185693-08-7

Basic information

• Product Name: 3-AZABICYCLO[3.1.0]HEXAN-6-AMINE
• CAS NO: 185693-08-7
• Molecular Weight: 98.1478
• Mol File: 185693-08-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-AZABICYCLO[3.1.0]HEXAN-6-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AZABICYCLO[3.1.0]HEXAN-6-AMINE(185693-08-7)
• EPA Substance Registry System: 3-AZABICYCLO[3.1.0]HEXAN-6-AMINE(185693-08-7)

Safety Data

• Hazardous Substances Data: 185693-08-7(Hazardous Substances Data)

Upstream product

• 151860-16-1 (1α,5α,6α)-3-N-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane 
• 151860-15-0 (1α,5α,6α)-3-N-benzyl-6-nitro-2,4-dioxo-3-azabicyclo[3.1.0]hexane 
• 151860-17-2 (1α,5α,6α)-3-N-benzyl-6-amino-3-aza-bicyclo[3.1.0]hexane 

Downstream Products

• 288628-59-1 Ethyl (1α,5α,6α)-7-(6-benzylideneamino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 
• 146836-84-2 trovafloxacin mesylate 
• 171176-56-0 Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 

Relevant articles and documents

3-AZABICYCLO [3.1.0] HEXANE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The present invention relates to 3-azabicyclo[3.1.0]hexane derivatives, which are useful as vanilloid receptor (VR) ligands, methods of treating diseases, conditions and/or disorders modulated by vanilloid receptors with them, and processes for preparing them.

Synthesis of trovafloxacin using various (1α,5α,6α)-3-azabicyclo[3.1.0]hexane derivatives

Trovafloxacin, a novel broad spectrum antibacterial, contains the unusual (1α,5α,6α)-3-azabicyclo[3.1.0]hexane ring system. The prototype of the industrial synthesis of this ring system and possible mechanistic pathways to exclusive formation of the exo or 6α-nitro derivative 4 are described, which leads to the key 6a-nitro-3-azabicyclo[3.1.0]hexane intermediate 10. The synthesis of 6a-amino-3-azabicyclo[3.1.0]hexane 16 and useful protected cxo 6-amino derivatives 15 and 17 follows from 10. These can be coupled with the 7-chloronaphthyridone 18 to yield protected trovafloxacin compounds 20-22 in good yield. The ethyl ester of trovafloxacin 21 can also be accessed from the product of coupling 19, derived from 18 and the exo 6-nitro-3-azabicyclo[3.1.0]hexane compound 12. Removal of protecting groups from 20-22 with methanesulfonic acid yields trovafloxacin mesylate from which trovafloxacin zwitterion 1 can be liberated with base treatment. Zwitterion l can also be prepared directly from 16 tosylate salt and naphthyridone-2-carboxylic acid 26. The Royal Society of Chemistry 2000.