(2R)-2-azaniumyloctanedioate

Base Information

• Chemical Name: (2R)-2-azaniumyloctanedioate
• CAS No.: 3054-07-7
• Molecular Formula: C8H15NO4
• Molecular Weight: 189.211
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID00427293
• Wikidata: Q72442046
• Mol file: 3054-07-7.mol

Synonyms:(2R)-2-azaniumyloctanedioate;DTXSID00427293

Chemical Property of (2R)-2-azaniumyloctanedioate

Chemical Property:

• Vapor Pressure: 5.16E-07mmHg at 25°C
• Melting Point: 222.9-225.1 °C
• Refractive Index: 1.4590 (estimate)
• Boiling Point: 385.5°Cat760mmHg
• PKA: 2.53±0.24(Predicted)
• Flash Point: 187°C
• PSA: 100.62000
• Density: g/cm³
• LogP: 1.13370
• Storage Temp.: 0-6°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 188.09228293
• Heavy Atom Count: 13
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

DL-2-Aminosuberic Acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCC(C(=O)[O-])[NH3+])CCC(=O)[O-]
• Isomeric SMILES: C(CC[C@H](C(=O)[O-])[NH3+])CCC(=O)[O-]

Technology Process of (2R)-2-azaniumyloctanedioate

There total 15 articles about (2R)-2-azaniumyloctanedioate 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%

1,1-diethyl 6-methyl 1-acetamidohexane-1,1,6-tricarboxylate (496921-59-6) → 2-amino-octanedioic acid (3054-07-7,19641-59-9)

Guidance literature:

With hydrogenchloride; water; for 6h; Reflux;

DOI:10.1016/j.bmcl.2010.09.100

Reference yield: 71.0%

methyl 6-iodohexanoate (14273-91-7) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → (2SR)-aminosuberic acid (3054-07-7,19641-59-9)

Guidance literature:

2-acetylaminomalonic acid diethyl ester; With sodium; In ethanol; for 0.5h;

methyl 6-iodohexanoate; In ethanol; Heating;

With hydrogenchloride; In water; Further stages.; Heating;

DOI:10.1021/ja029205t

Reference yield:

methyl 6-bromohexanoate (14273-90-6) → (2SR)-aminosuberic acid (3054-07-7,19641-59-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium iodide / tetrahydrofuran / Heating

2.1: sodium / ethanol / 0.5 h

2.2: ethanol / Heating

2.3: 71 percent / HCl / H₂O / Heating

With sodium; sodium iodide; In tetrahydrofuran; ethanol;

DOI:10.1021/ja029205t

upstream raw materials:

2-chloro-octanedioic acid

6-chlorohexanenitrile

2-acetylaminomalonic acid diethyl ester

6-bromo-hexanoic acid ethyl ester

Downstream raw materials:

N-(benzyloxycarbonyl)-L-α-aminosuberic acid

Z-Asu-OH

N-Carbobenzoxy-D-α-aminosuberinsaeure

(2R)-D-α-Aminosuberic acid

Refernces

• 1、 Wheatley, Nicole C.,Andrews, Katherine T.,Tran, Truc L.,Lucke, Andrew J.,Reid, Robert C.,Fairlie, David P.. "Antimalarial histone deacetylase inhibitors containing cinnamate or NSAID components". supporting information; experimental part. p. 7080 - 7084. Retrieved 2010/12/25.
• 2、 Kahnberg, Pia,Lucke, Andrew J.,Glenn, Matthew P.,Boyle, Glen M.,Tyndall, Joel D. A.,Parsons, Peter G.,Fairlie, David P.. "Design, synthesis, potency, and cytoselectivity of anticancer agents derived by parallel synthesis from α-aminosuberic acid". . p. 7611 - 7622. Retrieved 2007/10/03.