Penigequinolone A

Base Information

• Chemical Name: Penigequinolone A
• CAS No.: 180045-91-4
• Molecular Formula: C27H33NO6
• Molecular Weight: 467.559
• DSSTox Substance ID: DTXSID401017599
• Nikkaji Number: J741.790J
• Wikidata: Q77279098
• Metabolomics Workbench ID: 115771
• Mol file: 180045-91-4.mol

Synonyms:penigequinolone A;penigequinolone B

Chemical Property of Penigequinolone A

Chemical Property:

• PSA: 97.25000
• LogP: 4.35030
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 467.23078777
• Heavy Atom Count: 34
• Complexity: 762

Purity/Quality:

97% ^*data from raw suppliers

Penigequinolone A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CCC(OC1)(C)C=CC2=C(C3=C(C=C2)NC(=O)C(C3(C4=CC=C(C=C4)OC)O)OC)O)C
• Isomeric SMILES: C[C@]1(CCC(CO1)(C)C)/C=C/C2=C(C3=C(C=C2)NC(=O)[C@@H]([C@]3(C4=CC=C(C=C4)OC)O)OC)O
• Uses: Penigequinoline A is a rare fungal metabolite produced by selected Penicillium species. Penigequinolone A is isolated as an inseparable mixture with its 19-epimer, penigequinolone B. Limited literature cites penigequinolone A as a pollen growth inhibitor. Penigequinolone A is a rare fungal metabolite produced by selected Penicillium species. Penigequinolone A is isolated as an inseparable mixture with its 19-epimer, penigequinolone B. Limited literature cites penigequinolone A as a pollen growth inhibitor. Penigequinolone A is penigequinoline A is a rare fungal metabolite produced by selected?Penicillium sp..

Technology Process of Penigequinolone A

There total 2 articles about Penigequinolone A 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:

(E)-4,5-dihydroxy-3-methoxy-4-(4-methoxyphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-6-[2-(2,5,5-trimethyltetrahydro-2H-pyran-2-yl)vinyl]-3,4-dihydroquinolin-2(1H)-one → (±)-penigequinolone A (180045-91-4) + (±)-penigequinolone B (180045-91-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 80 ℃; Overall yield = 94 percent; Overall yield = 16.9 mg; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.1c00042

Reference yield:

(E)-4,5-dihydroxy-3-methoxy-4-(4-methoxyphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-6-[2-(2,5,5-trimethyltetrahydro-2H-pyran-2-yl)vinyl]-3,4-dihydroquinolin-2(1H)-one → (±)-penigequinolone A (180045-91-4) + (±)-penigequinolone B (180045-91-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 80 ℃; Overall yield = 94 percent; Overall yield = 16.9 mg; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.1c00042

Refernces