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Chemical Structure| 74163-81-8 Chemical Structure| 74163-81-8
Chemical Structure| 74163-81-8

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(S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid contains a tetrahydroisoquinoline scaffold with potential effects on the nervous system.

Synonyms: L-Porretine; L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

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Product Details of (S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid

CAS No. :74163-81-8
Formula : C10H11NO2
M.W : 177.20
SMILES Code : [C@@H]2(NCC1=CC=CC=C1C2)C(=O)O
Synonyms :
L-Porretine; L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
MDL No. :MFCD00144533
InChI Key :BWKMGYQJPOAASG-VIFPVBQESA-N
Pubchem ID :2733226

Safety of (S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of (S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 74163-81-8 ]

[ 74163-81-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 74163-81-8 ]
  • [ 6624-49-3 ]
YieldReaction ConditionsOperation in experiment
83% With potassium permanganate; In N,N-dimethyl-formamide; at 0 - 20℃; for 100.5h;Inert atmosphere; At 0 C to a solution of 10.0 g (0.046 mmol) of (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in 200 ml of N,N-dimethylformamide 5.0 g (0.032 mmol) of KMnO4 was added, which took 30 min. The reaction mixture was stirred at room temperature for 100 h, and TLC (CCl3:CH3OH = 5:1) indicated the complete disappearance of (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid. The reaction mixture was evaporated under vacuum. The residue was washed with distilled water repeatedly to provide 8.1 g (83%) of the title compound as a yellow powder. ESI-MS (m/e) 174 [M + H]+; 1H NMR (300 MHz, DMSO) delta/ppm = 10.81 (s, 1 H), 9.52 (s, 1 H), 8.43 (s, 1 H), 7.52 (m, 4 H); 13C NMR (75 MHz, DMSO) delta/ppm = 164.9, 152.3, 143.5, 136.2, 131.3, 129.7, 127.2, 125.8.
  • 2
  • [ 67-56-1 ]
  • [ 74163-81-8 ]
  • [ 146074-43-3 ]
YieldReaction ConditionsOperation in experiment
71% With thionyl chloride; at 0 - 50℃;Inert atmosphere; Example 93(3R)-2-(2-(4-Chloro-3-(dibutylcarbamoyl)-5-methyl-lH-pyrazol-l-yl)-5-(naphthalen-2- ylsulfonylcarbamoyl)benzoyl)- 1 ,2,3 ,4-tetrahydroisoquinoline-3 -carboxylic acid(93) Intermediate 93 A: (R)-Methyl l,2,3,4-tetrahydroisoquinoline-3-carboxylatehydrochloride[00326] To (5)-l,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Aldrich, 500 mg, 2.82 mmol) in MeOH (2.8 mL) was added SOCl2 (824 μ,, 11.3 mmol) at 0 C. The resulting reaction mixture was allowed to warm to room temperature over 5 h and then stirred at 50 C overnight. The reaction mixture was then concentrated in vacuo to give the title compound (457 mg, 71%) as a white solid. ¾ NMR (CDC13) δ 7.30-7.23 (m, 2H), 7.20-7.13 (m, 2H), 4.78-4.69 (m, 1H), 4.56-4.45 (m, 1H), 4.43-4.35 (m, 1H), 3.87 (s, 3H), 3.49-3.43 (m, 2H); MS(ESI+) m/z 192.1 (M+H)+.
  • 3
  • [ 74163-81-8 ]
  • [ 2133-34-8 ]
  • (7aS,15aS)-8,13,15a,16-tetrahydropyrazino[1,2-b:4,5-b']diisoquinoline-7,15(5H,7aH)-dione [ No CAS ]
  • (4aS,12aS)-1,5,10,12a-tetrahydroazeto[1',2':4,5]pyrazino[1,2-b]isoquinoline-4,12(2H,4aH)-dione [ No CAS ]
 

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