6134-71-0

Basic information

• Product Name: α-Butyl-β-oxobenzenepropionic acid ethyl ester
• Synonyms: 2-Benzoylhexanoic acid ethyl ester;α-Butyl-β-oxobenzenepropanoic acid ethyl ester;α-Butyl-β-oxobenzenepropionic acid ethyl ester
• CAS NO: 6134-71-0
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.3175
• Mol File: 6134-71-0.mol

Chemical Properties

• Boiling Point: 329.2°Cat760mmHg
• Flash Point: 140.7°C
• Appearance: /
• Density: 1.033g/cm³
• Vapor Pressure: 0.00018mmHg at 25°C
• Refractive Index: 1.497
• PKA: 11.27±0.26(Predicted)
• CAS DataBase Reference: α-Butyl-β-oxobenzenepropionic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: α-Butyl-β-oxobenzenepropionic acid ethyl ester(6134-71-0)
• EPA Substance Registry System: α-Butyl-β-oxobenzenepropionic acid ethyl ester(6134-71-0)

Safety Data

• Hazardous Substances Data: 6134-71-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H20O3/c1-3-5-11-13(15(17)18-4-2)14(16)12-9-7-6-8-10-12/h6-10,13H,3-5,11H2,1-2H3

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 122-56-5 tributyl borane 
• 100-47-0 benzonitrile 
• 2414-98-4 magnesium ethylate 
• 100-44-7 benzyl chloride 
• 7391-39-1 ethyl 2-cyanohexanoate 
• 98-80-6 phenylboronic acid 
• 65-85-0 benzoic acid 
• 123-66-0 Ethyl hexanoate 
• 93-89-0 benzoic acid ethyl ester 
• 1009-14-9 phenyl butyl ketone 

Downstream Products

• 7377-47-1 2-amino-5-butyl-6-phenyl-3H-pyrimidin-4-one 
• 942-92-7 caprophenone 
• 1395343-42-6 5-butyl-4-(4-methoxyphenyl)-6-phenylpyrimidin-2-amine 
• 1395343-15-3 2-amino-5-butyl-4-chloro-6-phenylpyrimidine 
• 7377-47-1 2-amino-5-butyl-6-phenylpyrimidin-4-ol 

Relevant articles and documents

Synthetic Scope of Br?nsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate

The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Br?nsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl-methyl ketones produced only aryl-migrated products, whereas other ketones yielded a mixture of products. For diaryl ketones, the identity of two inseparable migrated products was confirmed by two-dimensional NMR spectroscopy.

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

Palladium catalyzed decarboxylative acylation of arylboronic acid with ethyl cyanoacetate as a new acylating agent: Synthesis of alkyl aryl ketones

Palladium catalyzed acylation of arylboronic acid containing various functional groups was performed efficiently by ethyl cyanoacetate/substituted ethyl cyanoacetate as the acylating agent in aqueous triflic acid medium. The alkyl aryl ketones were obtained in good to excellent yields, first by addition of arylboronic acid to the nitrile group of ethyl cyanoacetate and their derivatives, followed by in situ decarboxylation of the resulting β-ketoester.

A simple and efficient transformation of fischer carbene complexes into bromomethyl ketones or β-ketoesters

Fischer-type carbene complexes react via nucleophilic attack with dibromomethyllithium or haloester lithium enolates to afford bromomethyl ketones or β-ketoesters, respectively.