57582-46-4

Basic information

• Product Name: cinnamyl acetoacetate
• Synonyms: cinnamyl acetoacetate;3-Oxobutanoic acid 3-phenyl-2-propenyl ester;3-Oxobutyric acid-3-phenyl-2-propenyl ester;Acetoacetic acid 3-phenyl-2-propenyl ester;Einecs 260-826-4;cinmyl acetoacetate
• CAS NO: 57582-46-4
• Molecular Formula: C₁₃H₁₄O₃
• Molecular Weight: 218.24846
• EINECS: 260-826-4
• Mol File: 57582-46-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 358.1°C at 760 mmHg
• Flash Point: 158.6°C
• Appearance: /
• Density: 1.107g/cm³
• Vapor Pressure: 2.6E-05mmHg at 25°C
• Refractive Index: 1.546
• PKA: 10.44±0.46(Predicted)
• CAS DataBase Reference: cinnamyl acetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: cinnamyl acetoacetate(57582-46-4)
• EPA Substance Registry System: cinnamyl acetoacetate(57582-46-4)

Safety Data

• Hazardous Substances Data: 57582-46-4(Hazardous Substances Data)

Usage

Chemical Properties

Light brown liquid

InChI:InChI=1/C13H14O3/c1-11(14)10-13(15)16-9-5-8-12-6-3-2-4-7-12/h2-8H,9-10H2,1H3/b8-5+

Upstream product

• 104-54-1 3-Phenylpropenol 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 674-82-8 4-methyleneoxetan-2-one 
• 1694-31-1 tert-butyl acetoacetate 

Downstream Products

• 69371-59-1 6-phenyl-hex-5-en-2-one 
• 188626-56-4 cinnamyl 2-diazoacetate 
• 132435-61-1 (1α,5α)-6β-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 103909-86-0 3-amino-2-butenoic acid cinnamyl ester 

Relevant articles and documents

Preparation method of 3-amino-2-butenoic acid cinnamyl ester

The invention provides a preparation method of 3-amino-2-butenoic acid cinnamyl ester, which comprises the following steps: mixing diketene with cinnamyl alcohol in a dropwise adding manner, and carrying out an esterification reaction to obtain a mixed solution containing acetoacetic acid cinnamyl ester; wherein in the process of dropwise adding the diketene, the temperature of the esterificationreaction is 30-60 DEG C. The preparation method provided by the invention is simple and feasible, the product yield is higher, the intermediate product does not need to be purified, the subsequent reaction can be directly carried out, and the method is suitable for large-scale production.

Enzymatic Synergism in the Synthesis of β-Keto Esters

Reaction of alcohols with ethyl and tert-butyl acetoacetate catalyzed by a combination of commercially available enzymes is shown to be a convenient method for the preparation of a range of acetoacetic acid derivatives. Systematic studies proved that the combination of two or more enzymes enhances the yield of the reaction. Application of the selected enzyme mixture for enzymatic transesterification of various β-keto esters provided the respective products in excellent yields up to 96% and quantitative within 24 and 48 hours, respectively. The presented methodology is simple and mild, and can be used to prepare acetoacetates from primary and secondary alcohols. Application of a selected enzyme mixture for enzyme-catalyzed esterification of various carboxylic acids provided the respective β-hydroxy esters in excellent yields up to 96% and quantitative within 24 and 48 hours, respectively.

General and efficient transesterification of β-keto esters with various alcohols using Et3N as a br?nsted base additive

Transesterification of β-keto esters with a wide variety of allyl, benzyl, propargyl, and alkyl alcohols using, for the first time, commercially available and inexpensive Et3N as a Br?nsted base additive, is efficiently performed in toluene at reflux. The corresponding esters are exclusively obtained in 57-98% yields with no trace amounts of γ,δ-ketones, usually expected from the decarboxylative Carroll rearrangement.