Diethyl formamido[(1H-indol-3-yl)methyl]propanedioate

Base Information

• Chemical Name: Diethyl formamido[(1H-indol-3-yl)methyl]propanedioate
• CAS No.: 64258-95-3
• Molecular Formula: C17H20 N2 O5
• Molecular Weight: 332.356
• NSC Number: 157806
• DSSTox Substance ID: DTXSID90303310
• Wikidata: Q82048507
• Mol file: 64258-95-3.mol

Synonyms:64258-95-3;NSC157806;SCHEMBL838321;Diethyl formamido[(1H-indol-3-yl)methyl]propanedioate;DTXSID90303310;ZAIGSUKBOXJYBT-UHFFFAOYSA-N;NSC-157806;2-Formamido-3-(3-indolyl)-2-carbethoxypropionic acid ethyl ester

Chemical Property of Diethyl formamido[(1H-indol-3-yl)methyl]propanedioate

Chemical Property:

• Vapor Pressure: 3.17E-13mmHg at 25°C
• Boiling Point: 575°C at 760 mmHg
• Flash Point: 301.6°C
• Density: 1.261g/cm³
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 332.13722174
• Heavy Atom Count: 24
• Complexity: 450

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CC1=CNC2=CC=CC=C21)(C(=O)OCC)NC=O

Technology Process of Diethyl formamido[(1H-indol-3-yl)methyl]propanedioate

There total 8 articles about Diethyl formamido[(1H-indol-3-yl)methyl]propanedioate 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:

indole (120-72-9) → ethyl 2-formamido-3-(3-indolyl)-2-carbethoxypropionate (64258-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. AcOH / 20 °C

2: NaOH / toluene / Heating

With sodium hydroxide; acetic acid; In toluene;

DOI:10.1016/j.bmcl.2005.07.077

Reference yield:

indole (120-72-9) + formylamino-piperidinomethyl-malonic acid diethyl ester (202979-89-3) → ethyl 2-formamido-3-(3-indolyl)-2-carbethoxypropionate (64258-95-3)

Guidance literature:

With sodium hydroxide; xylene;

DOI:10.1021/ja01115a016

Reference yield:

3-(Dimethylaminomethyl)indole (87-52-5) + diethyl 2-formylaminomalonate (6326-44-9) → ethyl 2-formamido-3-(3-indolyl)-2-carbethoxypropionate (64258-95-3)

Guidance literature:

With sodium ethanolate; dimethyl sulfate; Yield given. Multistep reaction; 2.) ethanol, 2.) room temp., 4 h;

DOI:10.1021/jo00270a029

upstream raw materials:

indole

formylamino-piperidinomethyl-malonic acid diethyl ester

N-[(1H-indol-3-yl)methyl]-N-ethylethanamine

diethyl 2-formylaminomalonate

Downstream raw materials:

2-Benzoylamino-2-(2-formyl-1H-indol-3-ylmethyl)-malonic acid diethyl ester

2-benzoyl-3,3-dicarbethoxy-1,2,3,4-tetrahydro-β-carboline

2-amino-3-(1-methyl-1H-indol-3-yl)-propanoic acid

Trp

Refernces

• 1、 Teng, Xin,Degterev, Alexei,Jagtap, Prakash,Xing, Xuechao,Choi, Sungwoon,Denu, Regine,Yuan, Junying,Cuny, Gregory D.. "Structure-activity relationship study of novel necroptosis inhibitors". . p. 5039 - 5044. Retrieved 2007/10/03.
• 2、 Hagen, Timothy J.,Narayanan, Krishnaswamy,Names, Jeffrey,Cook, James M.. "DDQ Oxidations in the Indole Area. Synthesis of 4-Alkoxy-β-carbolines Including the Natural Products Crenatine and 1-Methoxycanthin-6-one". . p. 2170 - 2178. Retrieved 2007/10/02.