4-(Ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid

Base Information

• Chemical Name: 4-(Ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid
• CAS No.: 834-50-4
• Molecular Formula: C12H18O4
• Molecular Weight: 226.273
• Hs Code.: 2918990090
• NSC Number: 177416
• DSSTox Substance ID: DTXSID10306540
• Wikidata: Q82053683
• Mol file: 834-50-4.mol

Synonyms:4-(Ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid;834-50-4;4-ethoxycarbonylbicyclo[2.2.2]octane-1-carboxylic acid;NSC177416;4-(Ethoxycarbonyl)bicyclo-[2.2.2]octane-1-carboxylic acid;Enamine_002030;Oprea1_007716;SCHEMBL1566652;1-ethoxycarbonylbicyclo[2.2.2]octane-4-carboxylic acid;DTXSID10306540;AKCJDZLLWVXNFU-UHFFFAOYSA-N;HMS1399M06;AKOS001025445;NSC-177416;NCGC00321751-01;CS-0092269;FT-0705713;D75333;AB01317723-02;EN300-1191719;Z56755887;4-(Ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylicacid;bicyclo[2.2.2]octane-1,4-dicarboxylic acid monoethyl ester

Chemical Property of 4-(Ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid

Chemical Property:

• Vapor Pressure: 2.06E-05mmHg at 25°C
• Refractive Index: 1.543
• Boiling Point: 336.8 °C at 760 mmHg
• Flash Point: 125.2 °C
• PSA: 63.60000
• Density: 1.265g/cm³
• LogP: 1.97470
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 226.12050905
• Heavy Atom Count: 16
• Complexity: 297

Purity/Quality:

99%, ^*data from raw suppliers

4-(Ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C12CCC(CC1)(CC2)C(=O)O

Technology Process of 4-(Ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid

There total 5 articles about 4-(Ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid 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: 62.0%

Bicyclo<2.2.2.>octan-1,4-dicarbonsauere-ethylester (1659-75-2) → 4-(ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid (834-50-4)

Guidance literature:

With potassium hydroxide; In ethanol; Reflux;

DOI:10.1021/jm1009956

Reference yield:

(+/-)-dispiro[[1,3]dithiane-2,2'-bicyclo[2.2.2]octane-5',2''-[1,3]dithiane]-1',4'-dicarboxylic acid diethyl ester (41034-55-3) → 4-(ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid (834-50-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Raney nickel; ethanol

2: ethanolic KOH

With potassium hydroxide; ethanol; nickel;

DOI:10.3758/BF03211828

Reference yield:

diethyl 1,4-cyclohexanedione-2,5-dicarboxylate (787-07-5) → 4-(ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid (834-50-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / 1,2-dimethoxyethane; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: Inert atmosphere; Heating

2.1: hydrogenchloride / chloroform / 7 h / 0 °C / Inert atmosphere

3.1: Raney nickel (Ra-Ni) / ethanol / 4 h / Inert atmosphere; Reflux

4.1: potassium hydroxide / ethanol / Reflux

With hydrogenchloride; sodium hydride; potassium hydroxide; In 1,2-dimethoxyethane; ethanol; chloroform; mineral oil;

DOI:10.1021/jm1009956

upstream raw materials:

Bicyclo<2.2.2.>octan-1,4-dicarbonsauere-ethylester

(+/-)-dispiro[[1,3]dithiane-2,2'-bicyclo[2.2.2]octane-5',2''-[1,3]dithiane]-1',4'-dicarboxylic acid diethyl ester

diethyl 1,4-cyclohexanedione-2,5-dicarboxylate

2,5-Bis-ethylendimercapto-bicyclo<2,2,2>octan-1,4-dicarbonsaeure-diethylester

Downstream raw materials:

ethyl 4-iodobicyclo[2.2.2]octane-1-carboxylate

4-iodo-N-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-N-(pyridin-2-yl)bicyclo[ 2.2.2]octane-1-carboxamide

4-iodo-N-(2-(4-(2-hydroxyphenyl)piperazin-1-yl)ethyl)-N-(pyridin-2-yl)bicyclo[ 2.2.2]octane-1-carboxamide

4-iodobicyclo<2.2.2>octane-1-carboxylic acid

Refernces