methyl (1S,4R)-4-acetamidocyclopent-2-ene-1-carboxylate

• ChemBase ID: 159124
• Molecular Formular: C9H13NO3
• Molecular Mass: 183.20442
• Monoisotopic Mass: 183.08954328
• SMILES: C1=C[C@H](C[C@H]1NC(=O)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1C=C[C@@H](C1)NC(=O)C
• InChI: InChI=1S/C9H13NO3/c1-6(11)10-8-4-3-7(5-8)9(12)13-2/h3-4,7-8H,5H2,1-2H3,(H,10,11)/t7-,8+/m1/s1
• InChIKey: NEJBWENICROWTO-SFYZADRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,4R)-4-acetamidocyclopent-2-ene-1-carboxylate
• IUPAC Traditional name: methyl (1S,4R)-4-acetamidocyclopent-2-ene-1-carboxylate
• Synonyms: cis-(+/-)-4-(Acetylamino)-2-Cyclopentene-1-carboxylic Acid Methyl Ester; (1R,4S)-rel-4-(Acetylamino)-2-cyclopentene-1-carboxylic Acid Methyl Ester

Database IDs

• CAS Number: 61865-49-4
• PubChem SID: 162253259
• PubChem CID: 361509

CALCULATED PROPERTIES

• Acid pKa: 15.441163
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.2892867
• LogD (pH = 7.4): -0.28928605
• Log P: -0.28928602
• Molar Refractivity: 47.7474 cm^3
• Polarizability: 18.354876 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A168245

Carbovir intermediate.

REFERENCES

• Ikbal, M., et al.: Eur. J. Med. Chem., 24, 415 (1989)
• Mahmoudian, M., et al.: Enz. Microb. Technol., 14, 911 (1989)