Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-

Base Information

• Chemical Name: Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-
• CAS No.: 14705-60-3
• Deprecated CAS: 1290538-93-0
• Molecular Formula: C₁₄H₁₆N₂O₂
• Molecular Weight: 244.293
• NSC Number: 646119,255998
• DSSTox Substance ID: DTXSID30933019
• Nikkaji Number: J1.369.943G
• Wikidata: Q82908802
• Metabolomics Workbench ID: 126005
• ChEMBL ID: CHEMBL1990465
• Mol file: 14705-60-3.mol

Synonyms:cyclo(L-Phe-L-Pro);cyclo(Phe-Pro);cyclo(phenylalanyl-prolyl)

Chemical Property of Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-

Chemical Property:

• Boiling Point: 509.5°Cat760mmHg
• PKA: 13.21±0.40(Predicted)
• Flash Point: 262°C
• PSA: 49.41000
• Density: 1.26g/cm³
• LogP: 0.98520
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 244.121177757
• Heavy Atom Count: 18
• Complexity: 350

Purity/Quality:

97% ^*data from raw suppliers

Cyclo(Phe-Pro) 98.10% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC2C(=O)NC(C(=O)N2C1)CC3=CC=CC=C3

Technology Process of Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-

There total 60 articles about Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)- 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%

L-phenylalaninyl-L-proline methyl ester hydrochloride (77100-17-5) → (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione (5654-85-3,14705-60-3,26488-24-4,32021-26-4,43041-16-3,43041-30-1,3705-26-8)

Guidance literature:

With water; triethylamine; at 140 ℃; for 0.166667h; microwave irradiation;

DOI:10.1016/j.tet.2006.05.010

Reference yield: 88.0%

t-butyloxycarbonyl-L-phenylalanyl-L-proline methyl ester (38017-89-9) → (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione (5654-85-3,14705-60-3,26488-24-4,32021-26-4,43041-16-3,43041-30-1,3705-26-8)

Guidance literature:

In 1,4-dioxane; water; at 130 ℃; for 4h;

DOI:10.1016/j.tetlet.2009.12.134

Reference yield: 82.0%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione (5654-85-3,14705-60-3,26488-24-4,32021-26-4,43041-16-3,43041-30-1,3705-26-8)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(01)02005-6

upstream raw materials:

Z-DL-Phe-OH

acetone

1-(3,4,5-tris(octadecyloxy)benzyl)-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine

(1S)-methyl 2-[(S)-2-amino-3-phenylpropanoyl]cyclopentanecarboxylate

Downstream raw materials:

N-L-prolyl-L-phenylalanine

[(S)-1-((3S,8aS)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-carbamic acid benzyl ester

N--Phe-Pro-Lactam

N-(d-Lysergyl-L-valyl)-L-phenylalanyl-L-prolin-lactam