7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, methyl ester

Base Information

• Chemical Name: 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, methyl ester
• CAS No.: 21987-33-7
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• European Community (EC) Number: 832-706-7
• DSSTox Substance ID: DTXSID50483460
• Nikkaji Number: J1.843.069J
• Mol file: 21987-33-7.mol

Synonyms:21987-33-7;methyl 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate;7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, methyl ester;methyl 7-oxa-5-norbornen-2-carboxylate;starbld0027456;methyl endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate;SCHEMBL2960975;DTXSID50483460;OZONFNLDQRXRGI-UHFFFAOYSA-N;17791-33-2;MFCD24499834;204988-60-3;AS-79140;SY344230;D79375;EN300-217223;2-carbomethoxy-7-oxabicyclo(2,2,1)hept-5-ene;2-carbomethoxy-7-oxabicyclo(2.2.1)hept-5-ene;rac-methyl 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate;7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylicacid,methylester,endo-(+)-(9ci)

Chemical Property of 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, methyl ester

Chemical Property:

• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 209

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1CC2C=CC1O2

Technology Process of 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, methyl ester

There total 10 articles about 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, methyl 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: 96.0%

methanol (67-56-1) + (+/-)-7-oxabicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (24363-23-3,38263-45-5,38263-46-6,64589-22-6,90760-55-7,90760-56-8,117772-64-2) → exo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (17791-32-1,17791-33-2,21987-33-7,88517-51-5,88517-52-6,204988-60-3)

Guidance literature:

With acetyl chloride; for 3h; Ambient temperature;

DOI:10.1016/0008-6215(88)85054-7

Reference yield: 60.0%

furan (110-00-9) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid,methyl ester (21987-33-7,204988-60-3)

Guidance literature:

DOI:10.1021/ja00311a053

Reference yield: 40.0%

furan (110-00-9) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid methyl ester (88517-51-5,204988-60-3) + exo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (17791-32-1,17791-33-2,21987-33-7,88517-51-5,88517-52-6,204988-60-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/j.tetlet.2018.04.031

upstream raw materials:

furan

acrylic acid methyl ester

acryloyl chloride

methanol

Downstream raw materials:

rac-methyl 5-hydroxycyclohexa-1,3-diene-1-carboxylate

exo-2,3-epoxy-6-methoxycarbonyl-7-oxabicyclo<2.2.1>heptane

(+/-)-methyl-5-β-O-t-butyldimethylsilyloxycyclohexa-1,3-dienoate

methyl (+/-)-exo-3,8-dioxatricylo<3.2.1.0^2,4>oktane-6exo-carboxylate