3-(3-Hydroxy-5-oxo-4-phenyl-2,5-dihydrofuran-2-ylidene)benzofuran-2(3H)-one

Base Information

• Chemical Name: 3-(3-Hydroxy-5-oxo-4-phenyl-2,5-dihydrofuran-2-ylidene)benzofuran-2(3H)-one
• CAS No.: 10091-92-6
• Molecular Formula: C₁₈H₁₀O₅
• Molecular Weight: 306.274
• Mol file: 10091-92-6.mol

Synonyms:2(3H)-Benzofuranone,3-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furylidene)- (8CI); Calycin (6CI,7CI);Calycine

Chemical Property of 3-(3-Hydroxy-5-oxo-4-phenyl-2,5-dihydrofuran-2-ylidene)benzofuran-2(3H)-one

Chemical Property:

• Vapor Pressure: 2.73E-13mmHg at 25°C
• Boiling Point: 558.1°C at 760 mmHg
• Flash Point: 212.1°C
• PSA: 72.83000
• Density: 1.564g/cm³
• LogP: 2.84280

Purity/Quality:

98%,99%, ^*data from raw suppliers

CALYCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(3-Hydroxy-5-oxo-4-phenyl-2,5-dihydrofuran-2-ylidene)benzofuran-2(3H)-one

There total 9 articles about 3-(3-Hydroxy-5-oxo-4-phenyl-2,5-dihydrofuran-2-ylidene)benzofuran-2(3H)-one 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: 33.0%

(3-methoxy-5-oxo-4-phenyl-5H-furan-2-ylidene)-(2-methoxy-phenyl)-acetic acid methyl ester (6200-02-8) → isocalycine + calycine (10091-92-6,15222-44-3)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 ℃; for 6h;

DOI:10.1002/ejoc.200500142

Reference yield:

methanol (67-56-1) + Pulvinic acid lacton (6273-79-6) → calycine (10091-92-6,15222-44-3) + vulpic acid (521-52-8,73622-57-8)

Guidance literature:

DOI:10.1080/14786410802682536

Reference yield:

4-methoxy-2-(2-methoxy-phenyl)-3-oxo-butyric acid methyl ester (866556-32-3) → calycine (10091-92-6,15222-44-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 95 percent / triethylamine / benzene / 72 h

2.1: LDA / tetrahydrofuran / 1 h / -78 °C

2.2: 97 percent / tetrahydrofuran / 12 h / 20 °C

3.1: 63 percent / Me₃SiOTf / CH₂Cl₂ / 14 h / -78 - 20 °C

4.1: 53 percent / pyridine / CH₂Cl₂ / 4 h / -78 - -10 °C

5.1: 92 percent / K₃PO₄; [Pd(PPh₃)4] / dioxane / 4 h / Heating

6.1: 33 percent / BBr₃ / CH₂Cl₂ / 6 h / 0 °C

With pyridine; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; boron tribromide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; benzene; 5.1: Suzuki reaction;

DOI:10.1002/ejoc.200500142

upstream raw materials:

(3-methoxy-5-oxo-4-phenyl-5H-furan-2-ylidene)-(2-methoxy-phenyl)-acetic acid methyl ester

4-methoxy-2-(2-methoxy-phenyl)-3-oxo-butyric acid methyl ester

(Z)-4-Methoxy-2-(2-methoxy-phenyl)-3-trimethylsilanyloxy-but-2-enoic acid methyl ester

1-Methoxy-2-{(Z)-3-methoxy-1-[1-methoxy-1-trimethylsilanyloxy-meth-(Z)-ylidene]-2-trimethylsilanyloxy-allyl}-benzene

Refernces

• 1、 Ahmed, Zafar,Albrecht, Uwe,Langer, Peter. "Synthesis of leprapinic acid, calycine and analogues by sequential "[3+2] cyclization/suzuki/lactonization" reactions". . p. 3469 - 3474. Retrieved 2007/10/03.