Piperafizine B

Base Information

• Chemical Name: Piperafizine B
• CAS No.: 74720-33-5
• Molecular Formula: C18H14 N2 O2
• Molecular Weight: 290.321
• Hs Code.: 2933599090
• Nikkaji Number: J1.324.107D,J672.514G
• Metabolomics Workbench ID: 133016
• ChEMBL ID: CHEMBL367764
• Mol file: 74720-33-5.mol

Synonyms:3,6-dibenzylidene-2,5-dioxopiperazine;piperafizine B

Chemical Property of Piperafizine B

Chemical Property:

• Vapor Pressure: 1.37E-16mmHg at 25°C
• Boiling Point: 646.2°C at 760 mmHg
• Flash Point: 258.2°C
• PSA: 66.24000
• Density: 1.278g/cm³
• LogP: 1.54540
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 290.105527694
• Heavy Atom Count: 22
• Complexity: 449

Purity/Quality:

98% ^*data from raw suppliers

PiperafizineB ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=C2C(=O)NC(=CC3=CC=CC=C3)C(=O)N2
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/2\NC(=O)/C(=C/C3=CC=CC=C3)/NC2=O
• Uses: Piperafizine B (cas# 74720-33-5) is used as a reagent in the stereoselective preparation of diketopiperazine bisepoxides

Technology Process of Piperafizine B

There total 7 articles about Piperafizine B 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%

benzaldehyde (100-52-7) + 1,4-diacetylpiperazine → (Z)-3-(Z)-6-dibenzylidene-2,5-piperazinedione (74720-33-5)

Guidance literature:

With triethylamine; N,N-dimethyl-formamide; for 21h; Heating;

DOI:10.1071/CH9841791

Reference yield: 91.0%

benzaldehyde (100-52-7) + 1-acetyl-3-[(Z)-benzylidene]-2,5-piperazinedione (30166-29-1,30166-30-4,41808-11-1) → (Z)-3-(Z)-6-dibenzylidene-2,5-piperazinedione (74720-33-5)

Guidance literature:

With potassium fluoride on basic alumina; Irradiation;

Reference yield: 75.0%

N,N'-diacetylpiperazin-2,5-dione (3027-05-2) + benzaldehyde (100-52-7) → (Z)-3-(Z)-6-dibenzylidene-2,5-piperazinedione (74720-33-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 120 ℃; for 12h;

DOI:10.1021/acs.orglett.1c01894

upstream raw materials:

benzaldehyde

1-acetyl-3-[(Z)-benzylidene]-2,5-piperazinedione

1,4-diacetyl-(Z)-3-benzylidene-2,5-piperazinedione

N,N'-diacetylpiperazin-2,5-dione

Downstream raw materials:

1,4-dimethyl-(Z)-3-(Z)-6-dibenzylidene-2,5-piperazinedione

(+/-)-(Z)-6-benzyl-3-benzylidenepiperazine-2,5-dione

(+/-)-cis-3,6-dibenzylpiperazine-2,5-dione

(+/-)-trans-3,6-dibenzylpiperazine-2,5-dione

Refernces

• 1、 Ge, Yao,Han, Zhaobin,Wang, Zheng,Ding, Kuiling. "Ir-Catalyzed Double Asymmetric Hydrogenation of 3,6-Dialkylidene-2,5-diketopiperazines for Enantioselective Synthesis of Cyclic Dipeptides". supporting information. p. 8981 - 8988. Retrieved 2019/06/13.
• 2、 Loughlin, Wendy A.,Marshall, Raymond L.,Carreiro, Adelina,Elson, Kathryn E.. "Solution-phase combinatorial synthesis and evaluation of piperazine-2,5- dione derivatives". . p. 91 - 94. Retrieved 2007/10/03.