2-Azabicyclo[2.2.1]hept-5-en-3-one - CAS 49805-30-3

Name: 2-Azabicyclo[2.2.1]hept-5-en-3-one
Brand: BOC Sciences
Rating: 5 (1 reviews)

Technical Data

IUPAC Name:	2-azabicyclo[2.2.1]hept-5-en-3-one
Description:	2-Azabicyclo[2.2.1]hept-5-en-3-one (CAS# 49805-30-3) is a useful reagent in the synthesis of carbocyclic sugar amines, carbanucleosides, and carbocyclic dinucleotide analogues (1). rac 2-Azabicyclo[2.2.1]hept-5-en-3-one is also an intermediate of Abacavir (A104990), a carbocyclic 2'-deoxyguanosine nucleoside reverse transcriptase inhibitor and anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.
Molecular Weight:	109.13
Molecular Formula:	C6H7NO
Canonical SMILES:	C1C2C=CC1NC2=O
InChI:	InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)
InChI Key:	DDUFYKNOXPZZIW-UHFFFAOYSA-N
Boiling Point:	102-106 °C (0.2 mmHg)
Purity:	97.0 %
Density:	1.198 g/cm³
MDL:	MFCD00213364
LogP:	0.38970

GHS Hazard Statement:	H302: Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement:	P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, and P501
Signal Word:	Warning

Publication Number	Title	Priority Date
CN-111484418-A	Preparation method of 4-amino-2-cyclopentene-1-methanol hydrochloride	20200430
WO-2021201089-A1	Hollow microballoons	20200331
CN-111072547-A	Chemical preparation method of 2-azabicyclo [2.2.1] hept-5-ene-3-ketone with optical activity	20191127
US-2020317606-A1	2-difluoro substituted 4-aminocyclopentanecarboxylic acids as inhibitors of gamma-aminobutyric acid aminotransferase and human ornithine aminotransferase	20190403
US-2020270232-A1	Inhibitors of integrated stress response pathway	20190225

PMID	Publication Date	Title	Journal
22681478	20120808	2-Azabicyclo[2.2.1]hept-5-en-3-one: chemical profile of a versatile synthetic building block and its impact on the development of therapeutics	Chemical reviews
22359066	20120507	Promiscuous enantioselective (-)-γ-lactamase activity in the Pseudomonas fluorescens esterase I	Organic & biomolecular chemistry
16996741	20061215	Synthesis of neplanocin F analogues as potential antiviral agents	Bioorganic & medicinal chemistry
16995703	20060929	Carbocyclic ribosylamines: synthesis of 5-substituted carbocyclic beta-ribofuranosylamines	The Journal of organic chemistry
18428951	20060701	Synthesis of carbovir and abacavir from a carbocyclic precursor	Current protocols in nucleic acid chemistry

Complexity:	162
Compound Is Canonicalized:	Yes
Covalently-Bonded Unit Count:	1
Defined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Exact Mass:	109.052763847
Formal Charge:	0
Heavy Atom Count:	8
Hydrogen Bond Acceptor Count:	1
Hydrogen Bond Donor Count:	1
Isotope Atom Count:	0
Monoisotopic Mass:	109.052763847
Rotatable Bond Count:	0
Topological Polar Surface Area:	29.1 Å²
Undefined Atom Stereocenter Count:	2
Undefined Bond Stereocenter Count:	0
XLogP3:	0.1