(1S,2S)-2-Aminocyclohexanecarboxylic Acid

Base Information

• Chemical Name: (1S,2S)-2-Aminocyclohexanecarboxylic Acid
• CAS No.: 24716-93-6
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.186
• Hs Code.: 2922390090
• European Community (EC) Number: 688-972-8
• DSSTox Substance ID: DTXSID90427828
• Nikkaji Number: J593.002B
• Wikidata: Q82240537
• Mol file: 24716-93-6.mol

Synonyms:(1S,2S)-2-Aminocyclohexanecarboxylic Acid;24716-93-6;(1S,2S)-2-aminocyclohexane-1-carboxylic acid;Cyclohexanecarboxylic acid, 2-amino-, (1S,2S)-;(1S,2S)-2-AminocyclohexanecarboxylicAcid;SCHEMBL48334;DTXSID90427828;USQHEVWOPJDAAX-WDSKDSINSA-N;MFCD01318270;AKOS006340938;AKOS015854132;AS-30258;(1S,2S)-2-amino-cyclohexanecarboxylic acid;2beta-Amino-1alpha-cyclohexanecarboxylic acid;CS-0139609;Cyclohexanecarboxylic acid,2-amino-,(1S,2S)-;EN300-1168694;A877817;(1~{S},2~{S})-2-azanylcyclohexane-1-carboxylic acid;(1S,2S)-2-aminocyclohexanecarboxylic acid, AldrichCPR

Chemical Property of (1S,2S)-2-Aminocyclohexanecarboxylic Acid

Chemical Property:

• Vapor Pressure: 0.00103mmHg at 25°C
• Melting Point: 0 °C
• Refractive Index: 76.5 ° (C=1, H2O)
• Boiling Point: 280 °C at 760 mmHg
• PKA: 3.77±0.28(Predicted)
• Flash Point: 123.1 °C
• PSA: 63.32000
• Density: 1.133 g/cm³
• LogP: 1.28880
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility.: Soluble in water.
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 143.094628657
• Heavy Atom Count: 10
• Complexity: 136

Purity/Quality:

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

(1S,2S)-2-Aminocyclohexanecarboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)C(=O)O)N
• Isomeric SMILES: C1CC[C@@H]([C@H](C1)C(=O)O)N
• Uses: (1S,2S)-2-Aminocyclohexanecarboxylic acid is used in the preparation of enantiomerically pure beta-amino acids. It is also involved in the synthesis of mono and dihydroxylated derivatives of 2-aminocyclohexanecarboxylic acid by Diels-Alder adduct of ethyl(E)-3-nitroacrylate and furan.

Technology Process of (1S,2S)-2-Aminocyclohexanecarboxylic Acid

There total 53 articles about (1S,2S)-2-Aminocyclohexanecarboxylic 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: 100.0%

trans-2-(dibenzylamino)cyclohexane-1-carboxylic acid → (1R,2R)-2-aminocyclohexanecarboxylic Acid (5691-19-0,5691-20-3,24716-93-6,26685-83-6,45743-49-5,57090-28-5,75081-40-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 60h; under 1034.32 Torr;

DOI:10.1016/j.tetlet.2014.12.101

Reference yield: 92.0%

(1S,2S)-1-cyano-2-[N-(4-nitrobenzoyl)amino]cyclohexane (864445-67-0) → rac-trans-2-aminocyclohexanecarboxylic acid (5691-19-0,5691-20-3,24716-93-6,26685-83-6,45743-49-5,57090-28-5,75081-40-2)

Guidance literature:

With hydrogenchloride; at 90 ℃; for 120h;

DOI:10.1021/ja053486y DOI:10.1016/j.tet.2007.02.081

Reference yield: 89.0%

(3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid (506444-80-0) → rac-trans-2-aminocyclohexanecarboxylic acid (5691-19-0,5691-20-3,24716-93-6,26685-83-6,45743-49-5,57090-28-5,75081-40-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 22h; under 760.051 Torr;

DOI:10.1021/ja020879d

upstream raw materials:

(-)-(R,R)-N-benzoyl-trans-2-aminocyclohexanecarboxylic acid

trans-2-amino-1-cyclohexyl carboxylic acid ethyl ester

(1R,2R)-2-(benzyloxycarbonylamino)cyclohexylcarboxylic acid

(1R,2R)-2-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylic acid

Downstream raw materials:

(-)-(1R,2R)-2-(2,4-Dinitroanilino)cyclohexanecarboxylic acid

(1S,2S)-2-(benzothiazol-2-ylamino)cyclohexylmethanol

(1S,2S)-2-amino-cyclohexylmethanol

(1S,2S)-2-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexanecarboxylic acid

Refernces

• 1、 Chong, Hyun-Soon,Sun, Xiang,Chen, Yunwei,Wang, Meng. "Synthesis, characterization, and nucleophilic ring opening reactions of cyclohexyl-substituted β-haloamines and aziridinium ions". . p. 946 - 948. Retrieved 2015/01/30.
• 2、 -. "PEPTIDES AND PEPTIDOMIMETIC COMPOUNDS, THE MANUFACTURING THEREOF AS WELL AS THEIR USE FOR PREPARING A THERAPEUTICALLY AND/OR PREVENTIVELY ACTIVE PHARMACEUTICAL COMPOSITION". . . Retrieved 2010/04/25.