561303-30-8

Basic information

• Product Name: 2,5-Piperazinedione, 1-(phenylmethyl)-3-(2-propynyl)-
• CAS NO: 561303-30-8
• Molecular Formula: C14H14N2O2
• Molecular Weight: 242.277
• Mol File: 561303-30-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,5-Piperazinedione, 1-(phenylmethyl)-3-(2-propynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Piperazinedione, 1-(phenylmethyl)-3-(2-propynyl)-(561303-30-8)
• EPA Substance Registry System: 2,5-Piperazinedione, 1-(phenylmethyl)-3-(2-propynyl)-(561303-30-8)

Safety Data

• Hazardous Substances Data: 561303-30-8(Hazardous Substances Data)

Upstream product

• 20898-44-6 Boc-His(Bzl)-OH 
• 53386-64-4 methyl 2-(benzylamino)acetate 
• 1027236-10-7 {benzyl-[3-(1-benzyl-1H-imidazol-4-yl)-2-tert-butoxycarbonylamino-propionyl]-amino}-acetic acid methyl ester 

Downstream Products

• 561303-39-7 4-benzyl-3,6-dioxo-2-prop-2-ynylpiperazine-1-carboxylic acid methyl ester 

Relevant articles and documents

Synthesis of 2,6-bridged piperazine-3-ones by N-acyliminium ion chemistry

Several 2-substituted and 2,5-disubstituted piperazine-3,6-diones were synthesized starting from readily available α-amino acids. After activation of a lactam carbonyl via introduction of a methoxycarbonyl group onto nitrogen, this carbonyl was selectively reduced. Treatment of the resulting urethane with protic acid generated the corresponding N-acyliminium ion, which was trapped by a nucleophilic C2-side chain to provide 2,6-bridged piperazine-3-ones. Several aromatic, heteroaromatic, and nonaromatic side chains were used as π-nucleophiles. In addition, the effect of the presence of a C5-methyl group on the stereochemical outcome of the cyclization was examined.