2-Azabicyclo[2.2.1]hept-5-en-3-one

Base Information

• Chemical Name: 2-Azabicyclo[2.2.1]hept-5-en-3-one
• CAS No.: 49805-30-3
• Molecular Formula: C6H7NO
• Molecular Weight: 109.128
• Hs Code.: 29337900
• European Community (EC) Number: 421-830-3,610-480-9
• DSSTox Substance ID: DTXSID40868505
• Nikkaji Number: J277.618I
• Mol file: 49805-30-3.mol

Synonyms:2-ABHEO;2-azabicyclo(2.2.1)hept-5-en-3-one;6-azabicyclo(3.2.0)hept-3-en-7-one

Chemical Property of 2-Azabicyclo[2.2.1]hept-5-en-3-one

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 0.3-1.06Pa at 25-40℃
• Melting Point: 54-58 °C(lit.)
• Refractive Index: 1.5040 (estimate)
• Boiling Point: 319.3 °C at 760 mmHg
• PKA: 15.48±0.20(Predicted)
• Flash Point: 167.1 °C
• PSA: 29.10000
• Density: 1.198 g/cm³
• LogP: 0.38970
• Storage Temp.: Refrigerator
• Solubility.: soluble in Methanol
• Water Solubility.: >1000 g/L (23 ºC)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 109.052763847
• Heavy Atom Count: 8
• Complexity: 162

Purity/Quality:

99% ^*data from raw suppliers

rac2-Azabicyclo[2.2.1]hept-5-en-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-43-22
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC1NC2=O
• Uses: Intermediate for pharmaceuticals. Product Data Sheet 2-Azabicyclo[2.2.1]hept-5-en-3-one was used in:preparation of (3aS,4R,6R,6aR)-6-((methoxy-methoxy)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine, a precursor of analog of bredininsynthesis of therapeutic drugschemoenzymatic synthesis of (?)-carbovir Abacavir intermediate. 2-Azabicyclo[2.2.1]hept-5-en-3-one is used as an intermediate in the synthesis of carbocyclic sugar amines, carbanucleosides, and carbocyclic dinucleotide analogues.

Technology Process of 2-Azabicyclo[2.2.1]hept-5-en-3-one

There total 13 articles about 2-Azabicyclo[2.2.1]hept-5-en-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + cyanogen chloride (506-77-4) → 2-azabicyclo[2.2.1.]hept-5-en-3-one (49805-30-3)

Guidance literature:

With sodium hydroxide; In methanol; at 0 - 5 ℃; for 8h; pH=4 - 5;

Reference yield: 94.3%

→ 2-azabicyclo[2.2.1.]hept-5-en-3-one (49805-30-3)

Guidance literature:

Reference yield: 79.3%

P-toluenesulfonyl cyanide (19158-51-1) → 2-azabicyclo[2.2.1.]hept-5-en-3-one (49805-30-3)

Guidance literature:

upstream raw materials:

isocyanate de chlorosulfonyle

cyclopenta-1,3-diene

P-toluenesulfonyl cyanide

3-tosyl-2-azabicyclo [2.2.1]hepta-2,5-diene

Downstream raw materials:

cis-4-amino-2-cyclopentenecarboxylic acid methyl ester hydrochloride

(1R,2R,4S,5S)-2-Benzyl-5-hydroxy-2-aza-bicyclo[2.2.1]heptan-3-one

(1R,2R,4S)-2-Benzyl-2-aza-bicyclo[2.2.1]heptane-3,5-dione

N-((1R,3S)-3-Hydroxymethyl-cyclopentyl)-4-methyl-benzenesulfonamide

Refernces

Synthesis and antiviral activity of carbocyclic analogues of xylofuranosides of 2-amino-6-substituted-purines and 2-amino-6-substituted-8-azapurines

10.1021/jm00394a017

The research focused on the synthesis and antiviral activity of carbocyclic analogues of xylofuranosides of 2-amino-6-substituted-purines and 2-amino-6-substituted-8-azapurines. The purpose of this study was to explore the potential of these carbocyclic nucleoside analogues as antiviral agents, particularly against herpes simplex virus (HSV-1 and HSV-2), human cytomegalovirus (CMV), and varicella-zoster virus (VZV). The researchers synthesized a series of compounds, including carbocyclic xylofuranosylguanine (C-xylo-G, compound 9) and its 8-aza analogue (compound 13), through a series of chemical reactions involving precursors such as 2-amino-4,6-dichloropyrimidine and 2-azabicyclo[2.2.1]hept-5-en-3-one. The conclusions drawn from the study were that compounds 9 and 13 exhibited significant antiviral activity, with compound 9 being more potent against both HSV-1 and HSV-2. Additionally, compound 9 demonstrated potent activity against CMV and VZV, making it a promising candidate for further in vivo studies. The chemicals used in the synthesis process included various reagents and solvents such as triethyl orthoformate, acetic acid, zinc dust, p-chlorobenzenediazonium chloride, and dimethylformamide, among others.