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

Base Information

• Chemical Name: 4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid
• CAS No.: 18720-35-9
• Molecular Formula: C11H16O4
• Molecular Weight: 212.246
• Hs Code.: 2918990090
• European Community (EC) Number: 814-024-1
• DSSTox Substance ID: DTXSID60453033
• Nikkaji Number: J1.846.913H
• Wikidata: Q72489433
• Mol file: 18720-35-9.mol

Synonyms:4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid;18720-35-9;4-methoxycarbonylbicyclo[2.2.2]octane-1-carboxylic acid;BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID MONOMETHYL ESTER;MFCD18459359;4-(methoxycarbonyl)bicyclo-[2.2.2]octane-1-carboxylic acid;SCHEMBL646389;AMY711;DTXSID60453033;BCP08380;AKOS005145885;AKOS015920349;CS-W001270;GS-3863;MB06047;AC-25478;SY024675;A4142;FT-0649016;M2855;EN300-109770;A1-01463;J-012047;Methyl hydrogen bicyclo[2,2,2]octane-1,4-dicarboxylate;Methyl hydrogen bicyclo[2.2.2]octane-1,4-dicarboxylate;Z1427941563;4-(Methoxycarbonyl)bicyclo[2.2.2]octan-1-carboxylic Acid;4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylicacid;Bicyclo[2.2.2]octane-1,4-dicarboxylic acid 4-methyl ester;Monomethyl Hydrogen Bicyclo[2.2.2]octane-1,4-dicarboxylate;4-(methoxycarbonyl) bicyclo[2.2.2]octane-1-carboxylic acid;Bicyclo-[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester;4-(METHOXYCARBONYL)BICYCLO[2.2.2]OCTANE-1-CARBOXYLIC ACI;BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER;4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid, AldrichCPR

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 186.0 to 190.0 °C
• Refractive Index: 1.551
• Boiling Point: 322.473 °C at 760 mmHg
• PKA: 4.77±0.10(Predicted)
• Flash Point: 122.436 °C
• PSA: 63.60000
• Density: 1.307 g/cm³
• LogP: 1.58460
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 212.10485899
• Heavy Atom Count: 15
• Complexity: 283

Purity/Quality:

99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36
• Safety Statements: 26-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C12CCC(CC1)(CC2)C(=O)O
• Uses: 4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic Acid has been used as a reactant for the preparation of bicyclo-octyltriazole inhibitors of HSD1 for metabolic syndrome treatment.

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

There total 16 articles about 4-(Methoxycarbonyl)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: 95.0%

dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate (1459-96-7) → bicyclo[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (18720-35-9)

Guidance literature:

With potassium hydroxide; In methanol; water; at 90 ℃;

DOI:10.1016/j.bmcl.2014.10.057

Reference yield:

dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate (1459-96-7) → 1,4-bicyclo[2.2.2]octanedicarboxylic acid (711-02-4) + bicyclo[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (18720-35-9)

Guidance literature:

With barium dihydroxide; In methanol; water; for 18h; Ambient temperature;

Reference yield:

dimethyl 1,4-cyclohexane dicarboxylate (94-60-0) → bicyclo[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (18720-35-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / LDA, HMPA / tetrahydrofuran / -78 deg C to RT

2: 50 percent / KOH / methanol; H₂O / 24 h / 50 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; water;

DOI:10.1016/S0040-4039(98)02411-3

upstream raw materials:

dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate

methyl 4-phenylbicyclo<2.2.2>octane-1-carboxylate

dimethyl 1,4-cyclohexane dicarboxylate

dimethyl 1,4-dioxobicyclo<2.2.2>octane-2,5-dicarboxylate

Downstream raw materials:

4-hydroxymethyl-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester

methyl 4-(((benzyloxy)carbonyl)amino)bicyclo[2.2.2]octane-1-carboxylate

methyl 4-phenylbicyclo<2.2.2>octane-1-carboxylate

methyl 4-(4-nitrophenyl)bicyclo[2.2.2]octane-1-carboxylate

Refernces

• 1、 -. "POLYMERIZABLE COMPOUND AND OPTICAL ANISOTROPIC BODY". Paragraph 0202-0204. . Retrieved 2018/01/02.
• 2、 Bandak, Dmytro,Babii, Oleg,Vasiuta, Roman,Komarov, Igor V.,Mykhailiuk, Pavel K.. "Design and synthesis of novel 19F-amino acid: A promising 19F NMR label for peptide studies". supporting information. p. 226 - 229. Retrieved 2015/03/05.