81840-59-7

Basic information

• Product Name: Oxirane, [[2-(2-propenyl)phenoxy]methyl]-, (2S)-
• CAS NO: 81840-59-7
• Molecular Formula: C12H14O2
• Molecular Weight: 190.242
• Mol File: 81840-59-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Oxirane, [[2-(2-propenyl)phenoxy]methyl]-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxirane, [[2-(2-propenyl)phenoxy]methyl]-, (2S)-(81840-59-7)
• EPA Substance Registry System: Oxirane, [[2-(2-propenyl)phenoxy]methyl]-, (2S)-(81840-59-7)

Safety Data

• Hazardous Substances Data: 81840-59-7(Hazardous Substances Data)

Upstream product

• 4638-04-4 1-(2-allylphenoxy)-2,3-epoxypropane 
• 1745-81-9 o-Allylphenol 
• 57044-25-4 (R)-oxiranemethanol 
• 1972-28-7 diethylazodicarboxylate 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 1314092-54-0 (2S)-glycidyl-3-nitrobenzenesulfonate 
• 141987-30-6 Acetic acid 2-(2-allyl-phenoxy)-1-chloromethyl-ethyl ester 
• 49716-04-3 1-(2-allyl-phenoxy)-3-chloro-propan-2-ol 
• 141987-49-7 (R)-1-(2-Allyl-phenoxy)-3-chloro-propan-2-ol 

Downstream Products

• 1335302-76-5 (S)-tert-butyl 2-(3-(2-allylphenoxy)-2-hydroxypropylamino)ethylcarbamate 
• 1335302-81-2 (S)-13-amino-1-(2-(prop-2-en-1-yl)phenyl)-1,8,11-trioxa-5-azatridecan-3-ol 
• 131813-62-2 N-[-(R)-1,2,3,4-tetrahydronaphth-2-yl]-(S)-2-hydroxy-3-(2-allylphenoxy)propanamine 
• 23846-71-1 (S)-alprenolol 

Relevant articles and documents

Probing the Existence of a Metastable Binding Site at the β2-Adrenergic Receptor with Homobivalent Bitopic Ligands

Herein, we report the development of bitopic ligands aimed at targeting the orthosteric binding site (OBS) and a metastable binding site (MBS) within the same receptor unit. Previous molecular dynamics studies on ligand binding to the β2-adrenergic receptor (β2AR) suggested that ligands pause at transient, less-conserved MBSs. We envisioned that MBSs can be regarded as allosteric binding sites and targeted by homobivalent bitopic ligands linking two identical pharmacophores. Such ligands were designed based on docking of the antagonist (S)-alprenolol into the OBS and an MBS and synthesized. Pharmacological characterization revealed ligands with similar potency and affinity, slightly increased β2/β1AR-selectivity, and/or substantially slower β2AR off-rates compared to (S)-alprenolol. Truncated bitopic ligands suggested the major contribution of the metastable pharmacophore to be a hydrophobic interaction with the β2AR, while the linkers alone decreased the potency of the orthosteric fragment. Altogether, the study underlines the potential of targeting MBSs for improving the pharmacological profiles of ligands.

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.

Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers. 31P NMR analysis of the enantiomeric composition of oxiranes

The enantioselective partial hydrolysis of a number of racemic aryl glycidyl ethers in the presence of chiral Co(salen)-catalyst was studied. The enantiomeric composition of the isolated (R)-aryl glycidyl ethers was analyzed by 31P NMR using optically active substituted 2-chloro-1,3,2- dioxaphospholanes. A synthesis of β-adrenoblocking agents (S)-toliprolol and (S)-moprolol based on the simultaneously obtained (S)-3-aryloxypropane-1,2- diols was proposed.