528587-70-4

Basic information

• Product Name: (1S,5R)-2-oxo-1-(3-fluorophenyl)-3-oxabicyclo[3.1.0]hexane
• Synonyms: (1S,5R)-2-oxo-1-(3-fluorophenyl)-3-oxabicyclo[3.1.0]hexane
• CAS NO: 528587-70-4
• Molecular Weight: 192.19
• Mol File: 528587-70-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 344.8±35.0 °C(Predicted)
• Density: 1.390±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (1S,5R)-2-oxo-1-(3-fluorophenyl)-3-oxabicyclo[3.1.0]hexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,5R)-2-oxo-1-(3-fluorophenyl)-3-oxabicyclo[3.1.0]hexane(528587-70-4)
• EPA Substance Registry System: (1S,5R)-2-oxo-1-(3-fluorophenyl)-3-oxabicyclo[3.1.0]hexane(528587-70-4)

Safety Data

• Hazardous Substances Data: 528587-70-4(Hazardous Substances Data)

Usage

General Description

The chemical (1S,5R)-2-oxo-1-(3-fluorophenyl)-3-oxabicyclo[3.1.0]hexane is a bicyclic compound with a molecular structure containing a five-membered oxygen-containing ring fused with a three-membered carbocyclic ring. The compound also features a fluorophenyl group and a ketone functional group. This chemical has potential utility in organic synthesis and medicinal chemistry due to its unique structure and reactivity. It may also have applications in pharmaceutical research and drug discovery. Additionally, its stereochemistry (1S,5R) indicates the specific configuration of the stereocenters in the molecule, which is important for understanding its properties and potential biological activity.

Upstream product

• 51594-55-9 (R)-(-)-epichlorohydrin 
• 501-00-8 3-fluorophenylacetonitrile 
• 1450905-00-6 (1S,2R)-1-(3-fluorophenyl)-2-(hydroxymethyl)cyclopropane-1-carboxylic acid 
• 1450904-98-9 (1S,2R)-1-(3-fluorophenyl)-2-(hydroxymethyl)cyclopropane-1-carbonitrile 

Downstream Products

• 528587-78-2 (1S,2R)-1-(3-fluorophenyl)-2-(hydroxymethyl)-N,N-diethylcyclopropanecarboxamide 
• 528588-18-3 (1S,4S,5R)-2-oxo-4-ethyl-1-(3-fluorophenyl)-3-oxabicyclo[3.1.0]hexane 
• 528587-86-2 (1S,2R)-1-(3-fluorophenyl)-2-formyl-N,N-diethylcyclopropanecarboxamide 
• 528587-94-2 (1S,2R)-1-(3-fluorophenyl)-2-[(S)-1-hydroxypropyl]-N,N-diethylcyclopropanecarboxamide 
• 528588-02-5 (1S,2R)-1-(3-fluorophenyl)-2-[(S)-1-azidopropyl]-N,N-diethylcyclopropanecarboxamide 
• 1369767-20-3 ((1S,2R)-1-(3-fluorophenyl)cyclopropane-1,2-diyl)dimethanol 
• 1383747-14-5 (1R,2S)-2-[(1-ethyl-3-methyl-1H-pyrazol-4-yl)oxymethyl]-2-(3-fluorophenyl)cyclopropanecarboxylic acid 
• 1383747-11-2 4-{[(1S,2R)-2-(tert-Butyldiphenylsilyloxymethyl)-1-(3-fluorophenyl)cyclopropyl]methoxy}-1-ethyl-3-methyl-1H-pyrazole 
• 1383747-12-3 {(1R,2S)-2-[(1-Ethyl-3-methyl-1H-pyrazol-4-yl)oxymethyl]-2-(3-fluorophenyl)cyclopropyl}methanol 
• 1383747-13-4 (1R,2 S)-2-[(1-Ethyl-3-methyl-1H-pyrazol-4-yl)oxymethyl]-2-(3-fluorophenyl)cyclopropanecarbaldehyde 
• 1369768-29-5 [(1R,2S)-2-(3-fluorophenyl)-2-(hydroxymethyl)cyclopropyl]-methyl acetate 
• 1369768-30-8 C₁₅H₁₇FO₄ 
• 1450904-92-3 ((1R,2S)-2-(3-fluorophenyl)-2-((p-tosyloxy)methyl)cyclopropyl)methyl acetate 
• 1450904-94-5 C₁₉H₂₁FN₂O₃ 

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.

Identification of 1S,2R-milnacipran analogs as potent norepinephrine and serotonin transporter inhibitors

A series of milnacipran analogs were synthesized and studied as monoamine transporter inhibitors, and several potent compounds with moderate lipophilicity were identified from the 1S,2R-isomers. Thus, 15l exhibited IC50 values of 1.7 nM at NET and 25 nM at SERT, which were, respectively, 20- and 13-fold more potent than 1S,2R-milnacipran 1-II.