pisatin

Base Information

• Chemical Name: pisatin
• CAS No.: 20186-22-5
• Molecular Formula: C₁₇H₁₄O₆
• Molecular Weight: 314.295
• Mol file: 20186-22-5.mol

Synonyms:6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-6a(12aH)-ol,3-methoxy-, (6aS-cis)- (8CI); (-)-Pisatin

Chemical Property of pisatin

Chemical Property:

• Vapor Pressure: 3.87E-10mmHg at 25°C
• Melting Point: 60-61 °C
• Boiling Point: 483°Cat760mmHg
• PKA: 11.91±0.20(Predicted)
• Flash Point: 245.9°C
• PSA: 66.38000
• Density: 1.501g/cm³
• LogP: 2.13760

Purity/Quality:

98%Min ^*data from raw suppliers

Pisatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of pisatin

There total 3 articles about pisatin 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: 93.0%

(3S,4R)-(-)-3-Hydroxy-3-<2-hydroxy-4,5-(methylenedioxy)phenyl>-7-methoxy-2,3-dihydro-4H-benzopyran-4-yl Trifluoromethanesulfonate (116888-64-3) → (-)-Pisatin (20186-22-5)

Guidance literature:

With sodium carbonate; at 100 ℃; for 5h;

Reference yield:

cis-3-<2-(tert-Butyldimethylsilyloxy)-4,5-(methylenedioxy)phenyl>-3-hydroxy-7-methoxy-2,3-dihydro-4H-benzopyran-4-yl (+)-Camphor-10-sulfonate (116888-59-6,116949-56-5) → (-)-Pisatin (20186-22-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 38 percent / Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran; pyridine / 1.) 1 h, 0 deg C, 2.) 24 h, room temperature

2: 80 percent / DMAP / CH₂Cl₂ / 1 h / -20 °C

3: 93 percent / 0.1 N Na₂CO₃ / 5 h / 100 °C

With dmap; tetrabutyl ammonium fluoride; sodium carbonate; In tetrahydrofuran; pyridine; dichloromethane;

Reference yield:

(3S,4R)-(-)-3-<2-Hydroxy-4,5-(methylenedioxy)phenyl>-7-methoxy-2,3-dihydro-4H-benzopyran-3,4-diol (116888-60-9) → (-)-Pisatin (20186-22-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / DMAP / CH₂Cl₂ / 1 h / -20 °C

2: 93 percent / 0.1 N Na₂CO₃ / 5 h / 100 °C

With dmap; sodium carbonate; In dichloromethane;

upstream raw materials:

(3S,4R)-(-)-3-Hydroxy-3-<2-hydroxy-4,5-(methylenedioxy)phenyl>-7-methoxy-2,3-dihydro-4H-benzopyran-4-yl Trifluoromethanesulfonate

cis-3-<2-(tert-Butyldimethylsilyloxy)-4,5-(methylenedioxy)phenyl>-3-hydroxy-7-methoxy-2,3-dihydro-4H-benzopyran-4-yl (+)-Camphor-10-sulfonate

(3S,4R)-(-)-3-<2-Hydroxy-4,5-(methylenedioxy)phenyl>-7-methoxy-2,3-dihydro-4H-benzopyran-3,4-diol

Refernces