6452-72-8

Usage

Chemical Properties

Yellow Oil

Uses

An intermediate in the preparation of a β-Adrenergic blocker.

InChI:InChI=1/C12H14O3/c1-2-7-13-11-5-3-4-6-12(11)15-9-10-8-14-10/h2-6,10H,1,7-9H2

Upstream product

• 120-80-9 benzene-1,2-diol 
• 118712-54-2 glycidyl p-toluenesulfonate 
• 1126-20-1 2-allyloxyphenol 
• 106-89-8 epichlorohydrin 

Downstream Products

• 101532-61-0 5-{[3-(2-Allyloxy-phenoxy)-2-hydroxy-propyl]-methyl-amino}-2-(3,4-dimethoxy-phenyl)-2-isopropyl-pentanenitrile 
• 58827-33-1 Furan-2-carboxylic acid {2-[3-(2-allyloxy-phenoxy)-2-hydroxy-propylamino]-ethyl}-amide 
• 6452-54-6 3--1,2-propanediol 
• 90195-21-4 3-[2-(1,4,7,10-Tetraoxa-cyclododec-2-ylmethoxy)-phenoxy]-propane-1,2-diol 
• 90195-22-5 3-[2-(1,4,7,10,13-Pentaoxa-cyclopentadec-2-ylmethoxy)-phenoxy]-propane-1,2-diol 
• 90195-23-6 3-[2-(1,4,7,10,13,16-Hexaoxa-cyclooctadec-2-ylmethoxy)-phenoxy]-propane-1,2-diol 
• 90195-24-7 Toluene-4-sulfonic acid 2-hydroxy-3-[2-(1,4,7,10-tetraoxa-cyclododec-2-ylmethoxy)-phenoxy]-propyl ester 
• 90195-25-8 Toluene-4-sulfonic acid 2-hydroxy-3-[2-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-phenoxy]-propyl ester 
• 90195-26-9 Toluene-4-sulfonic acid 3-[2-(1,4,7,10,13,16-hexaoxa-cyclooctadec-2-ylmethoxy)-phenoxy]-2-hydroxy-propyl ester 
• 90219-07-1 <<2-(allyloxy)phenoxy>methyl>-12-crown-4 
• 345661-32-7 <<2-(2,3-epoxypropyloxy)phenoxy>methyl>-12-crown-4 
• 90219-08-2 <<2-(allyloxy)phenoxy>methyl>-15-crown-5 
• 344575-20-8 2-(2-Oxiranylmethoxy-phenoxymethyl)-1,4,7,10,13-pentaoxa-cyclopentadecane 
• 90195-17-8 <<2-(allyloxy)phenoxy>methyl>-18-crown-6 

Relevant academic research and scientific papers

A smart library of epoxide hydrolase variants and the top hits for synthesis of (S)-β-blocker precursors

Microtuning of the enzyme active pocket has led to a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β-blocker precursors. Improved activities of 6- to 430-fold were achieved by redesigning the active site at two predicted hot spots. This study represents a breakthrough in protein engineering of epoxide hydrolases and resulted in enhanced activity toward bulky substrates. Hot pockets: Microtuning of the enzyme active pocket gives a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β-blocker precursors. Improved activities of 6- to 430-fold were achieved by redesigning the active site at two predicted hot spots, and enhanced activity toward bulky substrates was found.

Propanolamine derivatives

This invention relates to new propanolamine derivatives presented by the following formula [I]: wherein R1 is hydrogen or lower alkenyloxy, R2 is carboxy(lower)alkoxy or protected carboxy(lower)alkoxy, R3 is hydrogen or N-protective group, n is an integer of 1 or 2, and salts thereof which have gut selective sympathomimetic, anti-ulcerous, anti-pancreatitis, lipolytic and anti-pollakisuria activities, to processes for the preparation thereof and to a pharmaceutical composition comprising the same.

Determination of the enantiomeric purity and the configuration of β- aminoalcohols using (R)-2-fluorophenylacetic acid (AFPA) and fluorine-19 NMR: Application to β-blockers

A method has been developed for determining the enantiomeric purity and the absolute configuration of β-aminoalcohols of type ArOCH2CH(OH)CH2NHR (R = iPr, tBu). To determine enantiomeric purity, the amine function was first protected by a benzyl group, then the compound formed was esterified using the acid chloride of (R)-2-fluorophenylacetic acid (AFPA). The 19F NMR analysis of the derivative obtained revealed the presence of two distinctly separate signals (~2.5 ppm), the one for the RS-SR pair being the most deshielded. The configuration was determined directly on the aminoalcohol by using the acid. In stoichiometric conditions, when R = iPr, the amide function was obtained very preponderantly. The 19F NMR spectrum of the amide presented four distinct signals when derivatization was carried out by means of a reaction between the (±)-β-aminoalcohol and the (R)-AFPA. The extreme signals, which were over 3.5 ppm apart, did not belong to the same diastereomer. With R = tBu essentially the ester function was obtained. The first studies revealed the presence of two signals, though not as clearly separated as in the previous cases. Each experiment was simple to perform, and purification was not necessary. Mosher's acid gave unsatisfactory results in each case. (C) 2000 Elsevier Science Ltd.

Synthesis and Binding Studies of Crown Ethers Bearing Pharmacophoric Groups: Epoxy Lariat Crown Ethers

A series of lariat ethers (derivatives of 18-crown-6, 15-crown-5, and 12-crown-4) bearing pendant epoxy groups has been prepared and the homogeneous stability (binding) constants (Ks) with Na+ and K+ in MeOH have been measured.The epoxy groups appear to have only a marginal influence on complexation of K+ in the larger ring compounds and do not enhance Na+ binding.These epoxy lariat ethers exhibit no in vivo activity against P388 mouse leukemia at dose levels of 128 mg/kg and below.