Pilosinine

Base Information

• Chemical Name: Pilosinine
• CAS No.: 38993-86-1
• Molecular Formula: C₉H₁₂N₂O₂
• Molecular Weight: 180.206
• ChEMBL ID: CHEMBL313046
• DSSTox Substance ID: DTXSID301167533
• Nikkaji Number: J442.728I
• Wikidata: Q110183808
• Mol file: 38993-86-1.mol

Synonyms:(4R)-4-((3-methylimidazol-4-yl)methyl)oxolan-2-one;pilosinine

Chemical Property of Pilosinine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 180.089877630
• Heavy Atom Count: 13
• Complexity: 208

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1C=NC=C1CC2CC(=O)OC2
• Isomeric SMILES: CN1C=NC=C1C[C@@H]2CC(=O)OC2

Technology Process of Pilosinine

There total 12 articles about Pilosinine 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:

[(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7) + C7H11NO2 → (+)-pilosinine (38993-86-1)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 168h; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.151945

Reference yield:

1-methylimidazole-5-carbaldehyde (39021-62-0) → (+)-pilosinine (38993-86-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) NaH / THF, 0 deg C

2: 95 percent / H₂ / 10percent Pd-C / methanol

3: 1) NaN(SiMe₃)2 / 1) THF, -78 deg C, 3 h, 2) -60 deg C, 3 h

4: Zn(BH₄)2 / diethyl ether / 120 h / Ambient temperature

5: 95percent aq. CF₃COOH / 0 °C

With zinc(II) tetrahydroborate; hydrogen; sodium hexamethyldisilazane; sodium hydride; trifluoroacetic acid; palladium on activated charcoal; In methanol; diethyl ether;

DOI:10.1016/S0040-4039(00)92211-1

Reference yield:

(S)-4-Benzyl-3-[(E)-3-(3-methyl-3H-imidazol-4-yl)-acryloyl]-oxazolidin-2-one (142143-25-7) → (+)-pilosinine (38993-86-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / H₂ / 10percent Pd-C / methanol

2: 1) NaN(SiMe₃)2 / 1) THF, -78 deg C, 3 h, 2) -60 deg C, 3 h

3: Zn(BH₄)2 / diethyl ether / 120 h / Ambient temperature

4: 95percent aq. CF₃COOH / 0 °C

With zinc(II) tetrahydroborate; hydrogen; sodium hexamethyldisilazane; trifluoroacetic acid; palladium on activated charcoal; In methanol; diethyl ether;

DOI:10.1016/S0040-4039(00)92211-1

upstream raw materials:

pilosine

1-methylimidazole-5-carbaldehyde

succinic acid diethyl ester

pilosine

Downstream raw materials:

(3S)-3r-benzoyl-4t-(3-methyl-3H-imidazol-4-ylmethyl)-dihydro-furan-2-one

o-Fluorepiisopilosin

pilocarpine

(3S)-3r-((S)-hydroxy-phenyl-methyl)-4t-(3-methyl-3H-imidazol-4-ylmethyl)-dihydro-furan-2-one

Refernces

• 1、 Schrank, Cassandra L.,Danneman, Michael W.,Prebihalo, Emily A.,Anderson, Robert E.,Gibson, Tyler J.,Wuest, William M.,Mullins, Richard J.. "Total synthesis of (+)-pilosinine via a stereodivergent conjugate addition strategy". . . Retrieved 2020/04/27.
• 2、 Tedeschi,Kamionsky,Zeider,et al.. "Isolation, characterization, and synthesis of trans pilosine stereoisomers occurring in nature. Circular dichroism and mass spectral studies". . p. 1864 - 1870. Retrieved 2007/10/04.