3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Base Information

• Chemical Name: 3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• CAS No.: 5654-86-4
• Molecular Formula: C₁₁H₁₈N₂O₂
• Molecular Weight: 210.276
• DSSTox Substance ID: DTXSID80951384
• Nikkaji Number: J92.058D
• Wikidata: Q72460568
• Metabolomics Workbench ID: 46467
• Mol file: 5654-86-4.mol

Synonyms:cyclo(Pro-Leu);cyclo(prolyl-leucyl);cyclo-(R-Pro-R-Leu);cyclo-(R-prolyl-R-leucyl)

Chemical Property of 3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Chemical Property:

• Melting Point: 163-165 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 427.6°Cat760mmHg
• PKA: 13.27±0.40(Predicted)
• Flash Point: 212.4°C
• PSA: 0.00000
• Density: 1.14g/cm³
• LogP: 0.00000
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 210.136827821
• Heavy Atom Count: 15
• Complexity: 288

Purity/Quality:

99%, ^*data from raw suppliers

Cyclo(leucyloprolyl) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CC1C(=O)N2CCCC2C(=O)N1

Technology Process of 3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

There total 20 articles about 3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione 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: 87.0%

cyclo(Z-L-Leu-D-Pro) (1380332-79-5) → (3S,8aR)-3-isobutyl-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione (2873-36-1,5654-86-4,19943-30-7,32510-93-3,36238-67-2,43041-29-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 24h;

DOI:10.1002/chem.201103143

Reference yield:

→ pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)- (2873-36-1,5654-86-4,19943-30-7,32510-93-3,36238-67-2,43041-29-8)

Guidance literature:

at 180 ℃; L-leucyl-DL-proline-anhydride; im Vakuum;

Reference yield:

DL-leucine ethyl ester (2899-43-6,75023-21-1) → pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)- (2873-36-1,5654-86-4,19943-30-7,32510-93-3,36238-67-2,43041-29-8)

Guidance literature:

With chloroform; lactam of -l-proline; Entfernen des Chlors aus dem Reaktionsprodukt; Saettigen der alkoh. Loesung mit Ammoniak;

upstream raw materials:

DL-leucine ethyl ester

L-prolyl-L-leucine

L-prolyl-L-leucylglycylglycine

Z-Leu-OH

Downstream raw materials:

(8aR)-3c-isobutyl-(8ar)-octahydro-pyrrolo[1,2-a]pyrazine

L-leucine

L-proline

Refernces

• 1、 Dewan, Faizunnahar,Domzalski, Alison,Kawamura, Akira,Margent, Liliana,Pilarsetty, Naga Vara Kishore,Vigo, Valeria,Xu, Yujia. "Unambiguous stereochemical assignment of cyclo(Phe-pro), cyclo(leu-pro), and cyclo(val-pro) by electronic circular dichroic spectroscopy". . . Retrieved 2021/10/12.
• 2、 Monbaliu, Jean-Christophe M.,Hansen, Finn K.,Beagle, Lucas K.,Panzner, Matthew J.,Steel, Peter J.,Todadze, Ekaterina,Stevens, Christian V.,Katritzky, Alan R.. "A new benzotriazole-mediated stereoflexible gateway to hetero-2,5- diketopiperazines". . p. 2632 - 2638. Retrieved 2012/04/17.