2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester
• CAS No.: 17447-60-8
• Molecular Formula: C9H12 O4
• Molecular Weight: 184.192
• European Community (EC) Number: 865-426-9
• DSSTox Substance ID: DTXSID60440307
• Nikkaji Number: J452.776C
• Mol file: 17447-60-8.mol

Synonyms:17447-60-8;2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester;dimethyl 2-vinylcyclopropane-1,1-dicarboxylate;Dimethyl 2-ethenylcyclopropane-1,1-dicarboxylate;1,1-Cyclopropanedicarboxylic acid, 2-ethenyl-, 1,1-dimethyl ester;1-vinyl-2,2-dicarbomethoxy cyclopropane;1,1-DIMETHYL 2-ETHENYLCYCLOPROPANE-1,1-DICARBOXYLATE;SCHEMBL812061;DTXSID60440307;BTHUKAQVHWDTAH-UHFFFAOYSA-N;AKOS006327686;AS-71996;dimethyl-2-vinylcyclopropane-1,1-dicarboxylate;EN300-176536;1,1-DIMETHYL2-ETHENYLCYCLOPROPANE-1,1-DICARBOXYLATE;2-vinyl cyclopropane-1,1-dicarboxylic acid dimethyl ester;2-vinyl-cyclopropane-1,1-dicarboxylic acid dimethyl ester

Chemical Property of 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester

Chemical Property:

• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Ethyl Acetate; Dichloromethane
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 184.07355886
• Heavy Atom Count: 13
• Complexity: 240

Purity/Quality:

99% ^*data from raw suppliers

2-VINYLCYCLOPROPANE-1,1-DICARBOXYLIC ACID DIMETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1(CC1C=C)C(=O)OC
• Uses: 1,1-Dimethyl 2-Ethenylcyclopropane-1,1-dicarboxylate is a useful chemical in organic synthesis.

Technology Process of 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester

There total 22 articles about 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester 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: 94.0%

2-(2-Hydroxy-1-trimethylsilanyl-ethyl)-cyclopropane-1,1-dicarboxylic acid dimethyl ester (166302-33-6) → dimethyl 2-vinylcyclopropane-1,1-dicarboxylate (17447-60-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/0040-4039(94)88396-3

Reference yield: 90.0%

(E)-1,4-dibromobutene (821-06-7) + malonic acid dimethyl ester (108-59-8) → dimethyl 2-vinylcyclopropane-1,1-dicarboxylate (17447-60-8)

Guidance literature:

With sodium methylate; In methanol; for 2.5h; Reflux; Inert atmosphere;

DOI:10.1002/ejoc.201600582

Reference yield: 85.0%

trans-1,4-dichlorobut-2-ene (110-57-6) + malonic acid dimethyl ester (108-59-8) → dimethyl 2-vinylcyclopropane-1,1-dicarboxylate (17447-60-8)

Guidance literature:

With sodium methylate; In methanol; 1.) RT, 45 min; 2.) 50 deg C, 3 h;

DOI:10.1246/cl.1984.1795

upstream raw materials:

dimethyl diazomalonate

buta-1,3-diene

1,4-dichloro-2-butene

malonic acid dimethyl ester

Downstream raw materials:

1,1-dimethoxycarbonyl-3-methyl-3-p-toluenesulfonyl-4-vinylcyclopentane

2-((E)-5,5-Bis-benzenesulfonyl-pent-2-enyl)-malonic acid dimethyl ester

(4E,9E)-7,7-Bis-benzenesulfonyl-2,12-bis-methoxycarbonyl-trideca-4,9-dienedioic acid dimethyl ester

dimethyl 2-[2-(3-allyl-1-benzyl-1H-indol-2-yl)-3-butenyl]malonate

Refernces

• 1、 Yuan, Zhenbo,Wei, Weiwei,Lin, Aijun,Yao, Hequan. "Bifunctional Organo/Metal Cooperatively Catalyzed [3 + 2] Annulation of para-Quinone Methides with Vinylcyclopropanes: Approach to Spiro[4.5]deca-6,9-diene-8-ones". . p. 3370 - 3373. Retrieved 2016.
• 2、 Parsons, Andrew T.,Campbell, Matthew J.,Johnson, Jeffrey S.. "Diastereoselective synthesis of tetrahydrofurans via palladium(0)-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes and aldehydes". . p. 2541 - 2544. Retrieved 2008.
• 3、 Chiba, Shunsuke,Li, Haoyu,Liu, Yuliang. "Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis". supporting information. p. 6264 - 6267. Retrieved 2021/07/02.