Diethyl 2-vinylcyclopropane-1,1-dicarboxylate

Base Information

• Chemical Name: Diethyl 2-vinylcyclopropane-1,1-dicarboxylate
• CAS No.: 7686-78-4
• Molecular Formula: C11H16O4
• Molecular Weight: 212.246
• Hs Code.: 2917209090
• European Community (EC) Number: 231-695-0
• DSSTox Substance ID: DTXSID90998169
• Nikkaji Number: J326.519F
• Mol file: 7686-78-4.mol

Synonyms:7686-78-4;Diethyl 2-vinylcyclopropane-1,1-dicarboxylate;diethyl 2-ethenylcyclopropane-1,1-dicarboxylate;2-Vinylcyclopropane-1,1-dicarboxylic acid diethyl ester;EINECS 231-695-0;MFCD00196937;1,1-Cyclopropanedicarboxylic acid, 2-ethenyl-, diethyl ester;ghl.PD_Mitscher_leg0.115;SCHEMBL1412659;2-VINYLCYCLOPROPANE-1,1-DICARBOXYLICACIDDIETHYLESTER;DTXSID90998169;Diphenylmethylene-GlycineMethylester;AKOS024322252;1,1-diethoxycarbonyl-2-vinylcyclopropane;DS-11899;SY242781;1,1-di-ethoxycarbonyl-2-vinylcyclopropane;1,1-bis-ethoxycarbonyl-2-vinylcyclopropane;1,1-bis(ethoxycarbonyl)-2-vinylcyclopropane;A9980;CS-0060000;Diethyl2-vinylcyclopropane-1,1-dicarboxylate;FT-0724591;diethyl 1-vinylcyclopropane-2,2-dicarboxylate;EN300-187817;Diethyl 2-vinyl-1,1-cyclopropanedicarboxylate #;1,1-diethyl 2-ethenylcyclopropane-1,1-dicarboxylate;2-vinyl-cyclopropane-1,1-dicarboxylic acid diethyl ester;1,1-Cyclopropanedicarboxylicacid,2-ethenyl-,1,1-diethyl ester

Chemical Property of Diethyl 2-vinylcyclopropane-1,1-dicarboxylate

Chemical Property:

• Vapor Pressure: 0.0652mmHg at 25°C
• Refractive Index: 1.528
• Boiling Point: 230.6 °C at 760 mmHg
• Flash Point: 101.6 °C
• PSA: 52.60000
• Density: 1.174 g/cm³
• LogP: 1.30490
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 212.10485899
• Heavy Atom Count: 15
• Complexity: 264

Purity/Quality:

99%, ^*data from raw suppliers

Diethyl2-Vinylcyclopropane-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(CC1C=C)C(=O)OCC
• Uses: Diethyl 2-Vinylcyclopropane-1,1-dicarboxylate used in the preparation of Vigabatri which is a novel anti-epileptic drug. Antidepressant; antipsychotic; anxiolytic.

Technology Process of Diethyl 2-vinylcyclopropane-1,1-dicarboxylate

There total 23 articles about Diethyl 2-vinylcyclopropane-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: 95.0%

1,4-dibromo-2-butene (6974-12-5) + diethyl malonate (105-53-3) → diethyl 2-vinylcyclopropane-1,1-dicarboxylate (7686-78-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 78 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chem.201406496

Reference yield: 88.0%

(E)-1,4-dibromobutene (821-06-7) + diethyl malonate (105-53-3) → diethyl 2-vinylcyclopropane-1,1-dicarboxylate (7686-78-4)

Guidance literature:

diethyl malonate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

(E)-1,4-dibromobutene; In tetrahydrofuran; at 0 - 70 ℃; Inert atmosphere;

DOI:10.1039/c3ra23291c

Reference yield: 78.0%

trans-1,4-dichlorobut-2-ene (110-57-6) + diethyl malonate (105-53-3) → diethyl 2-vinylcyclopropane-1,1-dicarboxylate (7686-78-4)

Guidance literature:

With sodium ethanolate; In ethanol;

DOI:10.1246/bcsj.56.2784

upstream raw materials:

sodium diethylmalonate

ethanol

(E)-1,4-dibromobutene

sodium diethylmalonate

Downstream raw materials:

2-phenol

[(C₆H₅CHCHCHCH₂CH(CO₂C₂H₅)CO₂C₂H₅)PdCl]2

Refernces

• 1、 Sarker, Prodip,Rehman, Saif U. R.,Rimmer, Stephen. "A macromonomer approach to the synthesis of poly(1,1-bis(ethoxycarbonyl)-2- vinyl cyclopropane-graft-dimethyl siloxane)". . p. 1822 - 1830. Retrieved 2013.
• 2、 Galli,Gasperetti,Bertolucci,Chiellini. "New fluorinated liquid crystalline copoly(vinylcyclopropane)s with unusual macromolecular structure". . p. 413/[1455]-419/[1461]. Retrieved 2004.
• 3、 Karumanchi, Kishore,Natarajan, Senthil Kumar,Gadde, Sunil,Vanchanagiri, Krishna. "A convenient approach for vinylation reaction in the synthesis of 5-vinyl-2-pyrrolidinone, a key intermediate of vigabatrin". . p. 2035 - 2039. Retrieved 2020/01/02.
• 4、 Pan, Dingwu,Mou, Chengli,Zan, Ningning,Lv, Ya,Song, Bao-An,Chi, Yonggui Robin,Jin, Zhichao. "NaOH-Promoted Chemoselective Cascade Cyclization of Cyclopropyl Esters with Unsaturated Imines: Access to Bioactive Cyclopenta[c]pyridine Derivatives". supporting information. p. 6624 - 6627. Retrieved 2019/09/07.