(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide

• ChemBase ID: 68402
• Molecular Formular: C14H26N2O
• Molecular Mass: 238.36904
• Monoisotopic Mass: 238.20451346
• SMILES: C1N[C@@H](C[C@@H]2CCCC[C@H]12)C(=O)NC(C)(C)C
• Canonical SMILES: O=C([C@H]1NC[C@@H]2[C@H](C1)CCCC2)NC(C)(C)C
• InChI: InChI=1S/C14H26N2O/c1-14(2,3)16-13(17)12-8-10-6-4-5-7-11(10)9-15-12/h10-12,15H,4-9H2,1-3H3,(H,16,17)/t10-,11+,12-/m0/s1
• InChIKey: UPZBXVBPICTBDP-TUAOUCFPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide
• IUPAC Traditional name: (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide
• Synonyms: (3S,4AS,8aS)-N-(tert-Butyl)decahydroisoquinoline-3-carboxamide; [3S-(3α,4aβ,8aβ)]-N-(tert-Butyl)decahydro-3-isoquinolinecarboxamide; (3S,4aS,8aS)-N-(1,1-Dimethylethyl)decahydro-3-isoquinolinecarboxamide; (S,S,S)-N-tert-Butyldecahydroisoquinoline-3-carboxamide; (3S,4aS,8aS)-Decahydro-N-t-butyl-3-isoquinolinecarboxamide; N-(tert-butyl)decahydroisoquinoline-3-carboxamide; [3S-(3α,4aβ,8aβ)]-N-(叔丁基)十氢-3-异喹啉甲酰胺

Database IDs

• CAS Number: 168899-60-3; 136465-81-1
• MDL Number: MFCD01313226
• PubChem SID: 162034133; 24870541
• PubChem CID: 454736

CALCULATED PROPERTIES

• Acid pKa: 15.833718
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.1776088
• LogD (pH = 7.4): 0.23290724
• Log P: 1.8955237
• Molar Refractivity: 69.6098 cm^3
• Polarizability: 27.793371 Å^3
• Polar Surface Area: 41.13 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Off-White Solid
• Melting Point: 109-111°C; 112-115 °C(lit.)
• Optical Rotation: [α]22/D -71°, c = 1 in methanol

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false

Product Information

• Purity: 95%; 95+%; 98%
• Empirical Formula (Hill Notation): C14H26N2O

DETAILS

Sigma Aldrich - 468916

Packaging
1, 5 g in glass bottle
Application
Fragment present in various HIV-1 protease inhibitors currently in clinical trials for AIDS treatment.1,2

Toronto Research Chemicals - D211100

Intermediate in the production of HIV protease inhibitors

REFERENCES

• Zhou, L, et al.: Chem. Pharm. Bull., 56, 1147 (2008)
• Cunico, W., et al.: Lett. Drug Des. Discov., 5, 178 (2008)
• Righi, G., et al.: Bioorg. Med. Chem., 16, 902 (2008)