(1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one, CAS No. 79200-56-9

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79200-56-9

Catalog No. EBD1616644

CAS 79200-56-9

Name (1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one

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Basic Information

Synonyms: (1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one 2-Azabicyclo[2.2.1]hept-5-en-3-one,(1R,4S)- (1R)-(-)-2-Azabicyclo[2.2.1]hept-5-en-3-one (-)-vincelactam (-)-2-Azabicyclo[2.2.1]hept-5-en-3-one

Molecular Formula: C6H7NO

Molecular Weight: 109.13

MDL Number: MFCD00211274

Categories: Synthetic Chemistry > Organic Building Blocks > Carboxylic Acids and Esters

Product Description:

(1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one, commonly known as (-)-Vince lactam, is a chiral bicyclic lactam with a rigid azabicyclo[2.2.1]heptene framework. It features a bridgehead nitrogen and an unsaturated double bond, providing a versatile scaffold for stereoselective synthesis. This compound is a key chiral building block in the pharmaceutical industry, particularly for the production of carbocyclic nucleoside analogues such as abacavir, an antiretroviral drug used in HIV therapy. Its enantiomerically pure form enables the construction of complex molecules with defined stereochemistry, making it indispensable in medicinal chemistry for developing antiviral and anticancer agents. Additionally, it serves as a precursor for other bioactive compounds and is valued for its stability and reactivity in synthetic transformations.

Physical Properties

Melting Point: 94-97 °C(lit.)

Boiling Point: 319.302 °C at 760 mmHg

Flash Point: 167.131 °C

Density: 1.198 g/cm3

Analytical Data

Appearance: Off-white to beige crystals or crystalline powder