Dimethyl 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

Base Information

• Chemical Name: Dimethyl 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
• CAS No.: 1829-60-3
• Molecular Formula: C10H10O5
• Molecular Weight: 210.186
• Mol file: 1829-60-3.mol

Synonyms:dimethyl oxanorbornadiene-2,3-dicarboxylate;dimethyl 7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate;2,3-bis(methoxycarbonyl)-7-oxabicyclo{2.2.1}hepta-2,5-diene;7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester;7-Oxa-norborna-2,5-dien-2,3-dicarbonsaeure-dimethylester;dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate;

Chemical Property of Dimethyl 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

Chemical Property:

• Refractive Index: 1.4940 to 1.4980
• Boiling Point: 120°C/0.5mmHg(lit.)
• PSA: 61.83000
• LogP: -0.03380

Purity/Quality:

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

Dimethyl 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Dimethyl 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

There total 7 articles about Dimethyl 7-Oxabicyclo[2.2.1]hepta-2,5-diene-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: 92.0%

furan (110-00-9) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate (1829-60-3)

Guidance literature:

In dichloromethane; at -15 - 20 ℃; for 24h;

DOI:10.1021/jo301909j

Reference yield: 85.0%

furan (110-00-9) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate (1829-60-3)

Guidance literature:

Heating;

DOI:10.1007/s00044-015-1324-x

Reference yield:

furan (110-00-9) + dimethyl acetylenedicarboxylate (762-42-5) → 1,4,5,8-tetrahydro-1t,4t;5t,8t-diepoxido-naphthalene-4ar,8ac-dicarboxylic acid dimethyl ester (10152-89-3,25860-27-9) + anti-methyl 11,12-dioxatetracyclo[6.2.1.13,6.02,7.]dodeca-4.9-diene-2,7-dicarboxylate (25860-27-9) + dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate (1829-60-3)

Guidance literature:

With Zn(II)-exchanged K₁₀ montmorillonite; at 25 ℃; for 96h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(98)02091-7

upstream raw materials:

furan

dimethyl acetylenedicarboxylate

1,4-Dioxocin

2,5-dimethylfuran

Downstream raw materials:

furan

3-phenylisoxazole

dimethyl 3,4-furandicarboxylate

dimethyl 3-phenylisoxazole-4,5-dicarboxylate

Refernces

• 1、 Yilmaz, ?zgür,?im?ek Ku?, Nermin,Küce, Pinar,Coral, G?khan,?elik, Ayla,Gültekin, Mehmet Serdar. "Simple and convenient preparation of some bicyclic alcohols and epoxide derivatives: Promising antibiotic activities of (rac)-dimethyl 3,8-dioxatricyclo[3.2.1.02,4]oct-6-ene-6,7-dicarboxylate". . p. 2709 - 2716. Retrieved 2015.
• 2、 Lv, Weiwei,Wen, Si,Yu, Jia,Cheng, Guolin. "Palladium-Catalyzed Ortho-Silylation of Aryl Iodides with Concomitant Arylsilylation of Oxanorbornadiene: Accessing Functionalized (Z)-β-Substituted Vinylsilanes and Their Analogues". . p. 4984 - 4987. Retrieved 2018.
• 3、 Murai, Masahito,Ogita, Takuya,Takai, Kazuhiko. "Regioselective arene homologation through rhenium-catalyzed deoxygenative aromatization of 7-oxabicyclo[2.2.1]hepta-2,5-dienes". . p. 2332 - 2335. Retrieved 2019/02/27.