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

Base Information

• Chemical Name: Diethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
• CAS No.: 26272-67-3
• Molecular Formula: C₁₃H₁₈O₄
• Molecular Weight: 238.284
• NSC Number: 69976
• DSSTox Substance ID: DTXSID10290617
• Nikkaji Number: J1.353.959F
• Mol file: 26272-67-3.mol

Synonyms:Diethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate;26272-67-3;bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid diethyl ester;NSC69976;SCHEMBL1451358;DTXSID10290617;UXRMRBNLTQHPEU-UHFFFAOYSA-N;NSC-69976;Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylicacid, 2,3-diethyl ester, (1S,2S,3S,4R)-rel-;Diethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate #;Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid, diethyl ester;Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylicacid,2,3-diethyl ester,(1S,2S,3S,4R)-rel-

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

Chemical Property:

• Vapor Pressure: 0.000395mmHg at 25°C
• Boiling Point: 317°Cat760mmHg
• Flash Point: 152.3°C
• PSA: 52.60000
• Density: 1.152g/cm³
• LogP: 1.55090
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 238.12050905
• Heavy Atom Count: 17
• Complexity: 315

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1C2CC(C1C(=O)OCC)C=C2

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

There total 5 articles about Diethyl 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: 98.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + diethyl Fumarate (623-91-6) → diethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (5883-33-0,7184-08-9,7288-32-6,26272-67-3,133442-01-0)

Guidance literature:

In water; at 25 ℃; Solvent; Kinetics;

DOI:10.1021/jo500733v

Reference yield: 82.0%

bi(cyclopentadiene) (77-73-6,933-60-8,1755-01-7,25038-78-2) + diethyl Fumarate (623-91-6) → diethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (5883-33-0,7184-08-9,7288-32-6,26272-67-3,133442-01-0)

Guidance literature:

With hydroquinone; at 150 ℃; for 1h; Microwave irradiation;

DOI:10.1055/s-0031-1289610

Reference yield:

diethyl (endo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (7288-32-6) → diethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (5883-33-0,7184-08-9,7288-32-6,26272-67-3,133442-01-0)

Guidance literature:

With sodium ethanolate; In ethanol; Heating;

DOI:10.1002/(SICI)1096-9888(199609)31:9<1028::AID-JMS388>3.0.CO;2-K

upstream raw materials:

cyclopenta-1,3-diene

diethyl Fumarate

diethyl (endo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Downstream raw materials:

(+/-)-(2-endo,3-exo)-bicyclo[2.2.1]hept-5-eno-2,3-dimethanol

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