CIS-2-AMINO-1-CYCLOHEXANECARBOXYLIC ACID

Base Information

• Chemical Name: CIS-2-AMINO-1-CYCLOHEXANECARBOXYLIC ACID
• CAS No.: 5691-20-3
• Molecular Formula: C7H13NO2
• Molecular Weight: 143.186
• Hs Code.: 29224985
• Mol file: 5691-20-3.mol

Synonyms:C-ddG;Carbocyclic-2',3'-dideoxyguanosine;2-aminocyclohexanecarboxylic acid;

Chemical Property of CIS-2-AMINO-1-CYCLOHEXANECARBOXYLIC ACID

Chemical Property:

• Appearance/Colour: almost white to light beige crystalline powder
• Vapor Pressure: 0.00103mmHg at 25°C
• Melting Point: ~240 °C (dec.)
• Refractive Index: 1.503
• Boiling Point: 280 °C at 760 mmHg
• Flash Point: 123.1 °C
• PSA: 63.32000
• Density: 1.133g/cm³
• LogP: 1.28880

Purity/Quality:

98%Min ^*data from raw suppliers

cis-2-Aminocyclohexanecarboxylicacid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• General Description: CIS-2-AMINO-1-CYCLOHEXANECARBOXYLIC ACID is an enantiomerically pure amino acid derivative with potential therapeutic applications and utility in forming stable secondary structures in β-peptides. It can be synthesized via chemoselective and diastereoselective hydrogenation of quinazolinone intermediates, followed by hydrolysis, yielding the desired cis-isomer with high stereochemical purity. CIS-2-AMINO-1-CYCLOHEXANECARBOXYLIC ACID is structurally significant due to its cyclohexane backbone and functional groups, which contribute to its role in peptide design and medicinal chemistry.

Technology Process of CIS-2-AMINO-1-CYCLOHEXANECARBOXYLIC ACID

There total 68 articles about CIS-2-AMINO-1-CYCLOHEXANECARBOXYLIC 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: 99.0%

7-azabicyclo<4.2.0>octan-8-one (34102-49-3) → (1RS,2SR)-2-aminocyclohexanecarboxylic acid (5691-20-3)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 0.5h;

DOI:10.1055/s-2004-831224

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

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

2-phthalimidocyclohexanecarboxylic acid

Refernces

Synthesis of enantiopure cis- and trans-2-aminocyclohexane-1-carboxylic acids from octahydroquinazolin-4-ones

10.1016/j.tetasy.2004.08.032

The research describes a method for the synthesis of enantiomerically pure cis- and trans-2-aminocyclohexane-1-carboxylic acids, which are significant due to their potential therapeutic applications and role in forming stable secondary structures in β-peptides. The study utilizes 2-aminobenzamide as a chiral block to assemble quinazolinone, aiming to provide a new synthesis route for all four isomers of 2-aminocyclohexanecarboxylic acid. The process involves chemoselective and diastereoselective hydrogenation of 2,3-dihydro-3-[(S)-α-methylbenzyl]-4-quinazolinone to produce octahydroquinazolinones, which can be epimerized to form their respective stereoisomers. Hydrolysis of these octahydroquinazolinones with HCl yields the desired enantiomerically pure amino acids.