Ethyl Indolizine-2-carboxylate

Base Information

• Chemical Name: Ethyl Indolizine-2-carboxylate
• CAS No.: 153274-63-6
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• DSSTox Substance ID: DTXSID30460133
• Nikkaji Number: J957.852H
• Wikidata: Q82284063
• Mol file: 153274-63-6.mol

Synonyms:Ethyl Indolizine-2-carboxylate;153274-63-6;2-Indolizinecarboxylicacid, ethyl ester;EthylIndolizine-2-carboxylate;SCHEMBL16739572;DTXSID30460133;QGWGRWMQFFGAQV-UHFFFAOYSA-N;2-Indolizinecarboxylicacid,ethyl ester;AKOS006321623

Chemical Property of Ethyl Indolizine-2-carboxylate

Chemical Property:

• Refractive Index: 1.564
• PSA: 30.71000
• Density: 1.13 g/cm³
• LogP: 2.11600
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

2-INDOLIZINECARBOXYLIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN2C=CC=CC2=C1

Technology Process of Ethyl Indolizine-2-carboxylate

There total 7 articles about Ethyl Indolizine-2-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: 75.0%

ethyl 2-(acetoxy(pyridin-2-yl)methyl)acrylate (153274-58-9) → ethyl (indolizine-2-carboxylate) (153274-63-6)

Guidance literature:

at 120 ℃; for 0.916667h; Inert atmosphere;

Reference yield: 67.0%

ethyl 3-hydroxy-2-methylene-3-(pyrid-2-yl)propanoate (153274-52-3) → ethyl (indolizine-2-carboxylate) (153274-63-6)

Guidance literature:

In acetic anhydride; at 130 ℃; for 0.75h; Microwave irradiation;

Reference yield:

pyridine-2-carbaldehyde (1121-60-4) → ethyl (indolizine-2-carboxylate) (153274-63-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,4-diaza-bicyclo[2.2.2]octane / 12 h / 20 °C / Sonication

2: pyridine / dichloromethane / 1.17 h / 0 - 20 °C / Inert atmosphere

3: toluene / 12 h / Reflux

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; toluene;

DOI:10.1021/jo502471q

upstream raw materials:

ethyl 2-(acetoxy(pyridin-2-yl)methyl)acrylate

ethyl 3-hydroxy-2-methylene-3-(pyrid-2-yl)propanoate

α-picoline

ethyl Bromopyruvate

Downstream raw materials:

3-phenyl-indolizine-2-carboxylic acid ethyl ester

ethyl 3-(2-chlorobenzyl)indolizine-2-carboxylate

C₂₀H₂₂N₂O₂

C₂₀H₂₂N₂O₂

Refernces

• 1、 Ni, Qijian,Zhu, Zhiming,Fan, Yanjun,Chen, Xiaoyun,Song, Xiaoxiao. "Chiral Phosphoric Acid Catalyzed Desymmetrization of Cyclopentendiones via Friedel–Crafts Conjugate Addition of Indolizines". supporting information. p. 9548 - 9553. Retrieved 2021/12/14.
• 2、 -. "INDOLIZINE-BASED DYES FOR DYE-SENSITIZED SOLAR CELL". Page/Page column 33; 35. . Retrieved 2016/04/01.