(R)-3-Isopropyl-2,5-piperazinedione

Base Information

• Chemical Name: (R)-3-Isopropyl-2,5-piperazinedione
• CAS No.: 143673-66-9
• Molecular Formula: C7H12N2O2
• Molecular Weight: 156.18
• Hs Code.: 29335995
• European Community (EC) Number: 841-336-5
• DSSTox Substance ID: DTXSID20931983
• Nikkaji Number: J1.154.831H
• Wikidata: Q72486207
• Mol file: 143673-66-9.mol

Synonyms:143673-66-9;(R)-3-ISOPROPYL-2,5-PIPERAZINEDIONE;(R)-3-Isopropylpiperazine-2,5-dione;(R)-(-)-3-Isopropyl-2,5-piperazinedione;(3R)-3-propan-2-ylpiperazine-2,5-dione;MFCD00210060;(R)-3-ISOPROPYL-PIPERAZINE-2,5-DIONE;SCHEMBL5008495;DTXSID20931983;IULFBTHVPRNQCG-ZCFIWIBFSA-N;AKOS006240444;AM84396;(3R)-3-Isopropyl-2,5-piperazinedione;AS-17789;EN300-258662;F15005;(R)-(-)-3-Isopropyl-2,5-piperazinedione, 97%;3-(Propan-2-yl)-3,6-dihydropyrazine-2,5-diol;A808096;J-007854;(3R)-3-(PROPAN-2-YL)PIPERAZINE-2,5-DIONE

Chemical Property of (R)-3-Isopropyl-2,5-piperazinedione

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 3.87E-08mmHg at 25°C
• Melting Point: 258-262 °C(lit.)
• Refractive Index: 1.459
• Boiling Point: 445.7 °C at 760 mmHg
• PKA: 13.12±0.40(Predicted)
• Flash Point: 216.6 °C
• PSA: 58.20000
• Density: 1.087 g/cm³
• LogP: -0.08540
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: 23 g/L (22 ºC)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 156.089877630
• Heavy Atom Count: 11
• Complexity: 189

Purity/Quality:

99% ^*data from raw suppliers

(R)-3-Isopropyl-2,5-piperazinedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1C(=O)NCC(=O)N1
• Isomeric SMILES: CC(C)[C@@H]1C(=O)NCC(=O)N1
• Uses: (R)-3-Isopropyl-2,5-piperazinedione acts as a useful reagent in the synthesis of (R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine. Chiral auxiliary developed by Professor Sch?llkopf for the enantioselective synthesis of α-amino acids.

Technology Process of (R)-3-Isopropyl-2,5-piperazinedione

There total 11 articles about (R)-3-Isopropyl-2,5-piperazinedione 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: 93.0%

Boc-D-Val-Gly-OEt (3479-71-8) → H-Val-Gly-OH (71698-68-5,6491-60-7) + (R)-3-(1-methylethyl)-piperazine-2,5-one (143673-66-9)

Guidance literature:

With water; In N,N-dimethyl-formamide; at 150 ℃; for 2.5h; enantioselective reaction; Microwave irradiation;

DOI:10.1016/j.bioorg.2010.05.002

Reference yield: 75.0%

((R)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-acetic acid methyl ester (850312-86-6) → (R)-3-(1-methylethyl)-piperazine-2,5-one (143673-66-9)

Guidance literature:

In water; at 150 ℃; for 0.25h; microwave irradiation;

DOI:10.1016/j.tetlet.2006.05.013

Reference yield: 70.0%

D-valine N-carboxy anhydride (43089-05-0) + GlyOEt*HCl (459-73-4) → (R)-3-(1-methylethyl)-piperazine-2,5-one (143673-66-9)

Guidance literature:

D-valine N-carboxy anhydride; GlyOEt*HCl; With triethylamine; In tetrahydrofuran; chloroform; at -70 ℃;

In toluene; Further stages.; Heating;

DOI:10.1016/j.tetlet.2004.09.113

upstream raw materials:

N-benzyloxycarbonyl-(2R)-valinylglycine methyl ester

D-valine N-carboxy anhydride

GlyOEt*HCl

((R)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-acetic acid methyl ester

Downstream raw materials:

(2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine

(R)-1-Benzyl-3-isopropyl-piperazine-2,5-dione

(R)-3-Isopropyl-1-(4-methoxy-benzyl)-piperazine-2,5-dione

(R)-(-)-valine ethyl ester

Refernces

• 1、 -. "MACROCYCLIC COMPOUNDS AS PROTEASOME INHIBITORS". Paragraph 0560. . Retrieved 2019/05/02.
• 2、 Carlsson, Anna-Carin,Jam, Fariba,Tullberg, Marcus,Pilotti, ?ke,Ioannidis, Panos,Luthman, Kristina,Gr?tli, Morten. "Microwave-assisted synthesis of the Sch?llkopf chiral auxiliaries: (3S)- and (3R)-3,6-dihydro-2,5-diethoxy-3-isopropyl-pyrazine". . p. 5199 - 5201. Retrieved 2007/10/03.