280-38-6

Basic information

• Product Name: 2-azabicyclo[2.2.2]octane
• Synonyms: 2-azabicyclo[2.2.2]octane;Isoquinuclidine;2-azabicyclo[2.2.2]octane ,Isoquinuclidine;3-Azabicyclo[2.2.2]octane
• CAS NO: 280-38-6
• Molecular Formula: C₇H₁₃N
• Molecular Weight: 111.19
• Mol File: 280-38-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 174 °C
• Boiling Point: 168.9°Cat760mmHg
• Flash Point: 47.5°C
• Appearance: /
• Density: 0.934g/cm³
• Vapor Pressure: 1.58mmHg at 25°C
• Refractive Index: 1.478
• PKA: 11.62±0.20(Predicted)
• CAS DataBase Reference: 2-azabicyclo[2.2.2]octane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-azabicyclo[2.2.2]octane(280-38-6)
• EPA Substance Registry System: 2-azabicyclo[2.2.2]octane(280-38-6)

Safety Data

• Hazardous Substances Data: 280-38-6(Hazardous Substances Data)

Usage

General Description

2-Azabicyclo[2.2.2]octane is a chemical compound, easily recognizable by its bicyclic framework that consists of two three-membered ring units bridged by a nitrogen atom. This alkaline organic molecule has the molecular formula C7H13N, holds Expanded Octet properties, and has significant importance in the field of organic chemistry. The bicyclic structure of 2-azabicyclo[2.2.2] octane provides distinctive reactivity and makes it an in-demand molecule for synthetic purposes. It is commonly used as a building block in the synthesis of complex natural products and pharmaceuticals due to its highly rigid nature and the sufficient number of functionalizable sites. The 2-azabicyclo[2.2.2]octane ring structure is known for its high stability which makes it a particularly interesting target for synthetic chemists.

InChI:InChI=1/C7H13N/c1-3-7-4-2-6(1)5-8-7/h6-8H,1-5H2

Upstream product

• 46410-64-4 2-benzyl-2-aza-bicyclo[2.2.2]octane 
• 62456-15-9 methyl (1s,4s)-4-aminocyclohexane-1-carboxylate 
• 3685-23-2 cis-4-aminocyclohexane-1-carboxylic acid 
• 74403-57-9 2-benzyl-2-aza-bicyclo[2.2.2]octan-3-one 
• 1776-53-0 4-aminocyclohexanecarboxylic acid 
• 3306-69-2 2-aza-bicyclo[2.2.2]octan-3-one 

Downstream Products

• 21744-12-7 2-Nitrosoisoquinuclidine 
• 255863-81-1 (2S)-2-[5-[2-(2-azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-N-(2-pyridin-4-ylethyl)propan-1-amine 
• 24489-23-4 2-aza-bicyclo[2.2.2]octane-2-carboxylic acid 4-[2-(5-methyl-isoxazole-3-carbonylamino)-ethyl]-benzenesulfonylamide 
• 3693-57-0 2-benzoyl-2-aza-bicyclo[2.2.2]octane 

Relevant articles and documents

Piperadinyl-substituted pyridylalkane, alkene and alkine carboxamides

The invention relates to new piperidinyl-substituted pyridyl carboxamides of the general formula (I), wherein the structure element E has meanings (E1) or (E2) and whereby the heterocyclic ring can optionally have a double bond. These substances have especially high cytostatic activities and pronounced immunosuppressive properties which make them suitable for therapeutic treatment in broad tumor spectrum.

Benzodiazepine derivatives

Compounds of Formula (I), and salts and prodrugs thereof, wherein R1 represents H, optionally substituted C1-6 alkyl or C3-7 cycloalkyl; R2 is NHR12 or (CH2)s R13 where 5 is 0, 1 or 2; R3 represents C1-6 alkyl, halo or NR6 R7 ; R4 and R5 are H, C1-12 alkyl optionally substituted by NR9 R9' or an azacyclic or azabicyclic group, optionally substituted C4-9 cycloalkyl, C4-9 cycloalkyl C1-4 alkyl, aryl, arylC1-6 alkyl or azacyclic or azabicyclic groups, or R4 and R5 together form the residue of an optionally substituted azacyclic or azabicyclic ring system; x is 0, 1, 2 or 3; R12 is optionally substituted phenyl or pyridyl; R13 represents a group (A) wherein R14 is H or C1-6 alkyl; R15 is H, C1-6 alkyl, halo or NR6 R7 ; and the dotted line is an optional covalent bond; are CCK and/or gastrin antagonists useful in therapy. STR1

Synthesis of analogues of N (2 chloroethyl) N' trans 4 methylcyclohexyl) N nitrosourea for evaluation as anticancer agents

The superior activity of N (2 chloroethyl) N' (trans 4 methylcyclohexyl) N nitrosourea (MeCCNU) against advanced murine Lewis lung carcinoma in comparisons with the cis form and other nitrosoureas prompted the synthesis of a number of MeCCNU analogues, including several cis trans pairs. The methyl group was replaced by a variety of substituents (CO2H, CH2CO2H, CO2Me, CH2OAc, CH2Cl, OMe); the trans 3 methylcyclohexyl, cis 2 methyl 1,3 dithian 5 yl, cis and trans 2 methyl 1,3 dithian 5 yl tetraoxide, and 1 methylhexyl (open chain) analogues were also prepared. Preliminary tests against murine leukemia L1210 revealed therapeutic indices (ED50/LD10) ranging from 0.26 to 0.79; all but 3 analogues effected 50% cure rates at nontoxic doses, the open chain analogue being one of the least active. In terms of therapeutic index, diequatorial (trans 4) isomers were, with one exception, as active as or, in 4 of the 8 examples, somewhat more active than the corresponding axial equatorial (cis 4) isomers. In this series, 4 of the 5 2-fluoroethyl analogues prepared were clearly inferior to the corresponding 2 chloroethyl analogues.