Vince lactam

Vince lactam^[1] is the commercial name given to the bicyclic molecule γ-lactam 2-azabicyclo[2.2.1]hept-5-en-3-one. This lactam is a versatile chemical intermediate used in organic and medicinal chemistry. It is used as a synthetic precursor for three drugs (approved or in clinical trials).^[2][3] It is named after Robert Vince who has used the structural features of this molecule for the preparation of carbocyclic nucleosides.^[4] Vince's work with this lactam eventually led to his synthesis of abacavir.^[5][6][7] Peramivir synthesis is also dependent on Vince lactam starting material.

Vince lactam

Names
Preferred IUPAC name 2-Azabicyclo[2.2.1]hept-5-en-3-one
Identifiers
CAS Number	(1S,4R): 130931-83-8 N (1R,4S): 79200-56-9 N
3D model (JSmol)	(1S,4R): Interactive image (1R,4S): Interactive image
ChemSpider	(1S,4R): 2007146 Y (1R,4S): 9963824 Y
EC Number	(1S,4R): 627-840-6 (1R,4S): 418-530-1
PubChem CID	(1S,4R): 11789150 (1R,4S): 2725037
CompTox Dashboard (EPA)	DTXSID401336090 (1R,4S): DTXSID10369337
InChI (1S,4R): InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m0/s1 Y Key: DDUFYKNOXPZZIW-CRCLSJGQSA-N Y (1R,4S): InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m1/s1 Key: DDUFYKNOXPZZIW-UHNVWZDZSA-N
SMILES (1S,4R): O=C1N[C@@H]2\C=C/[C@H]1C2 (1R,4S): C1[C@H]2C=C[C@@H]1NC2=O
Properties
Chemical formula	C6H7NO
Molar mass	109.128 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H317, H318
Precautionary statements	P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P333+P313, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Vince lactam has been extensively used for the preparation of various carbocyclic nucleosides with medicinal applications in mind, including carbocyclic puromycin (I),^[8] carbocyclic Ara-A (II),^[9] carbovir (III)^[10] and guanine as well as azaguanine carbocyclic derivatives (IV)^[11]

Vince lactam is also an intermediate in the synthesis of various nucleoside analogs such as difluoro guanosine derivatives (V),^[12][13] carbocyclic oxanosine and related derivatives (VI),^[14] and precursors for azidocarbonucleosides (VII).^[15] The lactam has found several applications in targeting an array of different diseased conditions by providing various non-nucleoside therapeutic molecules as well. Some well known examples include scaffolds for the preparation of glycosidase inhibitors (VIII)^[16] and GABA-AT inhibitors (IX).^[17]