143673-66-9

Basic information

• Product Name: (R)-3-Isopropyl-2,5-piperazinedione
• Synonyms: (R)-3-Isopropyl-2,5-piperazinedioneCyclo-(glycyl-D-valine);(R)-3-isopropyl-2,5-piperizinedione;(3R)-3-Isopropyl-2,5-piperazinedione;(R)-3-Isopropyl-2,5-piperazinedione,99%e.e.;(R)-(-)-3-ISOPROPYL-2,5-PIPERAZINEDIONE;(R)-3-ISOPROPYL-2,5-PIPERAZINEDIONE;RARECHEM AK HZ 0043;CYCLO-(GLYCYL-D-VALINE)
• CAS NO: 143673-66-9
• Molecular Formula: C₇H₁₂N₂O₂
• Molecular Weight: 156.18
• Product Categories: ISOPROPYL;pharmacetical;Chiral Building Blocks;Heterocyclic Building Blocks;Piperazines
• Mol File: 143673-66-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 258-262 °C(lit.)
• Boiling Point: 280.42°C (rough estimate)
• Flash Point: 216.6 °C
• Appearance: white to light yellow crystal powder
• Density: 1.1832 (rough estimate)
• Vapor Pressure: 3.87E-08mmHg at 25°C
• Refractive Index: 1.4880 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 13.12±0.40(Predicted)
• Water Solubility: 23 g/L (22 ºC)
• BRN: 82869
• CAS DataBase Reference: (R)-3-Isopropyl-2,5-piperazinedione(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-Isopropyl-2,5-piperazinedione(143673-66-9)
• EPA Substance Registry System: (R)-3-Isopropyl-2,5-piperazinedione(143673-66-9)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25-36/37/39-26
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 143673-66-9(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 143673-66-9 differently. You can refer to the following data:
1. (R)-3-Isopropyl-2,5-piperazinedione acts as a useful reagent in the synthesis of (R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine.
2. Chiral auxiliary developed by Professor Sch?llkopf for the enantioselective synthesis of α-amino acids.

InChI:InChI=1/C7H12N2O2/c1-4(2)6-7(11)8-3-5(10)9-6/h4,6H,3H2,1-2H3,(H,8,11)(H,9,10)/t6-/m1/s1

Upstream product

• 640-68-6 D-Val-OH 
• 3479-71-8 Boc-D-Val-Gly-OEt 
• 1685-33-2 N-[(benzyloxy)carbonyl]-D-valine 
• 22838-58-0 Boc-D-Val-OH 
• 850312-86-6 ((R)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-acetic acid methyl ester 
• 43089-05-0 D-valine N-carboxy anhydride 
• 459-73-4 GlyOEt*HCl 
• 32402-31-6 N-benzyloxycarbonyl-(2R)-valinylglycine methyl ester 

Downstream Products

• 110117-71-0 (2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine 
• 479681-63-5 (R)-3-Isopropyl-1-(4-methoxy-benzyl)-piperazine-2,5-dione 
• 207284-25-1 (2R)-2-(1-methylethyl)piperazine 
• 143730-33-0 (3R,6S)-6-benzyloxymethyl-3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazine 
• 143673-70-5 ethyl (3R,6S)-3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazin-6-ylacetate 
• 143730-34-1 (3R,6S)-6-benzyl-3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazine 
• 3350-55-8 (R)-(-)-valine ethyl ester 
• 479681-67-9 C₂₂H₂₆N₂O₃C₂₂H₂₆N₂O₃C₈H₆ 
• 479681-66-8 C₂₂H₂₆N₂O₃C₂₂H₂₆N₂O₃C₈H₆ 
• 479681-65-7 (R)-4-Benzyl-3-isopropyl-1-(4-methoxy-benzyl)-piperazine-2,5-dione 
• 479681-64-6 (R)-1-Benzyl-3-isopropyl-4-(4-methoxy-benzyl)-piperazine-2,5-dione 
• 479681-62-4 (R)-1-Benzyl-3-isopropyl-piperazine-2,5-dione 

Relevant articles and documents

Stereostructure Clarifying Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone B. A Highly Acid-Labile N-Protecting Group for Amides ?

The 5S, 8′R, and 10′R configurations of militarinone B (3), which is a natural product from Paecilomyces militaris, should equal those in its biosynthetic precursor, militarinone C. The configuration at C-1′ emerged from syntheses of the militarinone B candidates 1′′S- and 1′′R-(5S,8′R,10′R)-3 from the building blocks 9, 11, 14, and 15a while introducing TMB as a more acid-labile N-protecting group for β-ketoamides than DMB. Comparisons of 1′′S- and 1′′R-(5S,8′R,10′R)-3 with natural militarinone B (3; reisolated from Nature) revealed identity versus distinctness.

Stereoselective ring contraction of 2,5-diketopiperazines: An innovative approach to the synthesis of promising bioactive 5-membered scaffolds

Ring contraction of 2,5-diketopiperazines by TRAL-alkylation led us to the stereoselective synthesis of original pyrrolidine-2,4-diones, a novel series of promising molecules with moderate anti-proliferative activity on breast cancer cells.

An improved large scale synthesis of the Schoellkopf chiral auxiliaries: (2R)-and (2S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine

Syntheses of the Schoellkopf chiral auxiliaries have been carried out on large scale in high overall yields from D- and L-valine. This method avoids the use of highly toxic phosgene or triphosgene, low-temperature reactions, and unstable intermediates.