4β-[6-(4-[(E)-3-(2,4-dimethyl-3-quinolyl)-3-oxo-1-propenyl]-2-methoxyphenoxy)hexanamido]-4-deoxypodophyllotoxin

Base Information

• Chemical Name: 4β-[6-(4-[(E)-3-(2,4-dimethyl-3-quinolyl)-3-oxo-1-propenyl]-2-methoxyphenoxy)hexanamido]-4-deoxypodophyllotoxin
• CAS No.: 1357098-95-3
• Molecular Formula: C₄₉H₅₀N₂O₁₁
• Molecular Weight: 842.943

Synonyms:4β-[6-(4-[(E)-3-(2,4-dimethyl-3-quinolyl)-3-oxo-1-propenyl]-2-methoxyphenoxy)hexanamido]-4-deoxypodophyllotoxin

Chemical Property of 4β-[6-(4-[(E)-3-(2,4-dimethyl-3-quinolyl)-3-oxo-1-propenyl]-2-methoxyphenoxy)hexanamido]-4-deoxypodophyllotoxin

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Technology Process of 4β-[6-(4-[(E)-3-(2,4-dimethyl-3-quinolyl)-3-oxo-1-propenyl]-2-methoxyphenoxy)hexanamido]-4-deoxypodophyllotoxin

There total 6 articles about 4β-[6-(4-[(E)-3-(2,4-dimethyl-3-quinolyl)-3-oxo-1-propenyl]-2-methoxyphenoxy)hexanamido]-4-deoxypodophyllotoxin 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: 69.0%

(E)-1-(2,4-dimethyl-3-quinolyl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one (1186612-87-2) + 4β-[6-bromohexanamido]-4-deoxypodophyllotoxin (1357098-88-4) → 4β-[6-(4-[(E)-3-(2,4-dimethyl-3-quinolyl)-3-oxo-1-propenyl]-2-methoxyphenoxy)hexanamido]-4-deoxypodophyllotoxin (1357098-95-3)

Guidance literature:

With potassium carbonate; In acetone; for 18h; Reflux;

DOI:10.1016/j.ejmech.2011.11.024

Reference yield:

1-(2,4-dimethyl-quinolin-3-yl)-ethanone (14428-41-2) → 4β-[6-(4-[(E)-3-(2,4-dimethyl-3-quinolyl)-3-oxo-1-propenyl]-2-methoxyphenoxy)hexanamido]-4-deoxypodophyllotoxin (1357098-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / ethanol; water / 12 h / Reflux

2: potassium carbonate / acetone / 18 h / Reflux

With potassium carbonate; potassium hydroxide; In ethanol; water; acetone; 1: Claisen-Schmidt condensation;

DOI:10.1016/j.ejmech.2011.11.024

Reference yield:

6-bromohexanoyl chloride (22809-37-6) → 4β-[6-(4-[(E)-3-(2,4-dimethyl-3-quinolyl)-3-oxo-1-propenyl]-2-methoxyphenoxy)hexanamido]-4-deoxypodophyllotoxin (1357098-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 0 - 20 °C

2: potassium carbonate / acetone / 18 h / Reflux

With potassium carbonate; triethylamine; In dichloromethane; acetone;

DOI:10.1016/j.ejmech.2011.11.024

upstream raw materials:

(E)-1-(2,4-dimethyl-3-quinolyl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one

4β-[6-bromohexanamido]-4-deoxypodophyllotoxin

1-(2,4-dimethyl-quinolin-3-yl)-ethanone

6-bromohexanoyl chloride

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