(3aS,4R,5S,6aR)-4-(hydroxymethyl)-2-oxo-hexahydro-2H-cyclopenta[b]furan-5-yl 4-phenylbenzoate

• ChemBase ID: 136898
• Molecular Formular: C21H20O5
• Molecular Mass: 352.3805
• Monoisotopic Mass: 352.13107374
• SMILES: c1ccc(cc1)c1ccc(cc1)C(=O)O[C@H]1C[C@@H]2[C@H]([C@@H]1CO)CC(=O)O2
• Canonical SMILES: OC[C@@H]1[C@H](C[C@@H]2[C@H]1CC(=O)O2)OC(=O)c1ccc(cc1)c1ccccc1
• InChI: InChI=1S/C21H20O5/c22-12-17-16-10-20(23)25-18(16)11-19(17)26-21(24)15-8-6-14(7-9-15)13-4-2-1-3-5-13/h1-9,16-19,22H,10-12H2/t16-,17-,18+,19-/m0/s1
• InChIKey: SZJVIFMPKWMGSX-OKYOBFRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,4R,5S,6aR)-4-(hydroxymethyl)-2-oxo-hexahydro-2H-cyclopenta[b]furan-5-yl 4-phenylbenzoate
• IUPAC Traditional name: (3aS,4R,5S,6aR)-4-(hydroxymethyl)-2-oxo-hexahydrocyclopenta[b]furan-5-yl 4-phenylbenzoate
• Synonyms: (+)-Corey lactone, 4-phenylbenzoate alcohol; (+)-科里内酯4-苯基苯甲酸醇

Database IDs

• CAS Number: 39265-57-1
• MDL Number: MFCD00274286
• PubChem SID: 162231165; 24868773
• PubChem CID: 289982

CALCULATED PROPERTIES

• Acid pKa: 15.374329
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.6427593
• LogD (pH = 7.4): 2.6427593
• Log P: 2.6427593
• Molar Refractivity: 94.8059 cm^3
• Polarizability: 38.50716 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 134-136 °C(lit.)
• Optical Rotation: [α]20/D +87°, c = 1 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 99%
• Empirical Formula (Hill Notation): C21H20O5

DETAILS

Sigma Aldrich - 453226

Packaging
1 g in glass bottle
Application
Key intermediate in the synthesis of prostaglandins.1,2