(4E,6E)-7-(4-(benzyloxy)phenyl)-1-(3-bromo-4-isopropoxyphenyl)hepta-4,6-dien-3-one

Base Information

• Chemical Name: (4E,6E)-7-(4-(benzyloxy)phenyl)-1-(3-bromo-4-isopropoxyphenyl)hepta-4,6-dien-3-one
• CAS No.: 1390642-42-8
• Molecular Formula: C₂₉H₂₉BrO₃
• Molecular Weight: 505.451

Synonyms:(4E,6E)-7-(4-(benzyloxy)phenyl)-1-(3-bromo-4-isopropoxyphenyl)hepta-4,6-dien-3-one

Chemical Property of (4E,6E)-7-(4-(benzyloxy)phenyl)-1-(3-bromo-4-isopropoxyphenyl)hepta-4,6-dien-3-one

Chemical Property:

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Technology Process of (4E,6E)-7-(4-(benzyloxy)phenyl)-1-(3-bromo-4-isopropoxyphenyl)hepta-4,6-dien-3-one

There total 2 articles about (4E,6E)-7-(4-(benzyloxy)phenyl)-1-(3-bromo-4-isopropoxyphenyl)hepta-4,6-dien-3-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: 82.0%

benzyl coumaraldehyde (60960-89-6) + dimethyl (4-(3-bromo-4-isopropoxyphenyl)-2-oxobutyl)phosphonate (1390642-34-8) → (4E,6E)-7-(4-(benzyloxy)phenyl)-1-(3-bromo-4-isopropoxyphenyl)hepta-4,6-dien-3-one (1390642-42-8)

Guidance literature:

dimethyl (4-(3-bromo-4-isopropoxyphenyl)-2-oxobutyl)phosphonate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 0.166667h; Inert atmosphere;

benzyl coumaraldehyde; at 50 - 60 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ol301893t

Reference yield:

3-(3-bromo-4-isopropoxy-phenyl)propionic acid methyl ester (594858-52-3) → (4E,6E)-7-(4-(benzyloxy)phenyl)-1-(3-bromo-4-isopropoxyphenyl)hepta-4,6-dien-3-one (1390642-42-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methyllithium / tetrahydrofuran; diethyl ether / 0.5 h / Inert atmosphere

1.2: 2.25 h / 20 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.17 h / Inert atmosphere

2.2: 24 h / 50 - 60 °C / Inert atmosphere

With methyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ol301893t

Reference yield: 98.0%

(4E,6E)-7-(4-(benzyloxy)phenyl)-1-(3-bromo-4-isopropoxyphenyl)hepta-4,6-dien-3-one (1390642-42-8) → 1-(3-bromo-4-isopropoxyphenyl)-7-(4-hydroxyphenyl)heptan-3-one (1390642-50-8)

Guidance literature:

With 20 % Pd(OH)2/C; hydrogen; In water; ethyl acetate; for 2h; Inert atmosphere;

DOI:10.1021/ol301893t

upstream raw materials:

benzyl coumaraldehyde

dimethyl (4-(3-bromo-4-isopropoxyphenyl)-2-oxobutyl)phosphonate

3-(3-bromo-4-isopropoxy-phenyl)propionic acid methyl ester

Downstream raw materials:

1-(3-bromo-4-isopropoxyphenyl)-7-(4-hydroxyphenyl)heptan-3-one

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