Benzyl acetoacetate - CAS 5396-89-4
Catalog number: 5396-89-4
Category: Main Product
Molecular Formula:
Molecular Weight:
clear colorless to yellow liquid
3-oxo-butanoicaciphenylmethylester; Benzyl 3-oxobutanoate; Benzyl acetylacetate; Benzyl3-oxobutanoate; Butanoicacid,3-oxo-,phenylmethylester; FEMA 2136; BENZYL ACETOACETATE; BENZYL2-OXOBUTANOATE
Boiling Point:
298.3ºC at 760 mmHg
Cheng Q1, Wang QF, Liu LS, Zhang JL. Acta Crystallogr Sect E Struct Rep Online. 2009 Nov 14;65(Pt 12):o3074. doi: 10.1107/S160053680904714X.
The title compound, C(13)H(14)N(2)O(2), an isoxazol-5-one derivative, was synthesized by a one-pot, three-component condensation reaction of methyl acetoacetate, hydroxy-lamine hydro-chloride and 4-(dimethyl-amino)benzaldehyde. All the non-H atoms are co-planar [r.m.s deviation = 0.0039 Å], with a Z configuration about the C=C bond. The dihedral angle between the phenyl ring and the isoxazole ring is 2.58 (19)°.
2.Whole cells in enantioselective reduction of benzyl acetoacetate.
Ribeiro JB1, Ramos Ade S2, Lopes Rde O1, da Silva GV1, de Souza RO1. Braz J Microbiol. 2014 Oct 9;45(3):929-32. eCollection 2014.
The β-ketoester benzyl acetoacetate was enantioselectively reduced to benzyl (S)-3-hydroxybutanoate by seven microorganism species. The best result using free cells was obtained with the yeast Hansenula sp., which furnished 97% ee and 85% of conversion within 24 h. After immobilization in calcium alginate spheres, K.marxianus showed to be more stable after 2 cycles of reaction.
3.Design and Synthesis of Coumarin Derivatives as Novel PI3K Inhibitors.
Chen-Chen M, Liu ZP1. Anticancer Agents Med Chem. 2016 Feb 23. [Epub ahead of print]
A variety of coumarin derivatives possessing the pyridinylurea units were designed to increase their potency and isoform selectivity against PI3Ks. These novel coumarins 4a-m were prepared from 5-methyl-pyridin-2-ylamine in a straightforward way via the protection of the amino by Boc groups, benzyl bromination, ethyl acetoacetate alkylation with the generated bromomethyl pyridine, Pechmann coumarin core construction, and ureas formation by the coupling of amine 3 with a variety of aryl isocyanates. When the alkylated acetoacetate 2 was reacted with resorcinol in concentrated sulfuric acid, a cascade reaction occurred that included the Pechmann cyclization to form the coumarin core, removal of the N-Boc protective groups to generate a tert-butyl carbocation, and the Friedel-Crafts tert-butylation of the phenol ring. In general, these coumarin analogs exhibited good in vitro growth inhibitory activities against tumor K562, Hela, A549 and MCF-7 cells.
4.Synthesis, antimicrobial and anti-cancer activities of some new N-ethyl, N-benzyl and N-benzoyl-3-indolyl heterocycles.
El-Sawy ER1, Mandour AH, Mahmoud K, Islam IE, Abo-Salem HM. Acta Pharm. 2012 Jun;62(2):157-79. doi: 10.2478/v10007-012-0020-3.
A series of 1-(N-substituted-1H-indol-3-yl)-3-arylprop-2-ene-1-ones (2a, b-4a, b) were prepared and allowed to react with urea, thiourea or guanidine to give pyrimidine derivatives 5a, b-13a, b. Reaction of 2a, b-4a, b with ethyl acetoacetate in the presence of a base gave cyclohexanone derivatives 14a, b-16a, b. Reaction of the latter compounds with hydrazine hydrate afforded indazole derivatives 17a, b-19a, b. On the other hand, reaction of 2a, b-4a, b with some hydrazine derivatives, namely hydrazine hydrate, acetyl hydrazine, phenylhydrazine and benzylhydrazine hydrochloride, led to the formation of pyrazole derivatives 20a, b-31a, b. Moreover, reaction of 2a, b-4a, b with hydroxylamine hydrochloride gave isoxazole derivatives 32a, b-34a, b. The newly synthesized compounds were tested for their antimicrobial activity and showed that 4-(N-ethyl-1H-indol-3-yl)-6-(p-chlorophenyl)-pyrimidine-2-amine (11b) was the most active of all the test compounds towards Candida albicans compared to the reference drug cycloheximide.
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