039(80)80026-8

Reference yield: 77.0%

(E)-ethyl 2-diazo-3-hydroxy-5-phenylpent-4-enoate (85515-85-1) → ethyl 3-oxo-5-phenyl-4-pentenoate (1503-99-7,58369-48-5)

Guidance literature:

dirhodium tetraacetate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo050173c

Reference yield: 76.0%

(E)-ethyl 5-phenylpent-4-en-2-ynoate → ethyl 3-oxo-5-phenyl-4-pentenoate (1503-99-7,58369-48-5)

Guidance literature:

With silver hexafluoroantimonate; C₂₇H₃₆AuClN₂⁽¹⁺⁾; acetone; at 60 ℃; for 6h; Temperature; regioselective reaction;

DOI:10.1002/ejoc.201601025

upstream raw materials:

ethanol

(E)-1,1-Dichloro-5-phenyl-penta-1,4-dien-3-one

3-Aethoxy-5-phenyl-2,4-pentadiensaeure-aethylester

ethyl 3-oxo-4-(triphenylphosphoranylidene)butanoate

Downstream raw materials:

5-ethoxycarbonyl-6-styryl-2,3-dihydro-4-pyrone

1-(pyridin-2-yl)-3-styryl-1H-pyrazol-5-ol

ethyl 4-phenyl-2-oxobut-3-enoate

Refernces

• 1、 Sato, Toshio,Itoh, Toshiyuki,Fujisawa, Tamotsu. "FACILE SYNTHESIS OF β-KETOESTERS BY A COUPLING REACTION OF THE REFORMATSKY REAGENT WITH ACYL CHLORIDES CATALYZED BY A PALLADIUM COMPLEX". . p. 1559 - 1560. Retrieved 1982.
• 2、 Gandhi, Hirenkumar,O'Sullivan, Timothy P.. "Preparation of γ,δ-unsaturated-β-ketoesters: Lewis acid-catalysed C[sbnd]H insertion of ethyl diazoacetate into α,β-unsaturated aldehydes". supporting information. p. 3533 - 3535. Retrieved 2017/10/06.
• 3、 Dai, Zhipeng,Guillemette, Kate,Green, Thomas K.. "Stereoselective synthesis of aryl γ,δ-unsaturated β-hydroxyesters by ketoreductases". . p. 264 - 269. Retrieved 2013/10/21.