278-08-0

Basic information

• Product Name: 3-Azabicyclo[3.2.0]heptane
• Synonyms: 3-Azabicyclo[3.2.0]heptane;3-AZABICYCLO[3.2.0]HEPTANE HCL
• CAS NO: 278-08-0
• Molecular Formula: C₆H₁₁N
• Molecular Weight: 97.15824
• Mol File: 278-08-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 135-137 °C
• Appearance: /
• Density: 0.959±0.06 g/cm3(Predicted)
• PKA: 11.44±0.20(Predicted)
• CAS DataBase Reference: 3-Azabicyclo[3.2.0]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Azabicyclo[3.2.0]heptane(278-08-0)
• EPA Substance Registry System: 3-Azabicyclo[3.2.0]heptane(278-08-0)

Safety Data

• Hazardous Substances Data: 278-08-0(Hazardous Substances Data)

Usage

General Description

3-Azabicyclo[3.2.0]heptane, also known as 3-Azabicyclo[3.2.0]heptane, is a bicyclic compound with a nitrogen atom embedded within the ring structure. It is widely used in the pharmaceutical and chemical industries as a building block for the synthesis of various organic molecules. Due to its rigid and compact structure, 3-Azabicyclo[3.2.0]heptane is commonly employed as a chiral auxiliary in asymmetric synthesis, allowing for the production of enantiomerically pure compounds. It is also utilized as a precursor in the preparation of heterocyclic compounds and is a valuable intermediate in the production of pharmaceuticals, agrochemicals, and natural products. Additionally, 3-Azabicyclo[3.2.0]heptane has potential applications in medicinal chemistry and drug discovery, making it a versatile and important chemical in the field of organic synthesis.

Upstream product

• 124-02-7 diallylamine 

Relevant articles and documents

Photocycloaddition of N-Benzylmaleimide to Alkenes As an Approach to Functional 3-Azabicyclo[3.2.0]heptanes

A one-step synthesis of functionalized 3-azabicyclo[3.2.0]heptanes by [2+2]-photochemical intermolecular cycloaddition of N-benzylmaleimide to alkenes was elaborated. The obtained compounds were easily transformed into the bi- and tricyclic analogues of piperidine, morpholine, piperazine, and GABA, which are advanced building blocks for drug discovery.

Iron-catalyzed [2π + 2π] cycloaddition of α,ω-dienes: The importance of redox-active supporting ligands

The bis(imino)pyridine iron bis(dinitrogen) complex, (iPrPDI)Fe(N2)2 (iPrPDI = 2,6-(2,6-iPr2C6H3NCR)2C5H3N), serves as an efficient precursor for the catalytic [2π + 2π] cycloaddition of α,ω-dienes to yield the corresponding bicycles. For amine substrates, the rate of catalytic turnover increases with the size of the nitrogen substituents, demonstrating competing heterocycle coordination and product inhibition. In one case, a bis(imino)pyridine iron azobicycloheptane product was characterized by X-ray diffraction. Preliminary mechanistic studies highlight the importance of the redox activity of the bis(imino)pyridine ligand to maintain the ferrous oxidation state throughout the catalytic cycle. Copyright