27483-18-7

Basic information

• Product Name: (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione
• Synonyms: (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione;Cyclo(D-Val-L-Pro);(3R,8aS)-Hexahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione;Cyclo(L-prolyl-D-valine);Cyclo(L-prolyl-D-valyl);Cyclo-(S-Pro-R-Val);D-Valyl-L-proline diketopiperazine
• CAS NO: 27483-18-7
• Molecular Formula: C10H16N2O2
• Molecular Weight: 196.25
• Mol File: 27483-18-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 153-155℃
• Appearance: /
• CAS DataBase Reference: (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione(27483-18-7)
• EPA Substance Registry System: (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione(27483-18-7)

Safety Data

• Hazardous Substances Data: 27483-18-7(Hazardous Substances Data)

Usage

General Description

The chemical compound, (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione, is a pyrrolopyrazine derivative with a molecular formula C10H16N2O2. It is a cyclic compound with a pyrrolidine ring and a pyrazine ring, and a carbonyl group attached to the pyrazine ring. (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione is commonly used as a precursor in the synthesis of various pharmaceuticals and agrochemicals. It may also have potential applications in drug discovery and development due to its ability to modulate biological processes. Additionally, it may exhibit various properties such as antioxidant, antimicrobial, or anticancer activities, making it a subject of interest for further research in the field of medicinal chemistry.

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 13734-41-3 t-Boc-L-valine 
• 22838-58-0 Boc-D-Val-OH 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 3705-27-9 (S)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 916504-58-0 (8aS)-6,7,8,8a-tetrahydro-1-methoxypyrrolo[1,2-a]pyrazin-4(3H)-one 
• 916504-70-6 (3R,8aS)-6,7,8,8a-tetrahydro-1-methoxy-3-(1-methyethyl)pyrrolo[1,2-a]pyrazin-4(3H)-one 

Relevant articles and documents

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The use of Nbb resin in cyclic dipeptide ('diketopiperazine') synthesis

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Unambiguous stereochemical assignment of cyclo(Phe-pro), cyclo(leu-pro), and cyclo(val-pro) by electronic circular dichroic spectroscopy

2,5-diketopiperazines (DKPs) are cyclic dipeptides ubiquitously found in nature. In particular, cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro) are frequently detected in many microbial cultures. Each of these DKPs has four possible stereoisomers due to the presence of two chirality centers. However, absolute configurations of natural DKPs are often ambiguous due to the lack of a simple, sensitive, and reproducible method for stereochemical assignment. This is an important problem because stereochemistry is a key determinant of biological activity. Here, we report a synthetic DKP library containing all stereoisomers of cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro). The library was subjected to spectroscopic characterization using mass spectrometry, NMR, and electronic circular dichroism (ECD). It turned out that ECD can clearly differentiate DKP stereoisomers. Thus, our ECD dataset can serve as a reference for unambiguous stereochemical assignment of cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro) samples from natural sources. The DKP library was also subjected to a biological screening using assays for E. coli growth and biofilm formation, which revealed distinct biological effects of cyclo(D-Phe-L-Pro).

Diastereoselective alkylation of a proline-derived bicyclic lactim ether

N-Boc-protected L-proline (6) was converted into the bicyclic lactim ether (8aS)-6,7,8,8a-tetrahydro-1-methoxypyrrolo[1,2-a]pyrazin-4(3H)-one (5) in four steps (Scheme 1). Deprotonation with LDA or LHMDS and subsequent alkylation resulted in the diastereoisomeric products cis- and trans-9. The diastereoselectivity was mainly dependent on the electrophile. Whereas small alkyl halides gave preferably cis-9, sterically more-demanding alkyl halides resulted in cisltrans mixtures. Electrophiles bearing a π-system favored the trans-products 9. Some isolated cis- and tranx-lactim ethers 9 were converted to the corresponding diketopiperazines cis- and trans-10 by acid hydrolysis. The structures and configurations of several compounds were confirmed by NMR and NOE experiments, as well as by X-ray crystallography (Figs. 1-4).