Peramine

Base Information

• Chemical Name: Peramine
• CAS No.: 102482-94-0
• Molecular Formula: C₁₂H₁₇N₅O
• Molecular Weight: 247.3
• DSSTox Substance ID: DTXSID10145178
• Nikkaji Number: J292.156A
• Wikidata: Q83009587
• Mol file: 102482-94-0.mol

Synonyms:peramine

Chemical Property of Peramine

Chemical Property:

• Vapor Pressure: 4.12E-06mmHg at 25°C
• Boiling Point: 384.3°Cat760mmHg
• Flash Point: 186.2°C
• PSA: 88.31000
• Density: 1.33g/cm³
• LogP: 1.24460
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 247.14331018
• Heavy Atom Count: 18
• Complexity: 386

Purity/Quality:

99% ^*data from raw suppliers

Peramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=CN2C=CC=C2C1=O)CCCN=C(N)N
• Uses: Peramine is a naturally occuring pyrrolopyrazine alkaloid produced by endophytes that protect the grass against grazing by mammals and insects. Peramine is a potent feeding deterrent against both larvae and major pest of pernnial ryegrass.

Technology Process of Peramine

There total 16 articles about Peramine 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: 83.0%

C22H33N5O5 → peramine (102482-94-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2017.05.004

Reference yield:

pent-1-yn-5-ol (5390-04-5) → peramine (102482-94-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide

2.1: copper acetylacetonate; 3,4,7,8-Tetramethyl-o-phenanthrolin / N,N-dimethyl-formamide / 0.5 h / 80 °C / Inert atmosphere

2.2: 2 h / 60 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C

4.1: azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine / tetrahydrofuran / 40 °C

5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C

With 1H-imidazole; azodicarboxylic acid bis(2-methoxyethyl) ester; copper acetylacetonate; 3,4,7,8-Tetramethyl-o-phenanthrolin; tetrabutyl ammonium fluoride; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2017.05.004

Reference yield:

[(5-bromo-4-pentyn-1-yl)oxy](tert-butyl)dimethyl-silane (474022-55-4) → peramine (102482-94-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: copper acetylacetonate; 3,4,7,8-Tetramethyl-o-phenanthrolin / N,N-dimethyl-formamide / 0.5 h / 80 °C / Inert atmosphere

1.2: 2 h / 60 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C

3.1: azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine / tetrahydrofuran / 40 °C

4.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C

With azodicarboxylic acid bis(2-methoxyethyl) ester; copper acetylacetonate; 3,4,7,8-Tetramethyl-o-phenanthrolin; tetrabutyl ammonium fluoride; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2017.05.004

upstream raw materials:

2-methylisothiourea sulphate

3-(3-aminopropyl)-2-methylpyrrolo<1,2-a>pyrazin-1-(2H)-one

methyl Pyrrole-2-carboxylate

3-hydroxymethyl-2-methylpyrrolo<1,2-a>pyrazin-1(2H)-one