(R)-1,2,3,4-Tetrahydro-6-hydroxy-3-isoquinolinecarboxylic acid

Base Information

• Chemical Name: (R)-1,2,3,4-Tetrahydro-6-hydroxy-3-isoquinolinecarboxylic acid
• CAS No.: 134388-87-7
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.202
• Hs Code.: 29334990
• DSSTox Substance ID: DTXSID20928595
• Nikkaji Number: J1.063.441E
• Mol file: 134388-87-7.mol

Synonyms:DTXSID20928595;(R)-1,2,3,4-Tetrahydro-6-hydroxy-3-isoquinolinecarboxylic acid

Chemical Property of (R)-1,2,3,4-Tetrahydro-6-hydroxy-3-isoquinolinecarboxylic acid

Chemical Property:

• Vapor Pressure: 4.06E-09mmHg at 25°C
• Melting Point: 256-260 °C
• Refractive Index: 1.612
• Boiling Point: 456.3 °C at 760 mmHg
• Flash Point: 229.8 °C
• PSA: 78.79000
• Density: 1.351 g/cm³
• LogP: 0.75560
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 193.07389321
• Heavy Atom Count: 14
• Complexity: 231

Purity/Quality:

98%min ^*data from raw suppliers

6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylicacid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NCC2=C1C=C(C=C2)O)C(=O)O
• Isomeric SMILES: C1[C@@H](NCC2=C1C=C(C=C2)O)C(=O)O

Technology Process of (R)-1,2,3,4-Tetrahydro-6-hydroxy-3-isoquinolinecarboxylic acid

There total 8 articles about (R)-1,2,3,4-Tetrahydro-6-hydroxy-3-isoquinolinecarboxylic acid 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: 100.0%

→ 6-hydroxy-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid (76824-99-2,134388-87-7)

Guidance literature:

Reference yield: 89.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + D/L-3-hydroxy-phenylalanine (775-06-4,29562-33-2) → 6-hydroxy-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid (76824-99-2,134388-87-7)

Guidance literature:

With water; at 20 ℃;

DOI:10.1016/j.bmcl.2005.03.075

Reference yield: 70.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + D/L-3-hydroxy-phenylalanine (775-06-4,29562-33-2) → 8-hydroxy-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid + 6-hydroxy-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid (76824-99-2,134388-87-7)

Guidance literature:

With hydrogenchloride; for 0.75h; Heating;

DOI:10.1021/jo00014a012

upstream raw materials:

formaldehyd

D/L-3-hydroxy-phenylalanine

rac-N-methyl-meta-tyrosine

6-hydroxy-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid

Downstream raw materials:

C₁₂H₁₁NO₃

methyl 6-hydroxyisoquinoline-3-carboxylate

2-(tert-butoxycarbonyl)-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

ethyl 6-hydroxy-2-(methoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Refernces

• 1、 Lahham, Majd,Pavkov-Keller, Tea,Fuchs, Michael,Niederhauser, Johannes,Chalhoub, Gabriel,Daniel, Bastian,Kroutil, Wolfgang,Gruber, Karl,Macheroux, Peter. "Oxidative cyclization of N-methyl-dopa by a fungal flavoenzyme of the amine oxidase family". . p. 17021 - 17032. Retrieved 2018.
• 2、 Ju, Shuyun,Qian, Mingxin,Xu, Gang,Yang, Lirong,Wu, Jianping. "Chemoenzymatic Approach to (S)-1,2,3,4-Tetrahydroisoquinoline Carboxylic Acids Employing D-Amino Acid Oxidase". . p. 3191 - 3199. Retrieved 2019.