1369768-29-5

Basic information

• Product Name: [(1R,2S)-2-(3-fluorophenyl)-2-(hydroxymethyl)cyclopropyl]-methyl acetate
• Synonyms: [(1R,2S)-2-(3-fluorophenyl)-2-(hydroxymethyl)cyclopropyl]-methyl acetate
• CAS NO: 1369768-29-5
• Molecular Weight: 238.259
• Mol File: 1369768-29-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: [(1R,2S)-2-(3-fluorophenyl)-2-(hydroxymethyl)cyclopropyl]-methyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: [(1R,2S)-2-(3-fluorophenyl)-2-(hydroxymethyl)cyclopropyl]-methyl acetate(1369768-29-5)
• EPA Substance Registry System: [(1R,2S)-2-(3-fluorophenyl)-2-(hydroxymethyl)cyclopropyl]-methyl acetate(1369768-29-5)

Safety Data

• Hazardous Substances Data: 1369768-29-5(Hazardous Substances Data)

Usage

General Description

The chemical "[(1R,2S)-2-(3-fluorophenyl)-2-(hydroxymethyl)cyclopropyl]-methyl acetate" is a complex compound with a cyclopropyl-methyl acetate structure. It contains a fluorophenyl group and a hydroxymethyl group within the cyclopropyl ring. The compound is a chiral molecule with one stereogenic center, resulting in two enantiomers (1R,2S) and (1S,2R). It may have potential applications in pharmaceuticals or agrochemicals due to its unique structural and chiral properties, which can influence its biological activities. The chemical may also have uses in material science and other industrial applications due to its diverse and complex structure.

Upstream product

• 501-00-8 3-fluorophenylacetonitrile 
• 108-05-4 vinyl acetate 
• 1369767-20-3 ((1S,2R)-1-(3-fluorophenyl)cyclopropane-1,2-diyl)dimethanol 
• 528587-70-4 (1S,5R)-2-oxo-1-(3-fluorophenyl)-3-oxabicyclo[3.1.0]hexane 
• 1450904-98-9 (1S,2R)-1-(3-fluorophenyl)-2-(hydroxymethyl)cyclopropane-1-carbonitrile 
• 1450905-00-6 (1S,2R)-1-(3-fluorophenyl)-2-(hydroxymethyl)cyclopropane-1-carboxylic acid 

Downstream Products

• 1450904-94-5 C₁₉H₂₁FN₂O₃ 
• 1369767-24-7 ((1R,2S)-2-(((2,4-dimethylpyrimidin-5-yl)oxy)methyl)-2-(3-fluorophenyl)cyclopropyl)methanol 
• 1369767-26-9 (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)cyclopropanecarbaldehyde 
• 1369769-35-6 (1R,2S)-2-(((2,4-dimethylpyrimidin-5-yl)oxy)methyl)-2-(3-fluorophenyl)cyclopropanecarboxylic acid 
• 1369764-02-2 (1R,2S)-2-[{(2,4-dimethylpyrimidin-5-yl)oxy}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide 
• 1450904-92-3 ((1R,2S)-2-(3-fluorophenyl)-2-((p-tosyloxy)methyl)cyclopropyl)methyl acetate 
• 1369764-01-1 (1R,2S)-2-(((2,4-dimethylpyrimidin-5-yl)oxy)methyl)-N-(5-fluoro-4-methoxypyridin-2-yl)-2-(3-fluorophenyl)cyclopropanecarboxamide 
• 1369768-06-8 C₁₈H₁₉FN₂O₄ 
• 1449429-88-2 C₁₈H₂₀FN₃O₃ 
• 1369764-98-6 (1R,2S)-2-(((2-methyl-4-methoxymethylpyrimidin-5-yl)oxy)methyl)-N-(5-fluoropyridin-2-yl)-2-(3-fluorophenyl)cyclopropanecarboxamide 
• 1369765-96-7 (1R,2S)-2-(((2-methyl-4-hydroxymethylpyrimidin-5-yl)oxy)-methyl)-N-(5-fluoropyridin-2-yl)-2-(3-fluorophenyl)-cyclopropanecarboxamide 
• 1369769-04-9 C₁₇H₁₈FN₃O₂ 
• 1369766-53-9 (1R,2S)-2-(((2,4-dimethylpyrimidin-5-yl)oxy)methyl)-2-(3-fluorophenyl)-N-(5-fluoro-6-hydroxypyridin-2-yl)cyclopropanecarboxamide 
• 1369765-88-7 (1R,2S)-2-(((2,4-dimethylpyrimidin-5-yl)oxy)methyl)-2-(3-fluorophenyl)-N-(5-iodopyridin-2-yl)cyclopropanecarboxamide 

Relevant articles and documents

Discovery of (1R,2S)-2-{[(2,4-Dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide (E2006): A Potent and Efficacious Oral Orexin Receptor Antagonist

The orexin/hypocretin receptors are a family of G protein-coupled receptors and consist of orexin-1 (OX1) and orexin-2 (OX2) receptor subtypes. Orexin receptors are expressed throughout the central nervous system and are involved in the regulation of the sleep/wake cycle. Because modulation of these receptors constitutes a promising target for novel treatments of disorders associated with the control of sleep and wakefulness, such as insomnia, the development of orexin receptor antagonists has emerged as an important focus in drug discovery research. Here, we report the design, synthesis, characterization, and structure-activity relationships (SARs) of novel orexin receptor antagonists. Various modifications made to the core structure of a previously developed compound (-)-5, the lead molecule, resulted in compounds with improved chemical and pharmacological profiles. The investigation afforded a potential therapeutic agent, (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide (E2006), an orally active, potent orexin antagonist. The efficacy was demonstrated in mice in an in vivo study by using sleep parameter measurements. (Chemical Equation Presented).

METHODS AND COMPOUNDS USEFUL IN THE SYNTHESIS OF OREXIN-2 RECEPTOR ANTAGONISTS

The present disclosure provides compounds and methods that are useful for the preparation of compounds useful as orexin-2 receptor antagonists.