(3S)-1,2,3,4-tetrahydroisoquinolin-2-ium-3-carboxylate

Base Information

• Chemical Name: (3S)-1,2,3,4-tetrahydroisoquinolin-2-ium-3-carboxylate
• CAS No.: 74163-81-8
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• Hs Code.: 29334900
• Mol file: 74163-81-8.mol

Synonyms:

Chemical Property of (3S)-1,2,3,4-tetrahydroisoquinolin-2-ium-3-carboxylate

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 5.62E-07mmHg at 25°C
• Melting Point: 300 °C
• Refractive Index: -166 ° (C=1, 1mol/L NaOH)
• Boiling Point: 372 °C at 760 mmHg
• PKA: 2.21±0.20(Predicted)
• Flash Point: 178.8 °C
• PSA: 49.33000
• Density: 1.225 g/cm³
• LogP: 1.11430
• Storage Temp.: Store at 0-5°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 200

Purity/Quality:

99% ^*data from raw suppliers

(S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C([NH2+]CC2=CC=CC=C21)C(=O)[O-]
• Isomeric SMILES: C1[C@H]([NH2+]CC2=CC=CC=C21)C(=O)[O-]
• Description: (S)-(-)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid is a quinoline derivative, which is used as an intermediate in the synthesis of quinapril. Quinapril, a product developed by Pfizer, was approved by the US FDA in 1991 for the treatment of hypertension, congestive heart failure and angioedema.

Technology Process of (3S)-1,2,3,4-tetrahydroisoquinolin-2-ium-3-carboxylate

There total 22 articles about (3S)-1,2,3,4-tetrahydroisoquinolin-2-ium-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → L-Tic-OH (74163-81-8)

Guidance literature:

With hydrogenchloride; In water; at 90 ℃; for 12h;

DOI:10.1039/c6tb02705a

Reference yield: 94.0%

(-)-menthyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (143767-56-0) → L-Tic-OH (74163-81-8)

Guidance literature:

With sodium hydroxide; In methanol; for 6h; Ambient temperature;

DOI:10.1055/s-1992-26325

Reference yield: 81.0%

(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester (77497-96-2) → L-Tic-OH (74163-81-8)

Guidance literature:

With sodium hydroxide; In water; for 15h; Ambient temperature;

DOI:10.1055/s-1992-26325

upstream raw materials:

formaldehyd

L-phenylalanine

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

(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester

Downstream raw materials:

(S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester

(10aS)-10,10a-dihydro[1,3]oxazolo[3,4-b]isoquinoline-1,3(5H)-dione

(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride

(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

Refernces

• 1、 -. "Novel isoquinoline-oxazoline chiral ligand and preparation and application thereof (by machine translation)". Paragraph 0021-0022; 0024. . Retrieved 2020/06/20.
• 2、 Li, Wei,Wang, Guotong,Lai, Jixing,Li, Shengkun. "Multifunctional isoquinoline-oxazoline ligands of chemical and biological importance". supporting information. p. 5902 - 5905. Retrieved 2019/05/27.