Methyl bicyclo(2.2.1)hepta-2,5-dienecarboxylate

Base Information

• Chemical Name: Methyl bicyclo(2.2.1)hepta-2,5-dienecarboxylate
• CAS No.: 3604-36-2
• Molecular Formula: C9H10 O2
• Molecular Weight: 150.177
• Hs Code.: 2916209090
• DSSTox Substance ID: DTXSID40957443
• Nikkaji Number: J405.065G
• Mol file: 3604-36-2.mol

Synonyms:3604-36-2;Bicyclo[2.2.1]hepta-2,5-diene-2-carboxylicacid, methyl ester;Methyl bicyclo(2.2.1)hepta-2,5-dienecarboxylate;Methyl bicyclo[2.2.1]hepta-2,5-diene carboxylate;SCHEMBL4169291;DTXSID40957443;2-methyloxycarbonyl-bicyclo[2.2.1]hepta-2,5-diene;methyl bicyclo[2.2.1]hepta-2,5-diene-2-carboxylate;Methylester of Bicyclo[2.2.1]hepta-2,5-dien-2-carboxylic acid;Bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid, methyl ester, (1S,4R)-

Chemical Property of Methyl bicyclo(2.2.1)hepta-2,5-dienecarboxylate

Chemical Property:

• Vapor Pressure: 0.178mmHg at 25°C
• Boiling Point: 212°Cat760mmHg
• Flash Point: 77.8°C
• PSA: 26.30000
• Density: 1.178g/cm³
• LogP: 1.29170
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 150.068079557
• Heavy Atom Count: 11
• Complexity: 250

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=CC2CC1C=C2

Technology Process of Methyl bicyclo(2.2.1)hepta-2,5-dienecarboxylate

There total 7 articles about Methyl bicyclo(2.2.1)hepta-2,5-dienecarboxylate 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: 82.3%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + propynoic acid methyl ester (922-67-8) → methyl bicyclo[2.2.1]hepta-2,5-diene-2-carboxylate (3604-36-2)

Guidance literature:

With aluminium trichloride; In benzene; for 1.5h; cooling;

DOI:10.1039/b100751n

Reference yield: 78.0%

Tetracyclo<3.2.0.02,7.04,6>heptan-1-carbonsaeure-methylester (24161-47-5,327035-53-0,327035-52-9) → methyl bicyclo[2.2.1]hepta-2,5-diene-2-carboxylate (3604-36-2)

Guidance literature:

di-μ-chlorobis(norbornadiene)dirhodium(I); at 0 ℃; for 6h;

Reference yield: 74.0%

(1S,2S,3R,4R)-3-Chloro-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester → methyl bicyclo[2.2.1]hepta-2,5-diene-2-carboxylate (3604-36-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 25 ℃; for 3h;

DOI:10.1021/ja991190k

upstream raw materials:

cyclopenta-1,3-diene

propynoic acid methyl ester

Tetracyclo<3.2.0.0^2,7.0^4,6>heptan-1-carbonsaeure-methylester

3-((1S,2S,3R,4R)-3-Chloro-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one

Downstream raw materials:

2-phenylnorborn-2-ene

Refernces

• 1、 Fienemann,Hoffmann. "". . p. 2802. Retrieved 1979.
• 2、 Nishino,Nakamura,Inoue. "Synchronous enantiomeric enrichment of both reactant and product by absolute asymmetric synthesis using circularly polarized light. Part 1. Theoretical and experimental verification of the asymmetric photoisomerization of methyl norbornadiene-2-carboxylate to methyl quadricyclane-1-carboxylate". . p. 1693 - 1700. Retrieved 2007/10/03.