CID 4484953

Base Information

• Chemical Name: CID 4484953
• CAS No.: 469-01-2
• Molecular Formula: C₁₇H₁₄O₆
• Molecular Weight: 314.295
• Wikidata: Q104252985
• Wikipedia: Pisatin
• Mol file: 469-01-2.mol

Synonyms:(+)-pisatin;(-)-pisatin;(S,S)-pisatin;pisatin;pisatin, (+)-;pisatin, (-)-;pisatin, (6aR-cis)-isomer;pisatin, (6aS-cis)-isomer

Chemical Property of CID 4484953

Chemical Property:

• Vapor Pressure: 3.87E-10mmHg at 25°C
• Boiling Point: 483°C at 760 mmHg
• Flash Point: 245.9°C
• PSA: 0.00000
• Density: 1.501g/cm³
• LogP: 2.15190
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 314.07903816
• Heavy Atom Count: 23
• Complexity: 472

Purity/Quality:

99% ^*data from raw suppliers

PISATIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)C3C(CO2)(C4=CC5=C(C=C4O3)OCO5)O

Technology Process of CID 4484953

There total 12 articles about CID 4484953 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: 89.0%

(3R,4S)-(+)-3-Hydroxy-3-<2-hydroxy-4,5-(methylenedioxy)phenyl>-7-methoxy-2,3-dihydro-4H-benzopyran-4-yl Trifluoromethanesulfonate (116888-63-2) → Pisatin (469-01-2)

Guidance literature:

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

Reference yield: 80.0%

dimethyl sulfate (77-78-1) + (+)-6a-hydroxymaackiain (14602-93-8,61218-44-8) → Pisatin (469-01-2)

Guidance literature:

With potassium carbonate; In acetone; for 0.5h; Heating;

DOI:10.1016/S0040-4039(98)00299-8

Reference yield:

5-Benzyloxy-2-[(Z)-2-(6-benzyloxy-benzo[1,3]dioxol-5-yl)-3-hydroxy-propenyl]-phenol → Pisatin (469-01-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / PPh₃, DEAD / benzene / 12 h / Ambient temperature

2: 90 percent / OsO₄, dihydroquinine, p-chlorobenzoate / CH₂Cl₂ / 24 h / -78 °C

3: 80 percent / hydrogen / 10percent Pd/C / methanol / 1.5 h

4: 80 percent / K₂CO₃ / acetone / 0.5 h / Heating

With osmium(VIII) oxide; hydrogen; potassium carbonate; triphenylphosphine; para-chlorobenzoic acid; diethylazodicarboxylate; dihydroquinine; palladium on activated charcoal; In methanol; dichloromethane; acetone; benzene;

DOI:10.1016/S0040-4039(98)00299-8

upstream raw materials:

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

dimethyl sulfate

(+)-6a-hydroxymaackiain

S-adenosyl-L-methionine

Downstream raw materials:

(+)-6a-hydroxymaackiain

Refernces

• 1、 Pinard, Emmanuel,Gaudry, Michel,Henot, Frederic,Thellend, Annie. "Asymmetric total synthesis of (+)-pisatin, a phytoalexin from garden peas (Pisum sativum L.)". . p. 2739 - 2742. Retrieved 2007/10/03.