4-ethyl-4,6,7,8-tetrahydro-1H-pyrano[3,4-f]indolizine-3,10-dione

Base Information

• Chemical Name: 4-ethyl-4,6,7,8-tetrahydro-1H-pyrano[3,4-f]indolizine-3,10-dione
• CAS No.: 43083-10-9
• Molecular Formula: C₁₃H₁₅NO₃
• Molecular Weight: 233.267
• NSC Number: 177364
• DSSTox Substance ID: DTXSID60306530
• Mol file: 43083-10-9.mol

Synonyms:43083-10-9;4-ethyl-4,6,7,8-tetrahydro-1H-pyrano[3,4-f]indolizine-3,10-dione;NSC177364;DTXSID60306530;NSC-177364;A934071

Chemical Property of 4-ethyl-4,6,7,8-tetrahydro-1H-pyrano[3,4-f]indolizine-3,10-dione

Chemical Property:

• Vapor Pressure: 4.09E-12mmHg at 25°C
• Boiling Point: 549.3±50.0 °C(Predicted)
• PKA: -1.28±0.40(Predicted)
• Density: 1.29±0.1 g/cm3(Predicted)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 233.10519334
• Heavy Atom Count: 17
• Complexity: 461

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1C2=C(COC1=O)C(=O)N3CCCC3=C2

Technology Process of 4-ethyl-4,6,7,8-tetrahydro-1H-pyrano[3,4-f]indolizine-3,10-dione

There total 7 articles about 4-ethyl-4,6,7,8-tetrahydro-1H-pyrano[3,4-f]indolizine-3,10-dione 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: 53.0%

4-ethyl-3,10-dioxo-1H,3H,4H,6H,7H,8H,10H-pyrano[3,4-f]indolizine-5-carboxylic acid methyl ester (145474-08-4) → 4-ethyl-1,6,7,8-tetrahydro-10H-pyrano[3,4-f]indolizine-3,10(4H)-dione (43083-10-9)

Guidance literature:

With hydrogen bromide; at 105 ℃; for 18h;

DOI:10.1021/jo00055a012

Reference yield:

5,6-dibromo-4-ethyl-1,6,7,8-tetrahydro-4H-pyrano[3,4-f]indolizine-3,10-dione (40163-24-4) → 4-ethyl-1,6,7,8-tetrahydro-10H-pyrano[3,4-f]indolizine-3,10(4H)-dione (43083-10-9)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In ethanol;

DOI:10.1021/jo00917a005

Reference yield:

2-(6-acetoxymethyl-1,8-dibromo-5-oxo-1,2,3,5-tetrahydro-indolizin-7-yl)-butyric acid methyl ester (43083-06-3) → 4-ethyl-1,6,7,8-tetrahydro-10H-pyrano[3,4-f]indolizine-3,10(4H)-dione (43083-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. H₂SO₄ / 1,2-dimethoxy-ethane

2: H₂, Et₃N / Pd-C / ethanol

With sulfuric acid; hydrogen; triethylamine; palladium on activated charcoal; In 1,2-dimethoxyethane; ethanol;

DOI:10.1021/jo00917a005

upstream raw materials:

5,6-dibromo-4-ethyl-1,6,7,8-tetrahydro-4H-pyrano[3,4-f]indolizine-3,10-dione

4-ethyl-3,10-dioxo-1H,3H,4H,6H,7H,8H,10H-pyrano[3,4-f]indolizine-5-carboxylic acid methyl ester

dimethyl 3-chloro-2-pentenedioate

methyl 7-methoxycarbonylmethyl-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate

Downstream raw materials:

4-ethyl-4-hydroxy-1,6,7,8-tetrahydro-10H-pyrano[3,4-f]indolizine-3,10(4H)-dione

camptothecin

4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione