Dimethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Base Information

• Chemical Name: Dimethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
• CAS No.: 3014-58-2
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23
• European Community (EC) Number: 678-762-4
• NSC Number: 46421,7326
• DSSTox Substance ID: DTXSID8041876
• Nikkaji Number: J15.129G
• Wikipedia: Dimethyl_carbate
• Mol file: 3014-58-2.mol

Synonyms:5826-73-3;Dimethyl 5-norbornene-2,3-dicarboxylate;Dimethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate;Dimethyl carbate;NISY;Dimelone;DIMALONE;3014-58-2;Dimethylkarbat;Compound 3,916;Dimethyl bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylate;Dimethyl bicyclo[2.2.1]-5-heptene-2,3-dicarboxylate;5-Norbornene-2,3-dicarboxylic acid, dimethyl ester;Dimethyl 5-bicyclo(2.2.1)hepten-2,3-dicarboxylate;Dimethyl 5-bicyclo[2.2.1]hepten-2,3-dicarboxylate;SCHEMBL147771;Dimethylester kyseliny bicyklo(2,2,1)hept-5-en-2,3-dikarboxylove;dimethyl bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylate;5-Norbornene-2, dimethyl ester;DTXSID8041876;NSC7326;NSC-7326;NSC46421;AKOS015840932;5-Norbornene-2, dimethyl ester, cis-;AS-79065;WLN: L55 A CUTJ EVO1 GVO1 -C;CS-0046190;FT-0625071;Bicyclo[2.2.1]hept-5-ene-2, dimethyl ester;F87448;endo-Methylenetetrahydrophthalic acid, dimethyl ester;Dimethyl bicyclo[2.2.1]-5-heptene-2,3 dicarboxylate;Dimethylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate;Dimethyl cis-bicyclo[2,1]-5-heptene-2,3-dicarboxylate;Dimethyl cis-bicyclo[2.2.1]-5-heptene-2,3-dicarboxylate;cis-Bicyclo[2,1]-heptene-2,3-dicarboxylic acid, methyl ester;2,3-DIMETHYL BICYCLO[2.2.1]HEPT-5-ENE-2,3-DICARBOXYLATE;cis-Bicyclo[2,1]hept-5-ene-2,3-dicarboxylic acid, dimethyl ester;cis-3,6-Endomethylene-.delta.(sup4)-tetrahydrophthalic acid dimethyl ester;endo,exo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester

Chemical Property of Dimethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Chemical Property:

• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 210.08920892
• Heavy Atom Count: 15
• Complexity: 291

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C2CC(C1C(=O)OC)C=C2

Technology Process of Dimethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

There total 31 articles about Dimethyl bicyclo[2.2.1]hept-5-ene-2,3-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: 99.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + dimethylfumarate (624-49-7) → dimethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (3014-58-2,5826-73-3,7184-07-8,39589-98-5,116404-47-8,117604-28-1,135357-64-1)

Guidance literature:

Reference yield: 98.0%

bi(cyclopentadiene) (77-73-6,933-60-8,1755-01-7,25038-78-2) + dimethylfumarate (624-49-7) → dimethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (3014-58-2,5826-73-3,7184-07-8,39589-98-5,116404-47-8,117604-28-1,135357-64-1)

Guidance literature:

With hydroquinone; at 150 ℃; for 2h; Microwave irradiation;

DOI:10.1039/c5ob00621j

Reference yield: 94.0%

methanol (67-56-1) + 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6) → dimethyl 5-cis-norbornene-2,3-dicarboxylate (3014-58-2,5826-73-3,7184-07-8,39589-98-5,116404-47-8,117604-28-1,135357-64-1)

Guidance literature:

With hydrogenchloride; In water; at 65 ℃; for 4h; Inert atmosphere;

upstream raw materials:

cyclopenta-1,3-diene

dimethylfumarate

dimethyl cis-but-2-ene-1,4-dioate

methanol

Downstream raw materials:

5c-oxo-(4at,10bt)-1,2,3,4,4a,5,6,10b-octahydro-5λ⁴-1r,4c-methano-dibenzo[c,e][1,2]thiazine-2r',3t'-dicarboxylic acid dimethyl ester

exo-2,3-dicarbomethoxy-exo-5-(dimethylchlorosilyl)bicyclo<2.2.1>heptane

trans-2,3-dicarbomethoxy-exo-5-(dimethylchlorosilyl)bicyclo<2.2.1>heptane

γ-lactone of exo-5-phenylthio-endo-6-hydroxy-endo-3-methoxycarbonylbicyclo<2.2.1>heptane-endo-2-carboxylic acid

Refernces

• 1、 Boobalan, Ramalingam,Chein, Rong-Jie. "Oxathiaborolium-Catalyzed Enantioselective [4 + 2] Cycloaddition and Its Application in Lewis Acid Coordinated and Chiral Lewis Acid Catalyzed [4 + 2] Cycloaddition". . p. 6760 - 6764. Retrieved 2021/09/11.
• 2、 Chang, Alice B.,Lin, Tzu-Pin,Thompson, Niklas B.,Luo, Shao-Xiong,Liberman-Martin, Allegra L.,Chen, Hsiang-Yun,Lee, Byeongdu,Grubbs, Robert H.. "Design, Synthesis, and Self-Assembly of Polymers with Tailored Graft Distributions". supporting information. p. 17683 - 17693. Retrieved 2017/12/15.