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

• ChemBase ID: 147681
• Molecular Formular: C6H7NO
• Molecular Mass: 109.12588
• Monoisotopic Mass: 109.05276385
• SMILES: C1[C@@H]2C=C[C@H]1NC2=O
• Canonical SMILES: C1[C@@H]2C=C[C@H]1NC2=O
• InChI: 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
• InChIKey: DDUFYKNOXPZZIW-CRCLSJGQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4R)-2-azabicyclo[2.2.1]hept-5-en-3-one
• IUPAC Traditional name: vince lactam
• Synonyms: (±)-2-Azabicyclo[2.2.1]hept-5-en-3-one; 4-Amino-2-cyclopentene-1-carboxylic acid lactam; 2-Azabicyclo[2.2.1]hept-5-en-3-one; (1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one; (±)-2-氮杂双环[2.2.1]庚-5-烯-3-酮; 文斯内酯; 2-氮杂双环[2.2.1]庚-5-烯-3-酮; (1S)-(+)-2-氮杂双环[2.2.1]庚-5-烯-3-酮

Database IDs

• CAS Number: 130931-83-8; 49805-30-3
• MDL Number: MFCD00211275; MFCD00213364
• Beilstein Number: 508342
• PubChem SID: 24860009; 162241868; 24867650
• PubChem CID: 11789150

CALCULATED PROPERTIES

• Acid pKa: 14.183221
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.21183439
• LogD (pH = 7.4): -0.21183443
• Log P: -0.21183437
• Molar Refractivity: 30.3346 cm^3
• Polarizability: 11.299311 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 54-58 °C(lit.); 94-97 °C(lit.)
• Boiling Point: 102-106 °C/0.25 mmHg(lit.)
• Flash Point: 110 °C; 230 °F
• Optical Rotation: [α]20/D +565°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1; 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98%; 98%
• Optical Purity: ee: 99% (HPLC)
• Empirical Formula (Hill Notation): C6H7NO

DETAILS

Sigma Aldrich - 441287

Packaging
1, 5 g in glass bottle
Application
This lactam and its antipode are precursors to the enantiomers of the carbocyclic nucleoside carbovir.

Sigma Aldrich - 331910

Packaging
1, 5 g in glass bottle