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

• ChemBase ID: 167734
• Molecular Formular: C24H29NO6
• Molecular Mass: 427.49016
• Monoisotopic Mass: 427.19948765
• 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(=O)OC)OC
• Canonical SMILES: COC(=O)N1CC[C@]23[C@]45[C@H]1Cc1c2c(O[C@H]3[C@@](CC4)([C@H](C5)C(=O)C)OC)c(cc1)OC
• InChI: InChI=1S/C24H29NO6/c1-13(26)15-12-22-7-8-24(15,30-4)20-23(22)9-10-25(21(27)29-3)17(22)11-14-5-6-16(28-2)19(31-20)18(14)23/h5-6,15,17,20H,7-12H2,1-4H3/t15-,17-,20-,22-,23+,24-/m1/s1
• InChIKey: IVVZNNMLCBSTLU-TZJJEGCPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,2R,6S,14R,15R,16S)-16-acetyl-11,15-dimethoxy-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-triene-3-carboxylate
• IUPAC Traditional name: methyl (1S,2R,6S,14R,15R,16S)-16-acetyl-11,15-dimethoxy-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-triene-3-carboxylate
• Synonyms: Hydrothevinone N-Methyl Ester; Dihydrothevinone N-Methyl Ester

Database IDs

• PubChem SID: 162261867
• PubChem CID: 71316206

CALCULATED PROPERTIES

• Acid pKa: 17.49462
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.0193603
• LogD (pH = 7.4): 2.0193603
• Log P: 2.0193603
• Molar Refractivity: 111.0822 cm^3
• Polarizability: 43.902214 Å^3
• Polar Surface Area: 74.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D449850

Intermediate in the preparation of Buprenorphine derivatives and analgesic compounds.

REFERENCES

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