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

General Description

The chemical (+/-)-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 can be used as a precursor in the production of pharmaceuticals, including drugs with anticholinergic and psychotropic effects. It is also used as a chiral building block in organic synthesis, and its derivatives have potential applications in drug discovery and medicinal chemistry. Due to its structural versatility and pharmacological significance, tropinone is a valuable compound with numerous potential applications in various fields.

Upstream product

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

Downstream Products

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