(3S)-2-[(benzyloxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

• ChemBase ID: 70280
• Molecular Formular: C18H17NO4
• Molecular Mass: 311.33188
• Monoisotopic Mass: 311.11575803
• SMILES: C1N([C@@H](Cc2ccccc12)C(=O)O)C(=O)OCc1ccccc1
• Canonical SMILES: OC(=O)[C@@H]1Cc2ccccc2CN1C(=O)OCc1ccccc1
• InChI: InChI=1S/C18H17NO4/c20-17(21)16-10-14-8-4-5-9-15(14)11-19(16)18(22)23-12-13-6-2-1-3-7-13/h1-9,16H,10-12H2,(H,20,21)/t16-/m0/s1
• InChIKey: YWVQGUBCAUFBCP-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-2-[(benzyloxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• IUPAC Traditional name: (3S)-2-[(benzyloxy)carbonyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
• Synonyms: (S)-(+)-2-(Benzyloxycarbonyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid; (3S)-2-Carbobenzoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; (S)-(+)-2-(苄氧羰基)-1,2,3,4-四氢-3-异喹啉羧酸

Database IDs

• CAS Number: 79261-58-8
• MDL Number: MFCD00672545
• PubChem SID: 162036003; 24870241
• PubChem CID: 688307

CALCULATED PROPERTIES

• Acid pKa: 3.785936
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.4993492
• LogD (pH = 7.4): -0.053655453
• Log P: 3.2151294
• Molar Refractivity: 84.2476 cm^3
• Polarizability: 32.654037 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 137-141 °C(lit.)
• Optical Rotation: [α]24/D +22°, c = 1 in methanol

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95+%; 97%
• Empirical Formula (Hill Notation): C18H17NO4

DETAILS

Sigma Aldrich - 465054

Application
Building block for HIV protease inhibitors.1