Xerulin

Base Information

• Chemical Name: Xerulin
• CAS No.: 132971-61-0
• Molecular Formula: C₁₈H₁₄O₂
• Molecular Weight: 262.308
• Nikkaji Number: J1.181.436K
• Mol file: 132971-61-0.mol

Synonyms:xerulin

Chemical Property of Xerulin

Chemical Property:

• Vapor Pressure: 3.04E-09mmHg at 25°C
• Boiling Point: 476.5°Cat760mmHg
• Flash Point: 201.7°C
• PSA: 26.30000
• Density: 1.161g/cm³
• LogP: 3.23480
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 262.099379685
• Heavy Atom Count: 20
• Complexity: 653

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC#CC#CC=CC=CC=CC=C1C=CC(=O)O1
• Isomeric SMILES: C/C=C/C#CC#C/C=C/C=C/C=C/C=C\1/C=CC(=O)O1

Technology Process of Xerulin

There total 9 articles about Xerulin 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: 70.0%

(Z)-3-iodoprop-2-enoic acid (6214-35-3) + (3E,5E,7E,13E)-pentadeca-3,5,7,13-tetraene-1,9,11-triyne (259129-32-3) → xerulin (132971-61-0)

Guidance literature:

With copper(l) iodide; 2,6-di-tert-butyl-4-methyl-phenol; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; at 23 ℃; for 24h;

DOI:10.1021/ol990336h

Reference yield: 28.0%

all-trans-2,4,10-dodecatriene-6,8-diyn-1-al (17090-98-1) + [2-(5-oxo-5H-furan-2-ylidene)-ethyl]-triphenyl-phosphonium; bromide → (Z)-5-[(2Z,4E,6E,12E)-tetradecatetraene-8,10-diynylidene]-5H-2-furanone (132971-61-0) + xerulin (132971-61-0)

Guidance literature:

With potassium carbonate; In dichloromethane; at 50 ℃; Further Variations:; Reagents; Solvents; Temperatures; Product distribution;

DOI:10.1055/s-1999-3162

Reference yield: 28.0%

all-trans-2,4,10-dodecatriene-6,8-diyn-1-al (17090-98-1) + [2-(5-oxo-5H-furan-2-ylidene)-ethyl]-triphenyl-phosphonium; bromide → (Z)-5-[(2Z,4E,6E,12E)-tetradecatetraene-8,10-diynylidene]-5H-2-furanone (132971-61-0) + xerulin (132971-61-0)

Guidance literature:

With potassium carbonate; In dichloromethane; at 50 ℃; Further Variations:; Reagents; Solvents; Temperatures; Product distribution;

DOI:10.1055/s-1999-3162

upstream raw materials:

all-trans-2,4,10-dodecatriene-6,8-diyn-1-al

(Z)-3-iodoprop-2-enoic acid

(3E,5E,7E,13E)-pentadeca-3,5,7,13-tetraene-1,9,11-triyne

(5E)-hept-5-ene-1,3-diyne

Refernces

• 1、 Fiandanese, Vito,Bottalico, Daniela,Marchese, Giuseppe,Punzi, Angela. "New stereoselective methodology for the synthesis of dihydroxerulin and xerulin, potent inhibitors of the biosynthesis of cholesterol". . p. 11421 - 11425. Retrieved 2004.