1122-09-4

Basic information

• Product Name: 3-Azabicyclo[3.2.0]heptane-2,4-dione
• Synonyms: 3-Azabicyclo[3.2.0]heptane-2,4-dione
• CAS NO: 1122-09-4
• Molecular Formula: C₆H₇NO₂
• Molecular Weight: 125.126
• Mol File: 1122-09-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 134-135°
• Boiling Point: 318°C at 760 mmHg
• Flash Point: 167.6°C
• Appearance: /
• Density: 1.327g/cm³
• Vapor Pressure: 0.000371mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: 3-Azabicyclo[3.2.0]heptane-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Azabicyclo[3.2.0]heptane-2,4-dione(1122-09-4)
• EPA Substance Registry System: 3-Azabicyclo[3.2.0]heptane-2,4-dione(1122-09-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1122-09-4(Hazardous Substances Data)

Usage

General Description

3-Azabicyclo[3.2.0]heptane-2,4-dione, also known as piperidinedione, is a chemical compound with a bicyclic structure containing nitrogen. It is a cyclic diketone and is commonly used as a building block in organic synthesis. The compound has potential applications in the pharmaceutical industry for the synthesis of various drugs and pharmaceutical intermediates. It is also used in the preparation of heterocyclic compounds and can act as a precursor for the synthesis of other nitrogen-containing compounds. Additionally, piperidinedione has been studied for its potential biological activity and is of interest in the development of new therapeutic agents.

InChI:InChI=1/C6H7NO2/c8-5-3-1-2-4(3)6(9)7-5/h3-4H,1-2H2,(H,7,8,9)

Upstream product

• 4462-96-8 cis-1,2-cyclobutane dicarboxylic anhydride 
• 541-59-3 maleiimide 
• 74-85-1 ethene 

Downstream Products

• 192824-73-0 (1S,4S,5R)-3-Benzyl-4-hydroxy-3-aza-bicyclo[3.2.0]heptan-2-one 

Relevant articles and documents

Finding the Perfect Match: A Combined Computational and Experimental Study toward Efficient and Scalable Photosensitized [2 + 2] Cycloadditions in Flow

With ever-evolving light-emitting diode (LED) technology, classical photochemical transformations are becoming accessible with more efficient and industrially viable light sources. In combination with a triplet sensitizer, we report the detailed exploration of [2 + 2] cycloadditions, in flow, of various maleic anhydride derivatives with gaseous ethylene. By the use of a flow reactor capable of gas handling and LED wavelength/power screening, an in-depth optimization of these reactions was carried out. In particular, we highlight the importance of matching the substrate and sensitizer triplet energies alongside the light source emission wavelength and power. Initial triplet-sensitized reactions of maleic anhydride were hampered by benzophenone's poor absorbance at 375 nm. However, density functional theory (DFT) calculations predicted that derivatives such as citraconic anhydride have low enough triplet energies to undergo triplet transfer from thioxanthone, whose absorbance matches the LED emission at 375 nm. This observation held true experimentally, allowing optimization and further exemplification in a larger-scale reactor, whereby >100 g of material was processed in 10 h. These straightforward DFT calculations were also applied to a number of other substrates and showed a good correlation with experimental data, implying that their use can be a powerful strategy in targeted reaction optimization for future substrates.

The synthesis of unsubstituted cyclic imides using hydroxylamine under microwave irradiation

Unsubstituted cyclic imides were synthesized from a series of cyclic anhydrides, hydroxylamine hydrochloride (NH2OH·HCl), and 4-N,N-dimethylamino-pyridine (DMAP, base catalyst) under microwave irradiation in monomode and multimode microwaves. This novel microwave synthesis produced high yields of the unsubstituted cyclic imides for both the monomode (61-81%) and multimode (84-97%) microwaves.

OLEFIN CYCLISATIONS OF HINDERED α-ACYLIMINIUM IONS

Stereocontrolled NaBH4/H+-reduction of 3,4-cis-disubstituted N-alkenyl imides 1-5 leads to secondary hydroxylactams.Tertiary hydroxylactams are formed via addition of MeMgCl to imides 2 and 4.HCOOH-Cyclisation of the hydroxylactams affords polycyclic piperidines through stereoselective α-acyliminium ring closure.Concomitant synchronous and stepwise cyclisation pathways are operative in the anti-periplanar addition of tertiary α-acyliminium ions to Me substituted olefins 8c and 11c.