(1S,3R)-3-(methoxycarbonyl)cyclopentane-1-carboxylic acid

• ChemBase ID: 165235
• Molecular Formular: C8H12O4
• Molecular Mass: 172.17848
• Monoisotopic Mass: 172.07355886
• SMILES: C1C[C@H](C[C@H]1C(=O)O)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1CC[C@@H](C1)C(=O)O
• InChI: InChI=1S/C8H12O4/c1-12-8(11)6-3-2-5(4-6)7(9)10/h5-6H,2-4H2,1H3,(H,9,10)/t5-,6+/m0/s1
• InChIKey: FVUHGTQDOMGZOT-NTSWFWBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R)-3-(methoxycarbonyl)cyclopentane-1-carboxylic acid
• IUPAC Traditional name: (1S,3R)-3-(methoxycarbonyl)cyclopentane-1-carboxylic acid
• Synonyms: (1R-cis)-1,3-Cyclopentanedicarboxylic Acid Monomethyl Ester; (1S,3R)-3-(Methoxycarbonyl)cyclopentanecarboxylic Acid; (1R,3S)-1,3-Cyclopentanedicarboxylic Acid 1-Methyl Ester

Database IDs

• CAS Number: 96443-42-4
• PubChem SID: 162259368
• PubChem CID: 10888375

CALCULATED PROPERTIES

• Acid pKa: 4.2042723
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.50041634
• LogD (pH = 7.4): -2.2163184
• Log P: 0.8142264
• Molar Refractivity: 40.2539 cm^3
• Polarizability: 16.128157 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C988360

An intermediate in the stereoselective synthesis of Amidinomycin.

REFERENCES

• Chenevert, R., et al.: Chem. Lett., 93, 1 (1994)