Methyl bicyclo[2.2.2]oct-5-ene-2-carboxylate

Base Information

• Chemical Name: Methyl bicyclo[2.2.2]oct-5-ene-2-carboxylate
• CAS No.: 771-73-3
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• NSC Number: 167503
• DSSTox Substance ID: DTXSID90304827
• Nikkaji Number: J1.520.744B
• Mol file: 771-73-3.mol

Synonyms:771-73-3;NSC167503;SCHEMBL11801332;DTXSID90304827;NSC-167503;methyl bicyclo[2.2.2]oct-5-ene-2-carboxylate

Chemical Property of Methyl bicyclo[2.2.2]oct-5-ene-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.126mmHg at 25°C
• Boiling Point: 218.4°Cat760mmHg
• Flash Point: 76.7°C
• Density: 1.08g/cm³
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 166.099379685
• Heavy Atom Count: 12
• Complexity: 220

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC2CCC1C=C2

Technology Process of Methyl bicyclo[2.2.2]oct-5-ene-2-carboxylate

There total 23 articles about Methyl bicyclo[2.2.2]oct-5-ene-2-carboxylate 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: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + bicyclo<2.2.2>oct-5-ene-2-exo-carboxylic acid (20507-56-6,20507-57-7,40335-74-8,40610-12-6,41977-03-1,41977-04-2) → 5-exo-methoxycarbonylbicyclo<2.2.2>oct-2-ene (771-73-3,25578-17-0,25694-29-5,54515-88-7,68069-55-6)

Guidance literature:

In diethyl ether;

DOI:10.1248/cpb.44.296

Reference yield: 99.0%

cyclohexa-1,3-diene (1165952-91-9) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl endo-bicyclo<2.2.2>oct-5-ene-2-carboxylate (771-73-3,25578-17-0,25694-29-5,54515-88-7,68069-55-6)

Guidance literature:

With trimethylsilyl bis(trifluoromethanesulfonyl)imide; In toluene; at 0 ℃; for 3.5h; Inert atmosphere;

DOI:10.1021/jo502618g

Reference yield: 99.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + cyclohexene (110-83-8) → methyl endo-bicyclo<2.2.2>oct-5-ene-2-carboxylate (771-73-3,25578-17-0,25694-29-5,54515-88-7,68069-55-6)

Guidance literature:

With trimethylsilyl bis(trifluoromethanesulfonyl)imide; In toluene; at 0 - 20 ℃; for 1h;

DOI:10.1039/c3ob42152j

upstream raw materials:

cyclohexa-1,3-diene

acrylic acid methyl ester

methanol

2-methoxycarbonylbicyclo<2.2.2>octa-2,5-diene

Downstream raw materials:

bicyclo<2.2.2>oct-5-ene-2-exo-carboxylic acid

5-exo-methoxycarbonylbicyclo<2.2.2>oct-2-ene

exo-5-phenylthiobicyclo<2.2.2>octane-2,6-carbolactone