Ethyl bicyclo[2.2.1]heptane-2-carboxylate

Base Information

• Chemical Name: Ethyl bicyclo[2.2.1]heptane-2-carboxylate
• CAS No.: 61242-71-5
• Molecular Formula: C10H16O2
• Molecular Weight: 168.236
• DSSTox Substance ID: DTXSID00976751
• Mol file: 61242-71-5.mol

Synonyms:ethyl bicyclo[2.2.1]heptane-2-carboxylate;SCHEMBL1862636;DTXSID00976751;CIHQTYMOCREEQU-UHFFFAOYSA-N;AKOS009165455;bicyclo[2.2.1]heptane-2-carboxylic acid, ethyl ester

Chemical Property of Ethyl bicyclo[2.2.1]heptane-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.129mmHg at 25°C
• Refractive Index: 1.4890 (estimate)
• Boiling Point: 218°C at 760 mmHg
• Flash Point: 80.7°C
• PSA: 26.30000
• Density: 1.055g/cm³
• LogP: 1.98570
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 188

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CC2CCC1C2

Technology Process of Ethyl bicyclo[2.2.1]heptane-2-carboxylate

There total 5 articles about Ethyl bicyclo[2.2.1]heptane-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:

bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid ethyl ester (51789-95-8) → (1R,2S,4S)-Bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (61242-71-5)

Guidance literature:

With 10 wt% Pd(OH)2 on carbon; hydrogen; In methanol; for 6h; under 75007.5 Torr;

DOI:10.1016/j.bmc.2014.04.004

Reference yield:

Diethyl Bicyclo<2.2.1>hept-5-ene-2,2-dicarboxylate (65132-76-5) → (1R,2S,4S)-Bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (61242-71-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90.9 percent / Hydrogen / 10percent Pd/C / ethyl acetate

2: LiCl, H₂O / dimethylsulfoxide / 4 h / 185 °C

With water; hydrogen; lithium chloride; palladium on activated charcoal; In dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/jo01309a007

Reference yield:

Diethyl Bicyclo<2.2.1>heptane-2,2-dicarboxylate (30934-87-3) → (1R,2S,4S)-Bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (61242-71-5) + Aethyl-norbornan-exo-2-carboxylat (4755-79-7)

Guidance literature:

With water; lithium chloride; In dimethyl sulfoxide; at 185 ℃; for 4h; Yield given. Yields of byproduct given;

DOI:10.1021/jo01309a007

upstream raw materials:

Diethyl Bicyclo<2.2.1>heptane-2,2-dicarboxylate

Diethyl Bicyclo<2.2.1>hept-5-ene-2,2-dicarboxylate

bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid ethyl ester

endo-Dicyclopentadien

Downstream raw materials:

exo-2-bromobicyclo<2.2.1>heptane-1-carboxylic acid

Refernces

• 1、 Krapcho, A. Paul,Weimaster, John F.. "Stereochemistry of Decarbalkoxylation of Cyclic Geminal Diesters Effected by Water and Lithium Chloride in Me2SO". . p. 4105 - 4111. Retrieved 2007/10/02.