benzyl (5Z)-7-[(1R,2R,3R)-5-(acetyloxy)-2-formyl-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate

• ChemBase ID: 159397
• Molecular Formular: C27H36O7
• Molecular Mass: 472.57054
• Monoisotopic Mass: 472.24610349
• SMILES: [C@H]1([C@H](C(C[C@H]1OC1OCCCC1)OC(=O)C)C/C=C\CCCC(=O)OCc1ccccc1)C=O
• Canonical SMILES: O=C[C@H]1[C@H](OC2CCCCO2)CC([C@@H]1C/C=C\CCCC(=O)OCc1ccccc1)OC(=O)C
• InChI: InChI=1S/C27H36O7/c1-20(29)33-24-17-25(34-27-15-9-10-16-31-27)23(18-28)22(24)13-7-2-3-8-14-26(30)32-19-21-11-5-4-6-12-21/h2,4-7,11-12,18,22-25,27H,3,8-10,13-17,19H2,1H3/b7-2-/t22-,23-,24?,25-,27?/m1/s1
• InChIKey: VHAWRDIGRHDHSJ-KNKWHNQXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (5Z)-7-[(1R,2R,3R)-5-(acetyloxy)-2-formyl-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate
• IUPAC Traditional name: benzyl (5Z)-7-[(1R,2R,3R)-5-(acetyloxy)-2-formyl-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate
• Synonyms: 7-[5-(Benzoyloxy)-2-formyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopentyl]-5-heptenoic Acid Benzyl Ester; (5Z)-7-[(5-Acetyloxy-2-formyl-3-tetrahydropyranyloxy)cyclopentyl]-5-heptenoic Acid Benzyl Ester

Database IDs

• PubChem SID: 162253532
• PubChem CID: 71312966

CALCULATED PROPERTIES

• Acid pKa: 12.275395
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.8020556
• LogD (pH = 7.4): 3.8020499
• Log P: 3.8020556
• Molar Refractivity: 127.6384 cm^3
• Polarizability: 50.307724 Å^3
• Polar Surface Area: 88.13 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Yellow Oil

DETAILS

Toronto Research Chemicals - A187335

Intermediate in the preparation of Lubiprostone.