Benzyl 3-formyl-1H-indole-1-carboxylate

Base Information

• Chemical Name: Benzyl 3-formyl-1H-indole-1-carboxylate
• CAS No.: 74639-50-2
• Molecular Formula: C17H13NO3
• Molecular Weight: 279.295
• DSSTox Substance ID: DTXSID10547395
• Nikkaji Number: J1.818.397H
• Wikidata: Q82425588
• Mol file: 74639-50-2.mol

Synonyms:Benzyl 3-formyl-1H-indole-1-carboxylate;74639-50-2;BENZYL 3-FORMYLINDOLE-1-CARBOXYLATE;SCHEMBL9027466;DTXSID10547395;VWONFYRSPSSXJO-UHFFFAOYSA-N;N-Carbobenzoxy-indole-3-carboxaldehyde;3-Formyl-indole-1-carboxylic acid benzyl ester

Chemical Property of Benzyl 3-formyl-1H-indole-1-carboxylate

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 279.08954328
• Heavy Atom Count: 21
• Complexity: 378

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)N2C=C(C3=CC=CC=C32)C=O

Technology Process of Benzyl 3-formyl-1H-indole-1-carboxylate

There total 2 articles about Benzyl 3-formyl-1H-indole-1-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: 100.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonyl-indole-3-carbaldehyde (74639-50-2)

Guidance literature:

With dmap; sodium carbonate; In water; acetonitrile; at 20 ℃; for 24h;

DOI:10.1246/bcsj.75.2517

Reference yield:

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + gold-brown oil + benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonyl-indole-3-carbaldehyde (74639-50-2)

Guidance literature:

In tetrahydrofuran;

Reference yield: 85.0%

methylmagnesium bromide (75-16-1) + N-benzyloxycarbonyl-indole-3-carbaldehyde (74639-50-2) → 1-(N-carbobenzoxyindol-3-yl)ethanol (103871-31-4,105517-85-9)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 ℃; for 2h;

DOI:10.1021/jo00375a030

upstream raw materials:

Indole-3-carboxaldehyde

benzyl chloroformate

Downstream raw materials:

trans-2-(1-benzyloxycarbonylindol-3-yl)-4-benzyloxymethyl-1,3-dioxolane

cis-2-(1-benzyloxycarbonylindol-3-yl)-4-benzyloxymethyl-1,3-dioxolane

1-(N-carbobenzoxyindol-3-yl)ethanol

3-[(2R,3S)-3,4-Dimethyl-5,7-dioxo-2-phenyl-[1,4]oxazepan-(6E)-ylidenemethyl]-indole-1-carboxylic acid benzyl ester