Cinnamyl acetoacetate

Base Information

• Chemical Name: Cinnamyl acetoacetate
• CAS No.: 57582-46-4
• Molecular Formula: C13H14O3
• Molecular Weight: 218.252
• Hs Code.: 2918300090
• European Community (EC) Number: 260-826-4
• Nikkaji Number: J1.007.112G,J296.740E
• Mol file: 57582-46-4.mol

Synonyms:Cinnamyl 3-oxobutanoate;Cinnamyl acetoacetate;57582-46-4;EINECS 260-826-4;[(E)-3-phenylprop-2-enyl] 3-oxobutanoate;(E)-Cinnamyl3-oxobutanoate;3-Oxobutyric acid cinnamyl ester;3-phenyl-2-propenyl-3-oxobutanoate;AKOS015901653;Acetoacetic acid 3-phenyl-2-propenyl ester;Butanoic acid, 3-oxo-, 3-phenyl-2-propenyl ester;(2E)-3-PHENYLPROP-2-EN-1-YL 3-OXOBUTANOATE

Chemical Property of Cinnamyl acetoacetate

Chemical Property:

• Vapor Pressure: 2.6E-05mmHg at 25°C
• Refractive Index: 1.546
• Boiling Point: 358.1°C at 760 mmHg
• PKA: 10.44±0.46(Predicted)
• Flash Point: 158.6°C
• PSA: 43.37000
• Density: 1.107g/cm³
• LogP: 2.22210
• XLogP3: 2.1
• 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:

98%,99%, ^*data from raw suppliers

Cinnamyl3-oxobutanoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC(=O)OCC=CC1=CC=CC=C1
• Isomeric SMILES: CC(=O)CC(=O)OC/C=C/C1=CC=CC=C1

Technology Process of Cinnamyl acetoacetate

There total 4 articles about Cinnamyl acetoacetate 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: 98.0%

3-Phenylpropenol (104-54-1) + ethyl acetoacetate (141-97-9) → cinnamyl 3-oxobutanoate (57582-46-4)

Guidance literature:

With hydrotalcite-like materials supported Ag-Cu catalysts; In N,N-dimethyl-formamide; at 110 ℃; for 6h; Reagent/catalyst; Temperature; Time; Catalytic behavior; Green chemistry;

DOI:10.1039/c6ra00467a

Reference yield: 97.0%

3-Phenylpropenol (104-54-1) + acetoacetic acid methyl ester (105-45-3) → cinnamyl 3-oxobutanoate (57582-46-4)

Guidance literature:

With zinc(II) sulfate; In toluene; at 80 ℃; for 4.25h;

DOI:10.1080/00304940309355835

Reference yield: 5.0%

tert-butyl acetoacetate (1694-31-1) + 3-Phenylpropenol (104-54-1) → cinnamyl 3-oxobutanoate (57582-46-4)

Guidance literature:

With rhizopus niveus lipase; Pseudomonas sp. lipoprotein lipase; Candida antarctica lipase B immobilized on acrylic resin; Carica papaya protease; In toluene; at 40 ℃; for 48h; Enzymatic reaction;

DOI:10.1002/ejoc.201500676

upstream raw materials:

3-Phenylpropenol

ethyl acetoacetate

acetoacetic acid methyl ester

4-methyleneoxetan-2-one

Downstream raw materials:

6-phenyl-hex-5-en-2-one

3-amino-2-butenoic acid cinnamyl ester

(1α,5α)-6β-phenyl-3-oxabicyclo[3.1.0]hexan-2-one

cinnamyl 2-diazoacetate

Refernces

• 1、 Yue, Hongmei,Yu, Hao,Liu, Sheng,Xu, Chunli. "Ag-Cu nanoparticles as efficient catalysts for transesterification of β-keto esters under acid/base-free conditions". . p. 19041 - 19051. Retrieved 2016/03/01.
• 2、 Gohain, Mukut,Kumar, Vinod,Van Tonder, Johannes H.,Swart, Hendrik C.,Ntwaeaborwa, Odireleng M.,Bezuidenhoudt, Barend C. B.. "Nano CuFe2O4: An efficient, magnetically separable catalyst for transesterification of β-ketoesters". . p. 18972 - 18976. Retrieved 2015/03/04.