5-(Methoxycarbonyl)bicyclo[3.2.1]octane-1-carboxylic acid

Base Information

• Chemical Name: 5-(Methoxycarbonyl)bicyclo[3.2.1]octane-1-carboxylic acid
• CAS No.: 110371-27-2
• Molecular Formula: C11H16O4
• Molecular Weight: 212.246
• Hs Code.: 2918990090
• European Community (EC) Number: 875-323-0
• DSSTox Substance ID: DTXSID10548706
• Mol file: 110371-27-2.mol

Synonyms:110371-27-2;5-(Methoxycarbonyl)bicyclo[3.2.1]octane-1-carboxylic acid;bicyclo[3.2.1]octane-1,5-dicarboxylic acid monomethyl ester;5-methoxycarbonylbicyclo[3.2.1]octane-1-carboxylic acid;Oprea1_045954;SCHEMBL1567508;5-(Methoxycarbonyl)bicyclo[3.2.1]octane-1-carboxylicacid;DTXSID10548706;AS-82347;CS-0217942;E77449;EN300-9428677

Chemical Property of 5-(Methoxycarbonyl)bicyclo[3.2.1]octane-1-carboxylic acid

Chemical Property:

• Melting Point: 78-80 °C
• Boiling Point: 322.5±25.0 °C(Predicted)
• PKA: 4.48±0.40(Predicted)
• PSA: 63.60000
• Density: 1.307±0.06 g/cm3(Predicted)
• LogP: 1.58460
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 212.10485899
• Heavy Atom Count: 15
• Complexity: 312

Purity/Quality:

99%, ^*data from raw suppliers

5-(Methoxycarbonyl)bicyclo[3.2.1]octane-1-carboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C12CCCC(C1)(CC2)C(=O)O

Technology Process of 5-(Methoxycarbonyl)bicyclo[3.2.1]octane-1-carboxylic acid

There total 5 articles about 5-(Methoxycarbonyl)bicyclo[3.2.1]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: 67.0%

dimethyl bicyclo<3.2.1>octane-1,5-dicarboxylate (106004-11-9) → bicyclo[3.2.1]octane-1,5-dicarboxylic acid monomethyl ester (110371-27-2)

Guidance literature:

dimethyl bicyclo<3.2.1>octane-1,5-dicarboxylate; With barium hydroxide octahydrate; water; In ethanol; Inert atmosphere; Reflux;

With hydrogenchloride; In water; at 18 - 25 ℃; pH=1 - 2;

Reference yield:

dimethyl bicyclo<3.2.1>octane-1,5-dicarboxylate (106004-11-9) → bicyclo[3.2.1]octane-1,5-dicarboxylic acid monomethyl ester (110371-27-2) + bicyclo[3.2.1]octane-1,5-dicarboxylic acid

Guidance literature:

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

Reference yield:

dimethyl cyclohexane-1,3-dicarboxylate (62638-06-6) → bicyclo[3.2.1]octane-1,5-dicarboxylic acid monomethyl ester (110371-27-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisopropylamine; n-butyllithium / hexane; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 25 °C

2.1: diisopropylamine; n-butyllithium / hexane; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrahydrofuran / -78 - 25 °C / Inert atmosphere

3.1: water; barium hydroxide octahydrate / ethanol / Inert atmosphere; Reflux

3.2: 18 - 25 °C / pH 1 - 2

With n-butyllithium; barium hydroxide octahydrate; water; diisopropylamine; In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ethanol; hexane;

upstream raw materials:

dimethyl bicyclo<3.2.1>octane-1,5-dicarboxylate

dimethyl cyclohexane-1,3-dicarboxylate

cyclohexane-1,3-dicarboxylic acid

dimethyl 1-(2'-chloroethyl)cyclohexane-1,3-dicarboxylate

Downstream raw materials:

methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate

5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylic acid

benzyl 5-aminobicyclo[3.2.1]octan-1-ylcarbamate

benzyl (5-(3-fluorobcnzamido)bicyclo[3.2.1]octan-1-yl)carbamate