2-Aminoadamantane-2-carboxylic acid

Base Information

• Chemical Name: 2-Aminoadamantane-2-carboxylic acid
• CAS No.: 42381-05-5
• Molecular Formula: C11H17NO2
• Molecular Weight: 195.261
• Hs Code.: 2922499990
• NSC Number: 145160
• UNII: F52G3FRR68
• DSSTox Substance ID: DTXSID00195187
• Nikkaji Number: J3.383.109I
• Mol file: 42381-05-5.mol

Synonyms:adamantanine;adamantanine hydrochloride

Chemical Property of 2-Aminoadamantane-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.03E-05mmHg at 25°C
• Refractive Index: 1.57
• Boiling Point: 346.2 °C at 760 mmHg
• PKA: 2.49±0.20(Predicted)
• Flash Point: 163.2 °C
• PSA: 63.32000
• Density: 1.238 g/cm³
• LogP: 1.92490
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 195.125928785
• Heavy Atom Count: 14
• Complexity: 259

Purity/Quality:

98%,99%, ^*data from raw suppliers

Adamantanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

Useful:

• Canonical SMILES: C1C2CC3CC1CC(C2)C3(C(=O)O)N
• Uses: Adamantanine is a γ-turn inducer for peptides. A potential cholecystokinin-B (CCK-B) receptor selective ligands. Also, it inhibits the transport of L-leucine and L-methionine into Ehrlich ascites cells.

Technology Process of 2-Aminoadamantane-2-carboxylic acid

There total 3 articles about 2-Aminoadamantane-2-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:

spiro[adamantane-2,4'-imidazolidine]-2',5'-dione (50346-47-9) → 2-amino-2-adamantanecarboxylic acid (42381-05-5)

Guidance literature:

With sodium hydroxide; at 195 ℃; for 2h; under 12929 Torr;

DOI:10.1016/j.bmc.2013.04.075

Reference yield:

2-Adamantanone (700-58-3) → 2-amino-2-adamantanecarboxylic acid (42381-05-5)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium carbonate / ethanol; water / 2 h / 20 - 150 °C / Inert atmosphere; Microwave irradiation

2: sodium hydroxide / 2 h / 195 °C / 12929 Torr

With ammonium carbonate; sodium hydroxide; In ethanol; water;

DOI:10.1016/j.bmc.2013.04.075

Reference yield:

→ 2-amino-2-adamantanecarboxylic acid (42381-05-5)

Guidance literature:

DOI:10.1021/jm00265a016

upstream raw materials:

2-Adamantanone

spiro[adamantane-2,4'-imidazolidine]-2',5'-dione

Downstream raw materials:

2-N-benzyloxycarbonylamino-2-hydroxycarbonyl-adamantane

2-amino-adamantane-2-carboxylic acid tert-butyl ester

2-N-benzyloxycarbonylamino-2-tert-butyloxycarbonyl-adamantane

N-[(2-tert-butyloxycarbonyl)-2-adamantyl] [(2S)-2-amino-3-(4-tert-butyloxyphenyl)]propanamide

Refernces

• 1、 Baxendale,Cheung,Kitching,Ley,Shearman. "The synthesis of neurotensin antagonist SR 48692 for prostate cancer research". . p. 4378 - 4387. Retrieved 2013/07/27.