5,7-Dihydroxy-2,2-dimethyl-10-(3-methyl-2-butenyl)-8-phenyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one

Base Information

• Chemical Name: 5,7-Dihydroxy-2,2-dimethyl-10-(3-methyl-2-butenyl)-8-phenyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one
• CAS No.: 42438-75-5
• Molecular Formula: C25H24O5
• Molecular Weight: 404.463
• Mol file: 42438-75-5.mol

Synonyms:3,5-Dihydroxy-8,8-dimethyl-10-(3-methyl-but-2-enyl)-2-phenyl-8H-pyrano[3,2-g]chromen-4-one;Sericetin;

Chemical Property of 5,7-Dihydroxy-2,2-dimethyl-10-(3-methyl-2-butenyl)-8-phenyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one

Chemical Property:

• Vapor Pressure: 2.05E-15mmHg at 25°C
• Boiling Point: 603.5°C at 760 mmHg
• Flash Point: 207.5°C
• PSA: 79.90000
• Density: 1.271g/cm³
• LogP: 5.56410

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5,7-Dihydroxy-2,2-dimethyl-10-(3-methyl-2-butenyl)-8-phenyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one

There total 11 articles about 5,7-Dihydroxy-2,2-dimethyl-10-(3-methyl-2-butenyl)-8-phenyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-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: 88.0%

C32H30O5 → sericetin (42438-75-5)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jnatprod.8b00434

Reference yield:

3-(benzyloxy)-5,7-dihydroxy-2-phenyl-4H-chromen-4-one (1616279-97-0) → sericetin (42438-75-5)

Guidance literature:

Multi-step reaction with 4 steps

1: calcium hydroxide / methanol / 58 h / 20 °C / Inert atmosphere

2: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere

3: diethylaniline / 4 h / 270 °C / Inert atmosphere

4: boron trichloride / dichloromethane / 2 h / -78 °C / Inert atmosphere

With boron trichloride; potassium carbonate; calcium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; 3: |Claisen Rearrangement;

DOI:10.1021/acs.jnatprod.8b00434

Reference yield:

3,3-dimethyl acrylaldehyde (107-86-8) → sericetin (42438-75-5)

Guidance literature:

Multi-step reaction with 4 steps

1: calcium hydroxide / methanol / 58 h / 20 °C / Inert atmosphere

2: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere

3: diethylaniline / 4 h / 270 °C / Inert atmosphere

4: boron trichloride / dichloromethane / 2 h / -78 °C / Inert atmosphere

With boron trichloride; potassium carbonate; calcium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; 3: |Claisen Rearrangement;

DOI:10.1021/acs.jnatprod.8b00434

upstream raw materials:

3-(benzyloxy)-5,7-dihydroxy-2-phenyl-4H-chromen-4-one

3,3-dimethyl acrylaldehyde

Refernces

• 1、 Kim, Eun-Sun,Jang, Hongjun,Chang, Sun-Young,Baek, Seung-Hoon,Bae, Ok-Nam,Kim, Hyoungsu. "Total Synthesis and Biological Evaluation of Sericetin for Protection against Cisplatin-Induced Acute Kidney Injury". . p. 2647 - 2653. Retrieved 2019/01/04.