| Identification | More | [Name]
D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid | [CAS]
103733-65-9 | [Synonyms]
1,2,3,4-D-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID
1,2,3,4-TETRAHYDROISOQUINOLINE-(3R)-CARBOXYLIC ACID
3-ISOQUINOLINECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-, (3R)-
(3R)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID
D-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID
D-[3R]-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID
D-TIC
H-D-TIC-OH
(R)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID
(R)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID
RARECHEM BK PT 0079
D-1,2,3,4-Tetrahydroisoquinoline
(R)-1,2,3,4-Tetrahydro-3-Isoquinoliceearboxylic Acid
(3R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid | [EINECS(EC#)]
266-580-4 | [Molecular Formula]
C10H11NO2 | [MDL Number]
MFCD00144038 | [Molecular Weight]
177.2 | [MOL File]
103733-65-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
320-323 °C (decomp) | [Boiling point ]
372.0±42.0 °C(Predicted) | [density ]
1.225±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Aqueous Acid (Slightly), Aqueous Base (Sparingly, Sonicated) | [form ]
Crystalline Powder | [pka]
2.21±0.20(Predicted) | [color ]
White | [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 | [SMILES]
C1C2=C(C=CC=C2)C[C@H](C(O)=O)N1 | [CAS DataBase Reference]
103733-65-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29334900 |
| Hazard Information | Back Directory | [Description]
D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid ((3R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid) is a magnetic, neutral compound. It is used as a pharmacological study to investigate the reaction mechanism and kinetics of the deuteration process. The asymmetric synthesis of D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid has been investigated using vinylene chloride and hydantoin as reactants. There are various parameters that affect the kinetics of this reaction such as solvent type and temperature. The nitric oxide synthase inhibitor activity of D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid has been studied in vitro. Results have shown that it inhibits nitric oxide synthase by binding to the heme iron of the enzyme and preventing the conversion of arginine | [Chemical Properties]
White solid | [Uses]
(R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance. | [Definition]
ChEBI: D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is a member of isoquinolines. | [Synthesis]
General procedure for the synthesis of (R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid from formaldehyde and D-phenylalanine:
1. Preparation of (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid: D-phenylalanine (50 g, 0.3 mol), concentrated hydrochloric acid (386 mL), and 37% wt formalin (113.7 mL) were mixed, and the reaction was carried out for 4 h at 95 °C with vigorous stirring. Upon completion of the reaction, the mixture was cooled to room temperature and stirring was continued for 2 hours. The reaction mixture was filtered and the precipitate was washed with cold water to afford (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (25 g, 42% yield) in white solid form.
2. Esterification reaction: benzyl alcohol (64 g) and p-toluenesulfonic acid (26.9 g) were added to the above product, and the reaction was carried out under reflux in a Dean-Stark apparatus with benzene (400 mL) as solvent. After completion of the reaction, the solvent was removed in vacuum and the crude product was ground with ether to obtain a solid, which was subsequently recrystallized with water and methanol to give (R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (28 g, 35% yield) in white solid form. | [References]
[1] MedChemComm, 2014, vol. 5, # 9, p. 1381 - 1383
[2] Journal of Medicinal Chemistry, 1988, vol. 31, # 11, p. 2092 - 2097
[3] Patent: WO2004/72086, 2004, A2. Location in patent: Page 182
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5727 - 5737 |
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