(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

• ChemBase ID: 77362
• Molecular Formular: C10H11NO2
• Molecular Mass: 177.19984
• Monoisotopic Mass: 177.0789786
• SMILES: N1Cc2c(cccc2)C[C@@H]1C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1NCc2c(C1)cccc2
• InChI: InChI=1S/C10H11NO2/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9/h1-4,9,11H,5-6H2,(H,12,13)/t9-/m1/s1
• InChIKey: BWKMGYQJPOAASG-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• IUPAC Traditional name: (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• Synonyms: (R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid; (R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid; (R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid; H-D-Tic-OH; (R)-(+)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid; (-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid; L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid; L-3-Carboxy-1,2,3,4-tetrahydroisoquinoline; L-Porretine; (S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid; (R)-1,2,3,4-四氢-3-异喹啉羧酸; (R)-(+)-1,2,3,4-四氢异喹啉-3-羧酸

Database IDs

• CAS Number: 74163-81-8; 103733-65-9
• MDL Number: MFCD00144038
• Beilstein Number: 5378782
• PubChem SID: 162042235; 24888899
• PubChem CID: 712398

CALCULATED PROPERTIES

• Acid pKa: 1.8478861
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.2092154
• LogD (pH = 7.4): -1.213396
• Log P: -1.2092786
• Molar Refractivity: 48.4455 cm^3
• Polarizability: 18.996552 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Basic Water; Hot Water
• Apperance: Off-White Solid
• Melting Point: >225°C (dec.)
• Optical Rotation: [α]20/D +164±3°, c = 2% in 1 M NaOH; +163 (c=2 in 1N NaOH)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: 否
• 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: ≥98.0% (T); 95+%
• Impurities: ≤1% water
• Empirical Formula (Hill Notation): C10H11NO2
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 87433

Other Notes
Sterically constrained analogue of D-phenylalanine1; Auxiliary in enantioselective reduction2

Toronto Research Chemicals - T293755

Quinapril intermediate.

REFERENCES

• Cheng, S., et al.: Eur. J. Med. Chem., 44, 4904 (2009)
• Brust, A., et al.: J. Med. Chem., 52, 6991 (2009)
• Toussaint, M., et al.: Eur. Neuropsychopharmacol., 19, 504 (2009)