Cycloleucine

Base Information

• Chemical Name: Cycloleucine
• CAS No.: 52-52-8
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.159
• Hs Code.: 29224999
• Mol file: 52-52-8.mol

Synonyms:1-Amino-1-carboxycyclopentane;1-Aminocyclopentane-1-carboxylic acid;1-Aminocyclopentanecarboxylic acid;ACPC;Cycloleucin;NSC 1026;NSC 112194;NSC 112195;NSC 112197;WR 14997;

Chemical Property of Cycloleucine

Chemical Property:

• Appearance/Colour: white to beige crystalline flakes or powder
• Vapor Pressure: 0.00481mmHg at 25°C
• Melting Point: 320 °C (dec.)(lit.)
• Refractive Index: 1.522
• Boiling Point: 256.1 °C at 760 mmHg
• PKA: 2.38±0.20(Predicted)
• Flash Point: 108.7 °C
• PSA: 63.32000
• Density: 1.207 g/cm³
• LogP: 1.04280
• Storage Temp.: Store at RT.
• Water Solubility.: 5 g/100 mL
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 122

Purity/Quality:

98% ^*data from raw suppliers

Cycloleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xn,Xi
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C1)(C(=O)[O-])[NH3+]
• Uses: NMDA receptor antagonist, inhibits nucleic acid methylation; adrenergic agonist Cycloleucine can be used as a building block to synthesize: Phosphonylmethylaminocyclopentane-1-carboxylic acid by reacting with paraformaldehyde and diethylphosphite via Kabachnik-Field′s reaction. Benzo[b]thiophene-2-carboxylic acid {1-[1-(R)-(3-morpholin-4-ylpropylcarbamoyl)-2-phenylethylcarbamoyl]cyclopentyl}-amide, (MEN14268) as potential tachykinin NK2 receptor antagonist. Cycloleucine is a synthetic amino acid used in numerous biochemical transport studies

Technology Process of Cycloleucine

There total 13 articles about Cycloleucine 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: 99.0%

1-amino-1-cyanocyclopentane (49830-37-7) → 1-amino-1-cyclopentanecarboxylic acid (52-52-8)

Guidance literature:

With hydrogenchloride; water; In 1,4-dioxane; for 8h; Inert atmosphere; Reflux;

DOI:10.1021/acscombsci.6b00005

Reference yield: 75.0%

1,3-diazaspiro[4.4]nonane-2,4-dione (699-51-4) → 1-amino-1-cyclopentanecarboxylic acid (52-52-8)

Guidance literature:

With sodium hydroxide; Heating;

DOI:10.1021/jm00378a023

Reference yield:

→ 1-amino-1-cyclopentanecarboxylic acid (52-52-8)

Guidance literature:

With sulfuric acid; at 140 ℃;

DOI:10.1021/ja01189a085

upstream raw materials:

1-hydroxyamino-cyclopentanecarboxylic acid

potassium cyanide

cyclopentanone

1,3-diazaspiro[4.4]nonane-2,4-dione

Downstream raw materials:

2-(4-chloro-phenyl)-3-oxa-1-aza-spiro[4.4]non-1-en-4-one

3-oxa-1-azaspiro[4.4]nonane-2,4-dione

1-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid

1-Ureido-1-carboxy-cyclopentan

Refernces

• 1、 Stoyanov, Neyko,Marinov, Marin. "Two methods for spirothiohydantoin synthesis". . p. 680 - 685,6. Retrieved 2020/08/24.
• 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.