Pyrrolostatin

Base Information

• Chemical Name: Pyrrolostatin
• CAS No.: 144314-68-1
• Molecular Formula: C15H21NO2
• Molecular Weight: 247.3327
• Nikkaji Number: J549.641A
• Wikipedia: Pyrrolostatin
• Metabolomics Workbench ID: 115937
• Mol file: 144314-68-1.mol

Synonyms:4-geranylpyrrole-2-carboxylic acid;pyrrolostatin

Chemical Property of Pyrrolostatin

Chemical Property:

• Appearance/Colour: Yellowish Powder
• Vapor Pressure: 1.51E-08mmHg at 25°C
• Boiling Point: 440.8 °C at 760 mmHg
• Flash Point: 220.4 °C
• PSA: 53.09000
• Density: 1.066 g/cm³
• LogP: 3.94810
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 247.157228913
• Heavy Atom Count: 18
• Complexity: 340

Purity/Quality:

98.5% ^*data from raw suppliers

PYRROLOSTATIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCC1=CNC(=C1)C(=O)O)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC1=CNC(=C1)C(=O)O)/C)C

Technology Process of Pyrrolostatin

There total 19 articles about Pyrrolostatin 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: 80.0%

C17H23NO4 → pyrrolostatin (144314-68-1)

Guidance literature:

With lithium hydroxide; In methanol; water; at 20 ℃;

DOI:10.1016/j.tetlet.2016.05.010

Reference yield: 73.0%

ethyl 4-(3,7-dimethylocta-2,6-dienyl)pyrrole-2-carboxylate (247026-84-2) → pyrrolostatin (144314-68-1)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; water; at 40 ℃; for 19h;

DOI:10.1021/jo990666f

Reference yield: 48.0%

3-geranyl pyrrole + trifluoroacetyl chloride (76-02-8) → C15H21NO2 + pyrrolostatin (144314-68-1)

Guidance literature:

3-geranyl pyrrole; trifluoroacetyl chloride; In diethyl ether; at 20 ℃; for 2h; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; at 75 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c5ob01066g

upstream raw materials:

ethyl 4-(3,7-dimethylocta-2,6-dienyl)pyrrole-2-carboxylate

(E)-4,8-dimethylnona-3,7-dien-1-ol

3,7-dimethyl-2,6-octadienal

Geraniol