Rhetsinine

Base Information

• Chemical Name: Rhetsinine
• CAS No.: 526-43-2
• Molecular Formula: C19H17N3O2
• Molecular Weight: 319.363
• Hs Code.: 2933990090
• NSC Number: 258315
• UNII: YQ7LSR9JJA
• DSSTox Substance ID: DTXSID30200576
• Nikkaji Number: J11.873G
• Wikidata: Q72506086
• Metabolomics Workbench ID: 140561
• ChEMBL ID: CHEMBL508030
• Mol file: 526-43-2.mol

Synonyms:hydroxyevodiamine;N2-(2-methylaminobenzoyl)tetrahydro-1H-pyrido(3,4-b)indol-1-one;rhetsinine

Chemical Property of Rhetsinine

Chemical Property:

• Vapor Pressure: 8.44E-15mmHg at 25°C
• Boiling Point: 609.5°C at 760 mmHg
• PKA: 14.94±0.20(Predicted)
• Flash Point: 322.4°C
• PSA: 65.20000
• Density: 1.372±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 3.05920
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 319.132076794
• Heavy Atom Count: 24
• Complexity: 509

Purity/Quality:

95%-98% ^*data from raw suppliers

Hydroxyevodiamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=CC=CC=C1C(=O)N2CCC3=C(C2=O)NC4=CC=CC=C34

Technology Process of Rhetsinine

There total 10 articles about Rhetsinine 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: 87.0%

evodiamine → N2-2-methylaminobenzoyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one (526-43-2)

Guidance literature:

With dipotassium peroxodisulfate; water; tetramethlyammonium chloride; In dimethyl sulfoxide; at 40 ℃; for 7h;

DOI:10.1021/acs.orglett.9b02772

Reference yield: 27.0%

1,2,3,4-tetrahydronorharman-1-one (17952-82-8) + Methyl N-methylanthranilate (85-91-6) → N2-2-methylaminobenzoyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one (526-43-2)

Guidance literature:

1,2,3,4-tetrahydronorharman-1-one; With trichlorophosphate; In tetrahydrofuran; at 60 ℃; for 3h; Inert atmosphere;

Methyl N-methylanthranilate; In tetrahydrofuran; at 75 ℃; for 96h; Further stages; Inert atmosphere;

DOI:10.1016/j.tet.2016.03.059

Reference yield:

isatoic anhydride (118-48-9) → N2-2-methylaminobenzoyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one (526-43-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 0.17 h

1.2: 16 h / 45 °C

2.1: dichloromethane / Heating

3.1: potassium permanganate / acetone / 3 h / 60 °C

With potassium permanganate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl acetamide; acetone;

DOI:10.1016/j.tet.2016.03.059

upstream raw materials:

1,2,3,4-tetrahydronorharman-1-one

Methyl N-methylanthranilate

3,4-dihydro-β-carboline

isatoic anhydride

Downstream raw materials:

evodiamine

1,2,3,4-tetrahydronorharman-1-one

N-Methylanthranilic acid

13b-hydroxyevodiamine

Refernces

• 1、 Wehle, Sarah,Espargaró, Alba,Sabaté, Raimon,Decker, Michael. "Investigation into the stability and reactivity of the pentacyclic alkaloid dehydroevodiamine and the benz-analog thereof". . p. 2535 - 2543. Retrieved 2016/04/26.