1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid

Base Information

• Chemical Name: 1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid
• CAS No.: 82789-27-3
• Molecular Formula: C₂₀H₂₀N₂O₄
• Molecular Weight: 352.39
• NSC Number: 96603
• DSSTox Substance ID: DTXSID301002888
• ChEMBL ID: CHEMBL1360719
• Mol file: 82789-27-3.mol

Synonyms:1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid;1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid;NSC96603;ChemDiv1_012723;CBDivE_003050;MLS000026887;SCHEMBL8323002;CHEMBL1360719;HMS623C07;DTXSID301002888;HMS2359A09;NSC-96603;STL477635;AKOS000542341;AKOS016037709;CCG-198443;1-(3,4-Dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid;NCGC00684588-01;SMR000122881;BRD-A92391350-001-09-6;1-(3,4-DIMETHOXYPHENYL)-1H,2H,3H,4H,9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLIC ACID

Chemical Property of 1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 8.67E-15mmHg at 25°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 352.14230712
• Heavy Atom Count: 26
• Complexity: 516

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2C3=C(CC(N2)C(=O)O)C4=CC=CC=C4N3)OC

Technology Process of 1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid

There total 2 articles about 1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic 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:

3,4-dimethoxy-benzaldehyde (120-14-9) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → 1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid (82789-27-3)

Guidance literature:

With acetic acid; for 3h; Reflux;

DOI:10.1039/c5md00312a

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) + Trp (54-12-6,27732-43-0,80206-30-0,27813-82-7) → 1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid (82789-27-3)

Guidance literature:

With acetic acid; for 3h; Reflux;

DOI:10.1016/j.ejmech.2018.02.003

Reference yield:

1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid (82789-27-3) → 9-butyl-1-(3,4-dimethoxyphenyl)-3-hydroxymethyl-β-carboline

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / 4 h / Reflux

2: sulfur / 5,5-dimethyl-1,3-cyclohexadiene / 8 h / Reflux

3: sodium hydride / N,N-dimethyl-formamide / 0.5 - 2 h / 20 °C

4: lithium borohydride / tetrahydrofuran / 9 h / 20 °C

With lithium borohydride; thionyl chloride; sodium hydride; sulfur; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide;

DOI:10.1039/c5md00312a

upstream raw materials:

3,4-dimethoxy-benzaldehyde

L-Tryptophan

Trp

Downstream raw materials:

ethyl 1-(3,4-dimethoxyphenyl)-9H-pyrido[3,4-b]-indole-3-carboxylate