3466-82-8

Basic information

• Product Name: 2-PHENYL-AZEPANE
• Synonyms: Hexahydro-2-phenyl-1H-azepine;2-Phenylhexahydroazepine;2-Phenylperhydroazepine;2-phenylazacycloheptane;2-Phenyl-hexaMethyleniMine;1H-Azepine,hexahydro-2-phenyl-;2-PHENYL-AZEPANE
• CAS NO: 3466-82-8
• Molecular Formula: C₁₂H₁₇N
• Molecular Weight: 175.27
• Product Categories: Aromatics;Heterocycles
• Mol File: 3466-82-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 277℃
• Flash Point: 123℃
• Appearance: /
• Density: 0.950
• Vapor Pressure: 0.00502mmHg at 25°C
• Refractive Index: 1.499
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2-PHENYL-AZEPANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-AZEPANE(3466-82-8)
• EPA Substance Registry System: 2-PHENYL-AZEPANE(3466-82-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 3466-82-8(Hazardous Substances Data)

Usage

Description

2-Phenylazepane is a heterocyclic compound with a seven-membered azepane ring and a phenyl group attached to the second carbon. It serves as a key intermediate in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
2-Phenylazepane is used as a key intermediate in the synthesis of pyrrolylphenylsulfonates, which act as dopamine D3 antagonists. These antagonists are important in the development of medications for the treatment of various central nervous system disorders, such as schizophrenia and other dopamine-related conditions.
Additionally, 2-phenylazepane is used in the preparation of substituted amidothiophene derivatives, which serve as 11-β-HSD1 inhibitors. These inhibitors play a crucial role in the regulation of glucocorticoid levels, making them potential candidates for the treatment of metabolic and inflammatory diseases, such as type 2 diabetes and obesity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 7627, 1993 DOI: 10.1021/jo00079a001Synthetic Communications, 25, p. 3789, 1995 DOI: 10.1080/00397919508011452

InChI:InChI=1/C12H16FN/c13-11-7-5-10(6-8-11)12-4-2-1-3-9-14-12/h5-8,12,14H,1-4,9H2

Upstream product

• 3338-00-9 2-phenyl-4,5,6,7-tetrahydro-3H-azepine 
• 111-49-9 hexamethylene imine 
• 591-51-5 phenyllithium 
• 24740-68-9 7-chloro-2,3,4,5-tetrahydro-1H-azepine-1-carbaldehyde 
• 1542147-52-3 C₁₃H₁₅NO 
• 39510-50-4 6-amino-1-phenylhexan-1-one 
• 128372-99-6 (6-oxo-6-phenyl-hexyl)-carbamic acid tert-butyl ester 
• 106412-36-6 tert-butyl 2-oxoazepane-1-carboxylate 
• 105-60-2 caprolactam 
• 80053-69-6 cyclohexanone oxime methanesulfonate 
• 87876-93-5 cyclohexanone O-(ethoxycarbonyl)oxime 

Relevant articles and documents

Direct access to functionalized azepanes by cross-coupling with α-halo eneformamides

The synthesis of functionalized azepanes was accomplished through the palladium-mediated cross-coupling of α-halo eneformamides with mostly unactivated nucleophiles under mild conditions. Alkenylations proceeded with excellent stereoselectivitiy. In most

Chemoenzymatic Synthesis of Substituted Azepanes by Sequential Biocatalytic Reduction and Organolithium-Mediated Rearrangement

Enantioenriched 2-aryl azepanes and 2-arylbenzazepines were generated biocatalytically by asymmetric reductive amination using imine reductases or by deracemization using monoamine oxidases. The amines were converted to the corresponding N′-aryl ureas, which rearranged on treatment with base with stereospecific transfer of the aryl substituent to the 2-position of the heterocycle via a configurationally stable benzyllithium intermediate. The products are previously inaccessible enantioenriched 2,2-disubstituted azepanes and benzazepines.

A One-Pot Process for the Enantioselective Synthesis of Amines via Reductive Amination under Transfer Hydrogenation Conditions

(Equation presented) Cyclic amines may be prepared via a sequence of deprotection followed by intramolecular reductive amination of t-Boc-protected amino ketones under asymmetric transfer hydrogenation conditions. In cases where the corresponding imine reaction proceeds with high enantioselectivity, this is reflected in the one-step process.