(1S,2S)-2-Aminocyclopentanecarboxylic acid

Base Information

• Chemical Name: (1S,2S)-2-Aminocyclopentanecarboxylic acid
• CAS No.: 64191-13-5
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.159
• Hs Code.: 2922499990
• UNII: T3QGG29GOX
• DSSTox Substance ID: DTXSID90451143
• Nikkaji Number: J685.321H
• Wikidata: Q27467516
• Mol file: 64191-13-5.mol

Synonyms:(1S,2S)-2-aminocyclopentane-1-carboxylic acid;ACPC cpd

Chemical Property of (1S,2S)-2-Aminocyclopentanecarboxylic acid

Chemical Property:

• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 146-147 °C(Solv: ethanol (64-17-5); ethyl acetate (141-78-6))
• Refractive Index: 1.515
• Boiling Point: 264.72 °C at 760 mmHg
• PKA: 3.87±0.20(Predicted)
• Flash Point: 113.899 °C
• PSA: 63.32000
• Density: 1.19 g/cm³
• LogP: 0.89870
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 124

Purity/Quality:

99.3% ^*data from raw suppliers

(1S,2S)-2-Aminocyclopentanecarboxylicacid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(C1)N)C(=O)O
• Isomeric SMILES: C1C[C@@H]([C@H](C1)N)C(=O)O

Technology Process of (1S,2S)-2-Aminocyclopentanecarboxylic acid

There total 14 articles about (1S,2S)-2-Aminocyclopentanecarboxylic 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: 71.0%

(trans-(1S,2S)-2-aminocyclopentanecarbonyl)-(R)-(+)-α-methylbenzylamine (136237-71-3) → (+)-(1S,2S)-2-aminocyclopentane-1-carboxylic acid (64191-13-5,37910-65-9)

Guidance literature:

With hydrogenchloride; for 8h; Heating;

DOI:10.1021/jo00023a033

Reference yield: 40.0%

(+)-tert-butyl (1S,2S)-2-aminocyclopentane-1-carboxylate (188818-72-6) → (+)-(1S,2S)-2-aminocyclopentane-1-carboxylic acid (64191-13-5,37910-65-9)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 12h;

DOI:10.1016/j.tet.2006.06.040

Reference yield:

meso-6-(4-nitrobenzoyl)-6-azabicyclo[3.1.0]hexane → (+)-(1S,2S)-2-aminocyclopentane-1-carboxylic acid (64191-13-5,37910-65-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Gd(OiPr)3; (2S,3R,4R)-2-(Ph₂P(O)CH₂)-3-OH-4-O-(2-OH-4,5-diF-Ph)-THP; 2,6-dimethylphenol / trifluoroacetic acid / various solvent(s) / 14 h / 40 °C

2: aq. HCl / 72 h / 90 °C

With hydrogenchloride; gadolinium(III) isopropoxide; 2.6-dimethylphenol; 1,5-anhydro-2,6-dideoxy-3-O-(4,5-difluoro-2-hydroxyphenyl)-6-(diphenylphosphinyl)-D-arabino-hexitol; trifluoroacetic acid; In various solvent(s);

DOI:10.1021/ja053486y

upstream raw materials:

(trans-(1S,2S)-2-aminocyclopentanecarbonyl)-(R)-(+)-α-methylbenzylamine

(+)-tert-butyl (1S,2S)-2-aminocyclopentane-1-carboxylate

(1S,2S)-2-[(1'S)-phenylethyl]aminocyclopentanecarboxylic acid

(+)-tert-butyl (1S,2S)-2-((mesitylmethyl)amino)cyclopentanecarboxylate

Downstream raw materials:

N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-trans-(1S,2S)-2-aminocyclopentanecarboxylic acid methyl ester

(1S)-trans-2-<<(1,1-dimethylethoxy)carbonyl>amino>cyclopentanecarboxylic acid

Refernces

• 1、 Mita, Tsuyoshi,Fujimori, Ikuo,Wada, Reiko,Wen, Jianfeng,Kanai, Motomu,Shibasaki, Masakatsu. "Catalytic enantioselective desymmetrization of meso-N-acylaziridines with TMSCN". . p. 11252 - 11253. Retrieved 2007/10/03.
• 2、 Yamazaki, Toshimasa,Zhu, Yun-Fei,Probstl, Albert,Chadha, Raj K.,Goodman, Murray. "Probing a Molecular Model of Taste Utilizing Peptidomimetic Stereoisomers of 2-Aminocyclopentanecarboxylic Acid Methyl Ester". . p. 6644 - 6655. Retrieved 2007/10/02.