Diethyl 3-cyclopentene-1,1-dicarboxylate

Base Information

• Chemical Name: Diethyl 3-cyclopentene-1,1-dicarboxylate
• CAS No.: 21622-00-4
• Molecular Formula: C11H16O4
• Molecular Weight: 212.246
• Hs Code.: 2917209090
• European Community (EC) Number: 847-980-3
• Nikkaji Number: J698.496G
• Mol file: 21622-00-4.mol

Synonyms:21622-00-4;DIETHYL 3-CYCLOPENTENE-1,1-DICARBOXYLATE;Diethyl cyclopent-3-ene-1,1-dicarboxylate;CYCLOPENT-3-ENE-1,1-DICARBOXYLIC ACID DIETHYL ESTER;3-Cyclopentene-1,1-dicarboxylic acid, diethyl ester;MFCD04115567;Diethyl3-Cyclopentene-1,1-dicarboxylate;SCHEMBL609526;AYKIAWRITOYVSR-UHFFFAOYSA-N;BCP24338;diethyl-3-cyclopentene dicarboxylate;AKOS014688622;AB20250;CS-W001503;CS-11312;diethyl-3-cyclopentene-1,1-dicarboxylate;SY015514;diethyl cyclopent-3-ene-1,1 -dicarboxylate;FT-0743169;Diethyl Cyclopent-3-Ene-1, 1 -Dicarboxylate;EN300-187085;3-Cyclopentene-1,1-dicarboxylic acid diethyl ester;1,1-DIETHYL CYCLOPENT-3-ENE-1,1-DICARBOXYLATE

Chemical Property of Diethyl 3-cyclopentene-1,1-dicarboxylate

Chemical Property:

• PSA: 52.60000
• LogP: 1.44900
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 212.10485899
• Heavy Atom Count: 15
• Complexity: 252

Purity/Quality:

98%min ^*data from raw suppliers

Diethyl3-Cyclopentene-1,1-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CC=CC1)C(=O)OCC

Technology Process of Diethyl 3-cyclopentene-1,1-dicarboxylate

There total 12 articles about Diethyl 3-cyclopentene-1,1-dicarboxylate 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: 83.0%

diethyl 2-allyl-2-((4R,5R,E)-6-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-hydroxy-5-methyl-6-oxohex-2-enyl)malonate (1354716-14-5) → (S)-4-benzyl-3-((2R,3R)-3-hydroxy-2-methylpent-4-enoyl)-oxazolidin-2-one (1354716-10-1) + Cyclopent-3-ene-1,1-dicarboxylic acid diethyl ester (21622-00-4)

Guidance literature:

With Hoveyda-Blechert second generation catalyst; In ethene; toluene; at 60 ℃; for 12h; under 760.051 Torr; Inert atmosphere;

DOI:10.1021/jo202398q

Reference yield: 49.0%

Z-1,4-dichlorobutene (1476-11-5) + diethyl malonate (105-53-3) → diethyl 2-vinylcyclopropane-1,1-dicarboxylate (7686-78-4) + Cyclopent-3-ene-1,1-dicarboxylic acid diethyl ester (21622-00-4) + diethyl 2-[(2Z)-4-chlorobut-2-enyl]malonate

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In acetonitrile; Microwave irradiation;

DOI:10.1134/S1070363217010248

Reference yield: 45.0%

diallylmalonic acid diethyl ester (3195-24-2) → ethene (74-85-1) + Cyclopent-3-ene-1,1-dicarboxylic acid diethyl ester (21622-00-4)

Guidance literature:

With C₁₆H₄₀ClOP₂SiV; In chloroform-d1; at 22 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.organomet.1c00425

upstream raw materials:

Z-1,4-dichlorobutene

diethyl malonate

diallylmalonic acid diethyl ester

2-allyl-2-(2-benzenesulfonyl-5-phenyl-penta-2,3-dienyl)-malonic acid dimethyl ester

Downstream raw materials:

Dimethyl 3-cyclopentene-1,1-dicarboxylate

3-cyclopenten-1,1-dimethanol

ethyl 3-cyclopentene-1-carboxylate

cyclopentane-1,1-dicarboxylic acid diethyl ester

Refernces

• 1、 Dias, Eric L.,Nguyen, SonBinh T.,Grubbs, Robert H.. "Well-defined ruthenium olefin metathesis catalysts: Mechanism and activity". . p. 3887 - 3897. Retrieved 1997.
• 2、 Belov, Dmitry S.,Bukhryakov, Konstantin V.,Chakraborty, Indranil,Fenoll, Didac A.,Solans-Monfort, Xavier. "Synthesis of Vanadium Oxo Alkylidene Complex and Its Reactivity in Ring-Closing Olefin Metathesis Reactions". supporting information. p. 2939 - 2944. Retrieved 2021/09/13.
• 3、 Kim, Yaewon,Chen, Chia-Hsiu,Hilty, Christian. "Direct observation of Ru-alkylidene forming into ethylene in ring-closing metathesis from hyperpolarized 1H NMR". supporting information. p. 4333 - 4336. Retrieved 2018/05/07.