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

Description

3-Azabicyclo[3.2.0]heptane is a bicyclic compound featuring a nitrogen atom within its ring structure, known for its rigid and compact nature. It serves as a crucial building block in the synthesis of a variety of organic molecules across the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
3-Azabicyclo[3.2.0]heptane is used as a chiral auxiliary in asymmetric synthesis for the production of enantiomerically pure compounds, which is vital for creating effective and safe medications with minimized side effects.
Used in Chemical Industry:
As a precursor, 3-Azabicyclo[3.2.0]heptane is instrumental in the preparation of heterocyclic compounds, which are essential components in various chemical products.
Used in Medicinal Chemistry and Drug Discovery:
3-Azabicyclo[3.2.0]heptane is utilized as a valuable intermediate in the development and production of pharmaceuticals, agrochemicals, and natural products, contributing to the advancement of new and improved treatments.
Overall, 3-Azabicyclo[3.2.0]heptane's applications span across multiple industries, highlighting its versatility and significance in organic synthesis and the development of new chemical entities.

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