(E)-5-(3,7-dimethyl-5-oxoocta-2,6-dien-1-yl)-4-hydroxy-6-methoxy-2-phenethylisoindolin-1-one

Base Information

• Chemical Name: (E)-5-(3,7-dimethyl-5-oxoocta-2,6-dien-1-yl)-4-hydroxy-6-methoxy-2-phenethylisoindolin-1-one
• CAS No.: 1416052-89-5
• Molecular Formula: C₂₇H₃₁NO₄
• Molecular Weight: 433.547

Synonyms:(E)-5-(3,7-dimethyl-5-oxoocta-2,6-dien-1-yl)-4-hydroxy-6-methoxy-2-phenethylisoindolin-1-one

Chemical Property of (E)-5-(3,7-dimethyl-5-oxoocta-2,6-dien-1-yl)-4-hydroxy-6-methoxy-2-phenethylisoindolin-1-one

Chemical Property:

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-(3,7-dimethyl-5-oxoocta-2,6-dien-1-yl)-4-hydroxy-6-methoxy-2-phenethylisoindolin-1-one

There total 22 articles about (E)-5-(3,7-dimethyl-5-oxoocta-2,6-dien-1-yl)-4-hydroxy-6-methoxy-2-phenethylisoindolin-1-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: 61.0%

(E)-5-(3,7-dimethyl-5-oxoocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one (1610729-80-0) → (E)-5-(3,7-dimethyl-5-oxoocta-2,6-dien-1-yl)-4-hydroxy-6-methoxy-2-phenethylisoindolin-1-one (1416052-89-5)

Guidance literature:

(E)-5-(3,7-dimethyl-5-oxoocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one; With dimethylboron bromide; 1-penten; In dichloromethane; at -78 ℃; for 3h;

With triethylamine; In dichloromethane-d2; at 0 - 20 ℃; for 6h;

DOI:10.1021/jo500795z

Reference yield:

(E)-5-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one (1610729-78-6) → (E)-5-(3,7-dimethyl-5-oxoocta-2,6-dien-1-yl)-4-hydroxy-6-methoxy-2-phenethylisoindolin-1-one (1416052-89-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / 40 °C

2.1: trans-bis(triphenylphosphine)palladium dichloride; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl / dichloromethane / 7 h / 20 °C

3.1: 1-penten; dimethylboron bromide / dichloromethane / 3 h / -78 °C

3.2: 6 h / 0 - 20 °C

With trans-bis(triphenylphosphine)palladium dichloride; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; dimethylboron bromide; 1-penten; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo500795z

Reference yield:

(E)-5-(5-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one (1610729-79-7) → (E)-5-(3,7-dimethyl-5-oxoocta-2,6-dien-1-yl)-4-hydroxy-6-methoxy-2-phenethylisoindolin-1-one (1416052-89-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trans-bis(triphenylphosphine)palladium dichloride; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl / dichloromethane / 7 h / 20 °C

2.1: 1-penten; dimethylboron bromide / dichloromethane / 3 h / -78 °C

2.2: 6 h / 0 - 20 °C

With trans-bis(triphenylphosphine)palladium dichloride; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; dimethylboron bromide; 1-penten; In dichloromethane;

DOI:10.1021/jo500795z

upstream raw materials:

(E)-5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-ol

(E)-6-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-5-methoxy-7-(methoxymethoxy)isobenzofuran-1(3H)-one

C₂₇H₄₆O₆Si

(E)-5-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)isobenzofuran-1(3H)-one

Refernces

Total Synthesis of Isohericerin, Isohericenone, and Erinacerin A: Development of a Copper-Catalyzed Methylboronation of Terminal Alkynes

10.1021/acs.joc.7b00920

This research details the efficient and concise total syntheses of three bioactive natural products: isohericerin, isohericenone, and erinacerin A. The study's purpose was to develop straightforward synthetic routes for these compounds, which exhibit significant inhibitory activity against the proliferation of SK-MEL-2 cells, making them potential candidates for anti-cancer drug discovery. The key reactions in the synthesis process included a Mannich reaction with commercially available hydroxybenzoate, a Suzuki-Miyaura coupling reaction to connect geranyl side chains to the isoindolinone core, and a highly regioselective and efficient method for the Cu-catalyzed methylboronation of functionalized terminal alkynes to synthesize the C5’-oxidized geranyl side unit of isohericenone. The researchers successfully synthesized the common isoindolinone core in three steps and developed a mild and selective methylboronation reaction of terminal alkynes with B2(pin)2 and methyl iodide promoted by an NHC-Cu catalyst. The synthesis involved a variety of chemicals, including hydroxybenzoate, phenethylamine, formaldehyde, various terminal alkynes, bis(pinacolato)diboron, methyl iodide, and several NHC-Cu complexes. The conclusions of the research emphasized the successful synthesis of the target compounds with improved yields and efficiency, and the potential for future evaluation of their biological activities.

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