Piperazin-2-one

Base Information

• Chemical Name: Piperazin-2-one
• CAS No.: 5625-67-2
• Molecular Formula: C4H8N2O
• Molecular Weight: 100.12
• Hs Code.: 29349990
• European Community (EC) Number: 629-162-6
• NSC Number: 27441
• UNII: K9H2S9K98E
• DSSTox Substance ID: DTXSID10282698
• Nikkaji Number: J1.183.810C
• Wikidata: Q72500110
• Mol file: 5625-67-2.mol

Synonyms:Piperazin-2-one;5625-67-2;2-Piperazinone;2-Oxopiperazine;Piperazinone;Piperazine-2-one;2-ketopiperazine;MFCD01318687;K9H2S9K98E;3,4,5,6-tetrahydropyrazin-2-ol;NSC-27441;oxopiperazine;keto piperazine;3-oxopiperazine;piperazin-3-one;piperizin-2-one;piperazin-2-on;2-oxo piperazine;2-oxo-piperazine;2-Piperazine-one;NSC27441;2-Oxopiperazine--d6;2-Oxopiperazine, 97%;SCHEMBL5194;UNII-K9H2S9K98E;tetrahydro-2(1h)-pyrazinone;piperazin-2-one;DTXSID10282698;CHEBI:195071;BCP26674;CS-B0039;STR07287;NSC 27441;STK025825;STL301724;AKOS000269318;AKOS022140684;AC-1109;PB23229;PS-9326;2(1H)-PYRAZINONE, TETRAHYDRO-;BP-11215;SY002559;A8081;AM20100386;BB 0218076;FT-0649566;P1867;EN300-08705;W-203124;Z56968535;F1775-0070

Chemical Property of Piperazin-2-one

Chemical Property:

• Appearance/Colour: Colourless solid
• Vapor Pressure: 0.000738mmHg at 25°C
• Melting Point: 136-140 °C(lit.)
• Boiling Point: 307.1 °C at 760 mmHg
• PKA: 15.47±0.20(Predicted)
• Flash Point: 166.3 °C
• PSA: 41.13000
• Density: 1.053 g/cm³
• LogP: -0.63660
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Hygroscopic
• Solubility.: Chloroform
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.063662883
• Heavy Atom Count: 7
• Complexity: 81.8

Purity/Quality:

98% ^*data from raw suppliers

2-Piperazinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CNC(=O)CN1
• General Description: Piperazin-2-one is a cyclic amide derivative of piperazine that serves as a key scaffold in the design of potent BACE1 inhibitors for Alzheimer's disease (AD) therapy. It is structurally optimized to interact with the enzyme's active site, particularly the S2 subsite and flap region, enhancing binding affinity through hydrogen bonding and subsite occupancy. Piperazin-2-one class demonstrates therapeutic potential by inhibiting BACE1-mediated β-amyloid production, thereby mitigating AD pathology.

Technology Process of Piperazin-2-one

There total 24 articles about Piperazin-2-one 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: 91.0%

→ 2-Ketopiperazine (5625-67-2) + 1-[2-(3,4-difluorophenyl)ethyl]piperazin-2-one

Guidance literature:

Reference yield: 86.0%

diazoacetic acid ethyl ester (623-73-4) + ethylenediamine (107-15-3,85404-18-8) → 2-Ketopiperazine (5625-67-2)

Guidance literature:

With meso-tetraphenylporphyrin iron(III) chloride; In dichloromethane; at 22 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1142/S1088424610001982

Reference yield: 85.4%

chloroacetic acid ethyl ester (105-39-5) + ethylenediamine (107-15-3,85404-18-8) → 2-Ketopiperazine (5625-67-2)

Guidance literature:

chloroacetic acid ethyl ester; ethylenediamine; In methanol; at 0 - 5 ℃; for 4h;

With sodium methylate; In methanol; at 20 - 25 ℃; Solvent; Reagent/catalyst;

upstream raw materials:

ethanol

chloroacetic acid ethyl ester

ethylenediamine

formaldehyd

Downstream raw materials:

4-(3-Hydroxy-propyl)-piperazin-2-one

N,N'-dicyclohexyl-N-(3-nitrobenzoyl)urea

4-cyclohexyl-1,4-pyrazin-2-one

Refernces

Rational design of novel, potent piperazinone and imidazolidinone BACE1 inhibitors

10.1016/j.bmcl.2008.04.050

The study presents the rational design and synthesis of novel piperazinone and imidazolidinone inhibitors targeting BACE1, an enzyme implicated in Alzheimer's disease (AD) due to its role in producing β-amyloid peptides, which are toxic to neurons. The researchers aimed to develop potent inhibitors that could potentially slow or halt the progression of AD. The key chemicals used in the study include piperazinones and imidazolidinones, which were designed to interact with both the flap and the S20 pocket of BACE1. These cyclic amine motifs were specifically crafted to achieve both occupancy of the S2 subsite and formation of an additional hydrogen bond to the flap, enhancing the inhibitors' potency. The study involved extensive structure-activity relationship (SAR) analysis around these compounds to optimize their binding affinity and selectivity. The purpose of these chemicals was to serve as therapeutic agents that could reduce BACE1 activity, thereby decreasing AD-like pathology in transgenic mouse models.