66966-19-6

Usage

Uses

Used in Chemical Synthesis:
(2R)-3-(O-allyloxphenoxy)-1,2-epoxypropane is utilized as a key intermediate in the synthesis of various chemical products due to its reactivity and the presence of the epoxide and allyloxy groups. This allows for the creation of a broad spectrum of compounds, including polymers, resins, and pharmaceuticals, which are essential in multiple industries.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, (2R)-3-(O-allyloxphenoxy)-1,2-epoxypropane serves as a crucial building block for the development of new drugs. Its unique structure and reactivity enable the synthesis of complex molecules with potential therapeutic applications.
Used in Polymer and Resin Production:
(2R)-3-(O-allyloxphenoxy)-1,2-epoxypropane is employed as a reactive monomer in the production of polymers and resins. Its incorporation into these materials can enhance properties such as strength, flexibility, and chemical resistance, making them suitable for a variety of applications, including coatings, adhesives, and composite materials.
Used in Industrial Applications:
Across different industries, (2R)-3-(O-allyloxphenoxy)-1,2-epoxypropane is used for its versatility and reactivity in chemical transformations. This allows for the development of innovative products and processes that can improve efficiency, performance, and sustainability in various sectors.

Upstream product

• 118712-54-2 glycidyl p-toluenesulfonate 
• 1126-20-1 2-allyloxyphenol 
• 120-80-9 benzene-1,2-diol 
• 70987-78-9 (S)-Glycidyl tosylate 
• 6452-72-8 1-(2-allyloxyphenoxy)-2,3-epoxypropane 
• 115314-14-2 (R)-glycidyl nosylate 
• 429-41-4 tetrabutyl ammonium fluoride 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 118712-60-0 S-oxiran-2-ylmethyl 4-nitrobenzenesulfonate 
• 6452-74-0 3-(o-Allyloxyphenoxy)-2-hydroxy-1-chlorpropan 
• 141987-51-1 (R)-3-(2-allyloxy phenoxy)-1-chloro-2-propanol 
• 106-89-8 epichlorohydrin 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 141987-34-0 Acetic acid 2-(2-allyloxy-phenoxy)-1-chloromethyl-ethyl ester 

Downstream Products

• 53672-27-8 N-{2-[3-(2-Allyloxy-phenoxy)-2-hydroxy-propylamino]-ethyl}-isobutyramide 
• 59613-89-7 1-(2-Allyloxy-phenoxy)-3-{6-[3-(2-allyloxy-phenoxy)-2-hydroxy-propylamino]-hexylamino}-propan-2-ol 
• 66901-82-4 (R)-2-allyloxy-1-(2,3-dihydroxypropoxy)benzene 
• 66817-28-5 N-({2-[3-(2-Allyloxy-phenoxy)-2-hydroxy-propylamino]-ethylcarbamoyl}-methyl)-4-chloro-benzamide 
• 66825-06-7 1-(2-Allyloxy-phenoxy)-3-(2-amino-ethylamino)-propan-2-ol 

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.

PROCESS FOR PRODUCING GLYCIDYL ETHER

A process for producing a glycidyl ether and an optically active compound thereof with high yield and an optically high purity comprising reacting an alcohol with epihalohydrin in a base to thereby produce a glycidyl ether, the reaction performed in a two-layer system of a nonaqueous organic solvent and an aqueous solvent.

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.

Process for preparation of glycidyl ether

PCT No. PCT/JP97/03221 Sec. 371 Date Apr. 29, 1999 Sec. 102(e) Date Apr. 29, 1999 PCT Filed Sep. 12, 1997 PCT Pub. No. WO98/12186 PCT Pub. Date Mar. 26, 1998A process for preparation of a glycidyl ether which is characrelized in reacting an epoxy compound of the formula wherein X is halogen or sulfonyloxy in the presence of a fluoride salt, with an alcohol. According to the above method, glycigyl ethers or their optically active compounds important as intermediates for synthesis of medicines are easily obtained in good yield and especially the optically active compounds are obtained with highly optical purity.

Process for the preparation of 3-amino-2-hydroxy-1-propyl ethers

PCT No. PCT/JP97/03220 Sec. 371 Date Apr. 28, 1999 Sec. 102(e) Date Apr. 28, 1999 PCT Filed Sep. 12, 1997 PCT Pub. No. WO98/12171 PCT Pub. Date Mar. 26, 1998A process for preparation of 3-amino-2-hydroxy-1-propyl ether of the formula wherein R1 is substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic ring, R2 and R3 are the same or different hydrogen atom, a substituted or unsubstituted alkyl, or may form a ring together with an adjacent nitrogen atom, which ring may be interrupted with nitrogen atom, oxygen atom or sulfur atom, which is characterized in reacting an epoxy compound of the formula wherein X is halogen, in the presence of a fluoride salt, with an alcohol and then reacting an amine. According to the above method, an intermediates for synthesis of medicines is obtained in good yield and highly optical purity.

CsF in organic synthesis. Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure β-blockers

The two modes of the paths in the reaction of oxiranes with phenols are completely controlled by CsF. Glycidyl nosylate undergoes exclusive substitution at the C1 position whereas the ring-opening (C-3 attack) occurs with epichlorohydrin, glycidol, and 1,2-epoxyalkanes. These reactions provide convenient access to enantiopure β-blockers.

CsF in organic synthesis. The first and convenient synthesis of enantiopure bisoprolol by use of glycidyl nosylate

The regioselective substitution of glycidyl nosylate with phenols is catalyzed by CsF in the presence of K2CO3 in DMF; this reaction enables the first and convenient synthesis of enantiopure bisoprolol.

Enzyme Assisted Preparation of Enantiomerically Pure β-Adrenergic Blockers III. Optically Active Chlorohydrin Derivatives and Their Conversion

Optical active chlorohydrin derivatives 2a-m and 3a-m of both enantiomeric series were prepared via both enzymatic hydrolyses and acyltransfer reactions catalysed by a highly selective lipase from Pseudomonas sp..The resulting building blocks were further transformed into the corresponding β-blockers of high enantiomeric purity.

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.