Methyl bicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

Base Information

• Chemical Name: Methyl bicyclo[2.2.1]hepta-2,5-diene-7-carboxylate
• CAS No.: 5597-69-3
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.177
• DSSTox Substance ID: DTXSID90505493
• Wikidata: Q82360680
• Mol file: 5597-69-3.mol

Synonyms:5597-69-3;Methyl bicyclo[2.2.1]hepta-2,5-diene-7-carboxylate;DTXSID90505493

Chemical Property of Methyl bicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

Chemical Property:

• PSA: 26.30000
• LogP: 1.14760
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 150.068079557
• Heavy Atom Count: 11
• Complexity: 210

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1C2C=CC1C=C2

Technology Process of Methyl bicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

There total 3 articles about Methyl bicyclo[2.2.1]hepta-2,5-diene-7-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: 97.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + bicyclo<2.2.1>hepta-2,5-diene-7-carboxylic acid (5597-66-0) → 7-methoxycarbonylbicyclo<2.2.1>hepta-2,5-diene (5597-69-3)

Guidance literature:

In diethyl ether; at 0 - 100 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)97733-6

Reference yield:

7-chlorobicyclo<2.2.1>hepta-2,5-diene (1609-39-8) → 7-methoxycarbonylbicyclo<2.2.1>hepta-2,5-diene (5597-69-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium p,p'-di-t-butylbipenyl; 2.) NaOH, HCl / 1.) -78 deg C, 5 min; 2.) room temp

2: 97 percent / diethyl ether / 0.5 h / 0 - 100 °C

With hydrogenchloride; sodium hydroxide; lithium 4,4′-di(tert-butyl)biphenyl; In diethyl ether;

DOI:10.1016/S0040-4020(01)97733-6

Reference yield:

→ 7-Carbomethoxynorbornadien (5597-69-3)

Guidance literature:

7-Cyanonorbornadien, KOH;

DOI:10.1016/S0040-4039(01)99697-2

upstream raw materials:

diazomethane

bicyclo<2.2.1>hepta-2,5-diene-7-carboxylic acid

7-chlorobicyclo<2.2.1>hepta-2,5-diene

Downstream raw materials:

C₁₇H₁₇⁽²⁾HN₂O₄S

C₁₆H₁₈N₂O₂S

Refernces

• 1、 Klumpp,Bickelhaupt. "". . p. 865,866. Retrieved 1966.