(1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid

Base Information

• Chemical Name: (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid
• CAS No.: 111900-32-4
• Deprecated CAS: 130942-93-7,149881-50-5
• Molecular Formula: C7H11 N O4
• Molecular Weight: 173.169
• European Community (EC) Number: 634-585-4
• DSSTox Substance ID: DTXSID50920608
• Nikkaji Number: J257.596E
• Wikipedia: ACPD
• Wikidata: Q27070808
• Pharos Ligand ID: 8TRMRNLQA7Y6
• ChEMBL ID: CHEMBL34453
• Mol file: 111900-32-4.mol

Synonyms:(trans)-1-aminocyclopentyl-1,3-dicarboxylate;1-amino-1,3-dicarboxycyclopentane;1-amino-1,3-dicarboxycyclopentane, (cis)-(+-)-isomer;1-amino-1,3-dicarboxycyclopentane, (trans)-(+-)-isomer;1-amino-1,3-dicarboxycyclopentane, (trans)-isomer;1-amino-1,3-dicarboxycyclopentane, cis-(1R,3R)-isomer;1-amino-1,3-dicarboxycyclopentane, cis-(1S,3S)-isomer;1-amino-1,3-dicarboxycyclopentane, trans-(1R,3S)-isomer;1-amino-cyclopentyl-trans-1S,3R-dicarboxylate;1-aminocyclopentane-1,3-dicarboxylic acid;1-aminocyclopentyl-1,3-dicarboxylic acid;1R,3S-ACPD;1S,3R-ACPD;ACPD-1S,3R;cis-1-amino-1,3-cyclopentanecarboxylic acid;cis-ACPD;t-ACPD;trans-1-aminocyclopentane-1,3-dicarboxylate;trans-ACPD

Chemical Property of (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 6.39E-06mmHg at 25°C
• Melting Point: 248 °C (decomp)(Solv: ethanol (64-17-5); water (7732-18-5))
• Refractive Index: 1.563
• Boiling Point: 352.7°Cat760mmHg
• PKA: 2.11±0.40(Predicted)
• Flash Point: 167.1°C
• PSA: 100.62000
• Density: 1.452g/cm³
• LogP: 0.35350
• Storage Temp.: Store at RT
• Solubility.: ethanol: 0.24 mg/mL
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 173.06880783
• Heavy Atom Count: 12
• Complexity: 227

Purity/Quality:

99% ^*data from raw suppliers

trans-(1S,3R)-ACPD ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CC1C(=O)O)(C(=O)O)N
• Isomeric SMILES: C1C[C@](C[C@@H]1C(=O)O)(C(=O)O)N

Technology Process of (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid

There total 42 articles about (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic 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: 86.0%

dimethyl (1S,3R)-1-acetylaminocyclopentane-1,3-dicarboxylate (444809-82-9) → (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid (111900-32-4,477331-06-9)

Guidance literature:

With hydrogenchloride; for 5h; Heating;

DOI:10.1271/bbb.66.887

Reference yield: 80.0%

(1S,3R)-1-Ethoxycarbonylamino-cyclopentane-1,3-dicarboxylic acid (190510-46-4) → (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid (111900-32-4,477331-06-9)

Guidance literature:

With trimethylsilyl iodide; methyloxirane; In acetonitrile; at 40 ℃;

DOI:10.1016/S0957-4166(97)00060-8

Reference yield: 66.0%

(1S,3S)-1-tert-Butoxycarbonylamino-3-cyano-cyclopentanecarboxylic acid ethyl ester → trans-(+/-)-1-amino-1,3-cyclopentanedicarboxylic acid (39026-63-6,39026-64-7,56827-69-1,67684-64-4,89253-38-3,100910-67-6,111900-31-3,111900-32-4,111900-33-5,477331-06-9)

Guidance literature:

With hydrogenchloride; ammonium hydroxide; Dowex 50WX₈-100; 1.) reflux, 4 h;

DOI:10.1016/S0040-4039(98)00490-0

upstream raw materials:

(1S,3S)-ACPD

trans-1-aminocyclopentane-1,3-dicarboxylic acid

(1S,3R)-1-Ethoxycarbonylamino-cyclopentane-1,3-dicarboxylic acid

dimethyl (1S,3R)-1-acetylaminocyclopentane-1,3-dicarboxylate

Downstream raw materials:

(1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid

(1R,3S)-ACPD

(1R,3R)-ACPD

(1S,3S)-ACPD