1-[(1S,2R,6S,14R,15R,16S)-11,15-dimethoxy-3-methyl-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl]ethan-1-one

• ChemBase ID: 167733
• Molecular Formular: C23H29NO4
• Molecular Mass: 383.48066
• Monoisotopic Mass: 383.20965841
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]45[C@@]3([C@H]([C@]([C@H](C4)C(=O)C)(CC5)OC)O2)CCN1C)OC
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@]24CC[C@@]1(OC)[C@H](C2)C(=O)C)C
• InChI: InChI=1S/C23H29NO4/c1-13(25)15-12-21-7-8-23(15,27-4)20-22(21)9-10-24(2)17(21)11-14-5-6-16(26-3)19(28-20)18(14)22/h5-6,15,17,20H,7-12H2,1-4H3/t15-,17-,20-,21-,22+,23-/m1/s1
• InChIKey: KRWAWNXEYPCCLG-LLGZQOTFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2R,6S,14R,15R,16S)-11,15-dimethoxy-3-methyl-13-oxa-3-azahexacyclo[13.2.2.1^2,^8.0^1,^6.0^6,^1^4.0^7,^1^2]icosa-7,9,11-trien-16-yl]ethan-1-one
• IUPAC Traditional name: 1-[(1S,2R,6S,14R,15R,16S)-11,15-dimethoxy-3-methyl-13-oxa-3-azahexacyclo[13.2.2.1^2,^8.0^1,^6.0^6,^1^4.0^7,^1^2]icosa-7,9,11-trien-16-yl]ethanone
• Synonyms: Hydrothevinone; 7α-Acetyl-6,14-endo-ethanotetrahydrothebaine; 1-[(5α,7α)-4,5-Epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl]ethanone; Dihydrothevinone

Database IDs

• CAS Number: 16196-82-0
• PubChem SID: 162261866
• PubChem CID: 85327

CALCULATED PROPERTIES

• Acid pKa: 17.060514
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.7228336
• LogD (pH = 7.4): 1.0238757
• Log P: 2.1731749
• Molar Refractivity: 105.1874 cm^3
• Polarizability: 41.48228 Å^3
• Polar Surface Area: 48.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D449840

Intermediate in the preparation of Buprenorphine derivatives and analgesic compounds.

REFERENCES

• Marton, J., et al.: Bioorg. Med. Chem., 5, 369 (1997)