67644-21-7

Basic information

• Product Name: (+/-)-1-PHENYL-3-AZABICYCLO[3.1.0]HEXANE
• Synonyms: (+/-)-1-PHENYL-3-AZABICYCLO[3.1.0]HEXANE
• CAS NO: 67644-21-7
• Molecular Formula: C₁₁H₁₃N
• Molecular Weight: 159.23
• Mol File: 67644-21-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 255.477 °C at 760 mmHg
• Flash Point: 111.742 °C
• Appearance: /
• Density: 1.118 g/cm³
• CAS DataBase Reference: (+/-)-1-PHENYL-3-AZABICYCLO[3.1.0]HEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-1-PHENYL-3-AZABICYCLO[3.1.0]HEXANE(67644-21-7)
• EPA Substance Registry System: (+/-)-1-PHENYL-3-AZABICYCLO[3.1.0]HEXANE(67644-21-7)

Safety Data

• Hazardous Substances Data: 67644-21-7(Hazardous Substances Data)

Usage

Description

(+/-)-1-PHENYL-3-AZABICYCLO[3.1.0]HEXANE, also known as tropinone, is a bicyclic organic compound with a chemical formula C8H11N. It is a key intermediate in the synthesis of tropane alkaloids, which are commonly found in plants of the Solanaceae family and have various pharmacological properties. Tropinone possesses structural versatility and pharmacological significance, making it a valuable compound with numerous potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
(+/-)-1-PHENYL-3-AZABICYCLO[3.1.0]HEXANE is used as a precursor in the production of pharmaceuticals for its ability to be synthesized into tropane alkaloids. These alkaloids have anticholinergic and psychotropic effects, making them useful in the development of drugs targeting various medical conditions.
Used in Organic Synthesis:
(+/-)-1-PHENYL-3-AZABICYCLO[3.1.0]HEXANE is used as a chiral building block in organic synthesis due to its structural versatility. This allows for the creation of various compounds with different properties, contributing to the advancement of chemical research and development.
Used in Drug Discovery and Medicinal Chemistry:
(+/-)-1-PHENYL-3-AZABICYCLO[3.1.0]HEXANE and its derivatives have potential applications in drug discovery and medicinal chemistry. Their unique structure and properties make them promising candidates for the development of new drugs and therapeutic agents.

Upstream product

• 66503-91-1 1-phenyl-3-azabicyclo<3.1.0>hexane-2,4-dione 
• 66504-07-2 (-)-1-(p-Chlorophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane hydrochloride 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 
• 101-97-3 Ethyl 2-phenylethanoate 
• 731-05-5 cis (±)-diethyl 1-phenylcyclopropane-1,2-dicarboxylate 
• 882-72-4 cis (±)-1-phenylcyclopropane-1,2-dicarboxylic acid 

Downstream Products

• 67644-23-9 o-(1-Phenyl-3-azabicyclo[3.1.0]hex-3-ylcarbonyl)benzoic acid 
• 67644-41-1 3-acetyl-1-(p-aminophenyl)-3-azabicyclo[3.1.0]hexane 
• 67644-28-4 3-p-Nitrobenzoyl-1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane 
• 66504-30-1 3-acetyl-1-phenyl-3-azabicyclo[3.1.0]hexane 
• 67644-27-3 3-(m-fluorobenzoyl)-1-phenyl-3-azabicyclo[3.1.0]hexane 
• 67644-26-2 3-(p-fluorobenzoyl)-1-phenyl-3-azabicyclo[3.1.0]hexane 
• 66504-32-3 3-Cyclohexylcarbonyl-1-phenyl-3-azabicyclo[3.1.0]hexane 

Relevant articles and documents

Use of 1-(substitutedphenyl)-3-azabicyclo[3.1.0]hexanes for the treatment of chemical dependencies

The invention is a method of treatment for the relief of an addictive, compulsive disorder which comprises the administration to a human or animal suffering from such a disorder an effective amount of the compound of the formula: wherein R is hydrogen, alkyl (C1-C6); R1is hydrogen, mono or disubstituted halogen, alkoxy (C1-C3), CF3, alkyl (C1-C6); and R2is hydrogen, methyl or ethyl, or a pharmaceutically acceptable salt thereof.

1-Aryl-3-azabicyclohexanes, a New Series of Nonnarcotic Analgesic Agents

A series of 1-aryl-3-azabicyclohexanes was synthesized by hydride reduction of 1-arylcyclopropanedicarboximides.Hydroxyphenyl analogues 20, 22, and 24 were prepared by EtSNa-DMF ether cleavage of the corresponding methoxyphenyl analogues 2m, 2n, and 23, respectively, with the secondary amines 20 and 22 going through the N-formyl intermediates 19 and 21.The p-ethoxy analogue 26 was obtained by O-ethylation of 19, followed by base hydrolysis of the amide 25.The greatest analgesic potency in mouse writhing and rat paw-pain assays was observed for para-substituted compounds.Bicifadine, 1-(4-methylphenyl)-3-azabicyclohexane (2b), was the most potent member of the series and is presently undergoing clinical trials in man.Analgesic activity of 2b is limited to the (+) enantiomer 2v, which has the 1R,5S absolute configuration as determined by single-crystal X-ray analysis.The N-methyl analogue (27d) of 2b showed significant analgesic potency, whereas the N-allyl (27a), N-(cyclopropylmethyl) (27b), and N-(n-hexyl) (27c) analogues were inactive.Bicifadine (2b) showed a nonnarcotic profile different from analogous azabicycloalkane and 3-phenylpyrrolidine analgesics.

Acylazabicyclohexanes

Phenyl and substituted phenyl 3-azabicyclo[3.1.0]-hexanes and method of preparing the same are described. They are useful as intermediates in preparing other physiologically active compounds.