3-Ethoxycyclopent-2-en-1-one

Base Information

• Chemical Name: 3-Ethoxycyclopent-2-en-1-one
• CAS No.: 22627-70-9
• Molecular Formula: C7H10 O2
• Molecular Weight: 126.155
• Hs Code.: 2914509090
• European Community (EC) Number: 245-138-4
• DSSTox Substance ID: DTXSID00177165
• Nikkaji Number: J286.265D
• Wikidata: Q83047479
• Mol file: 22627-70-9.mol

Synonyms:22627-70-9;3-Ethoxycyclopent-2-en-1-one;3-Ethoxy-2-cyclopentenone;3-ethoxy-2-cyclopenten-1-one;3-ethoxycyclopent-2-enone;EINECS 245-138-4;2-Cyclopenten-1-one, 3-ethoxy-;3-ethoxycyclopentenone;3-ethoxy cyclopentenone;3-Ethoxy-cyclopent-2-enone;3-ethoxy-2-cyclopenten-1-on;SCHEMBL1021859;DTXSID00177165;3-Ethoxy-2-cyclopentenone, 98%;XAA62770;MFCD00042963;AKOS015916243;AS-58541;CS-0039741;FT-0709397;EN300-137209;W16153;J-014788

Chemical Property of 3-Ethoxycyclopent-2-en-1-one

Chemical Property:

• Vapor Pressure: 0.0684mmHg at 25°C
• Refractive Index: n20/D 1.492(lit.)
• Boiling Point: 229.7°Cat760mmHg
• Flash Point: 101.8°C
• PSA: 26.30000
• Density: 1.03g/cm³
• LogP: 1.26970
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Methanol (Sparingly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 126.068079557
• Heavy Atom Count: 9
• Complexity: 147

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Ethoxy-2-cyclopentenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC(=O)CC1
• Uses: 3-Ethoxy-2-cyclopentenone (3-Ethoxy-2-cyclopenten-1-one) may be used as a starting material in the synthesis of the following:allylic cyclopentenyl alcohols like 2-cyclopentenol, 3-methyl-2-cyclopentenol and 3-methoxymethaoxymethyl-2-cyclopentenol3-aminocyclopent-2-en-1-one(E)-5-(((2S*,3S*)-3-((benzyloxy)methyl)oxiran-2- yl)methylene)-3-ethoxycyclopent-2-enone, an γ,δ -epoxy-α,β-unsaturated cyclic enone

Technology Process of 3-Ethoxycyclopent-2-en-1-one

There total 4 articles about 3-Ethoxycyclopent-2-en-1-one 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: 99.0%

1,3-cyclopentadione (3859-41-4) + ethanol (64-17-5) → 3-ethoxycyclopent-2-en-1-one (22627-70-9)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 90 ℃; for 10h;

DOI:10.1002/anie.201700837

Reference yield: 3.0%

1,3-cyclopentadione (3859-41-4) + 2-amino-5-bromobenzophenone (39859-36-4) → 7-bromo-9-phenyl-2,3-dihydro-cyclopenta[b]quinolin-1-one + 3-ethoxycyclopent-2-en-1-one (22627-70-9)

Guidance literature:

sodium tetrachloroaurate dihydrate; In ethanol; at 80 ℃; for 48h; Title compound not separated from byproducts;

DOI:10.1016/j.tet.2007.01.050

Reference yield:

ethyl bromide (74-96-4) + GENERIC INORGANIC CATION; 3-oxo-cyclopent-1-enolate → 3-ethoxycyclopent-2-en-1-one (22627-70-9)

Guidance literature:

DOI:10.1139/v73-127

upstream raw materials:

1,3-cyclopentadione

ethanol

ethyl bromide

maleic anhydride

Downstream raw materials:

3-<(benzyloxy)methyl>-2-cyclopentene-1-one

3-isopropyl-cyclopent-2-enone

5-{3-[(Dimethyl-phenyl-silanyl)-methyl]-2-methyl-cyclopent-2-enylmethyl}-3-ethoxy-cyclopent-2-enone

(+/-)-5-<<3-<(dimethylphenylsilyl)methyl>-2-methyl-2-cyclopenten-1-yl>hydroxymethyl>-3-ethoxy-2-cyclopenten-1-one

Refernces

• 1、 Wang, Hong-Shuang,Li, Hui-Jing,Wang, Jun-Li,Wu, Yan-Chao. "Protecting-group-free synthesis of haterumadienone- and puupehenone-type marine natural products". . p. 2140 - 2144. Retrieved 2017.
• 2、 Lang, Qiwei,Yang, Huaxin,Gu, Guoxian,Feng, Qiang,Wen, Jialin,Zhang, Xumu. "Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?". supporting information. p. 933 - 936. Retrieved 2021/03/03.
• 3、 Delayre, Bastien,Piemontesi, Cyril,Wang, Qian,Zhu, Jieping. "TiCl3-Mediated Synthesis of 2,3,3-Trisubstituted Indolenines: Total Synthesis of (+)-1,2-Dehydroaspidospermidine, (+)-Condyfoline, and (?)-Tubifoline". supporting information. p. 13990 - 13997. Retrieved 2020/06/10.