(4S)-4-ethyl-4-hydroxy-1H,3H,4H,6H,7H,8H,10H-pyrano[3,4-f]indolizine-3,6,10-trione

• ChemBase ID: 168531
• Molecular Formular: C13H13NO5
• Molecular Mass: 263.24602
• Monoisotopic Mass: 263.07937252
• SMILES: c12c(COC(=O)[C@]1(O)CC)c(=O)n1c(c2)C(=O)CC1
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1C(=O)CCn1c2=O
• InChI: InChI=1S/C13H13NO5/c1-2-13(18)8-5-9-10(15)3-4-14(9)11(16)7(8)6-19-12(13)17/h5,18H,2-4,6H2,1H3/t13-/m0/s1
• InChIKey: IGKWOGMVAOYVSJ-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-ethyl-4-hydroxy-1H,3H,4H,6H,7H,8H,10H-pyrano[3,4-f]indolizine-3,6,10-trione
• IUPAC Traditional name: (4S)-4-ethyl-4-hydroxy-1H,7H,8H-pyrano[3,4-f]indolizine-3,6,10-trione
• Synonyms: (S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione; (4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione; (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

Database IDs

• CAS Number: 110351-94-5
• MDL Number: MFCD17011873
• PubChem SID: 162262663
• PubChem CID: 10220900

CALCULATED PROPERTIES

• Acid pKa: 11.708805
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.47680008
• LogD (pH = 7.4): -0.47682112
• Log P: -0.47679982
• Molar Refractivity: 65.7022 cm^3
• Polarizability: 24.798914 Å^3
• Polar Surface Area: 83.91 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - E917350

(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione is a key intermediate in the synthesis of Irinotecan (I767500) and Camptothecin (C175150) analogs.

REFERENCES

• Hsiang, Y., et al.: J. Biol. Chem., 260, 14873 (1985)
• Bao, Y., et al.: Chin. J. Med. Chem., 18, 263 (1985)
• Miao, Z., et al.: Bioorg. Med. Chem., 16, 1493 (1985)