ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-acetamidopropoxy)cinnamate

Base Information

Chemical Name:ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-acetamidopropoxy)cinnamate
CAS No.:540779-42-8
Molecular Formula:C₃₂H₃₉NO₅
Molecular Weight:517.665
Hs Code.:

Synonyms:ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-acetamidopropoxy)cinnamate

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Chemical Property of ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-acetamidopropoxy)cinnamate

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Technology Process of ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-acetamidopropoxy)cinnamate

There total 12 articles about ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-acetamidopropoxy)cinnamate 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: 77.0%

: 540779-41-7
ethyl (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-(3'-acetamidopropoxy)cinnamate

: 540779-42-8
ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-acetamidopropoxy)cinnamate

Guidance literature:: With boron tribromide; In dichloromethane; at -78 ℃; for 2h;
DOI:10.1021/jm030524k

Reference yield:

: 7781-98-8
ethyl-3-hydroxybenzoate

: 540779-42-8
ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-acetamidopropoxy)cinnamate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 53 percent / Br₂; AcOH / 20 h / 20 °C

2.1: 84 percent / K₂CO₃ / acetone / 15 h / Heating

3.1: 91 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

4.1: PCC / CH₂Cl₂ / 5 h / 20 °C

5.1: KN(SiMe₃)2 / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C

5.2: 0.28 g / diethyl ether; tetrahydrofuran / -78 - 20 °C

6.1: 92 percent / BBr₃ / CH₂Cl₂ / 2 h / -78 °C

7.1: 81 percent / K₂CO₃ / acetone / 20 h / Heating

8.1: 83 percent / Pd(PPh₃)4; aq. Na₂CO₃ / 1,2-dimethoxy-ethane / 20 h / Heating

9.1: aq. HCl / ethanol / 1 h / Heating

10.1: 280 mg / pyridine / CH₂Cl₂ / 20 °C

11.1: 77 percent / BBr₃ / CH₂Cl₂ / 2 h / -78 °C

With pyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromine; boron tribromide; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; acetone;
DOI:10.1021/jm030524k

Reference yield:

: 33141-66-1
ethyl 4-bromo-3-hydroxybenzoate

: 540779-42-8
ethyl (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-(3'-acetamidopropoxy)cinnamate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 84 percent / K₂CO₃ / acetone / 15 h / Heating

2.1: 91 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

3.1: PCC / CH₂Cl₂ / 5 h / 20 °C

4.1: KN(SiMe₃)2 / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C

4.2: 0.28 g / diethyl ether; tetrahydrofuran / -78 - 20 °C

5.1: 92 percent / BBr₃ / CH₂Cl₂ / 2 h / -78 °C

6.1: 81 percent / K₂CO₃ / acetone / 20 h / Heating

7.1: 83 percent / Pd(PPh₃)4; aq. Na₂CO₃ / 1,2-dimethoxy-ethane / 20 h / Heating

8.1: aq. HCl / ethanol / 1 h / Heating

9.1: 280 mg / pyridine / CH₂Cl₂ / 20 °C

10.1: 77 percent / BBr₃ / CH₂Cl₂ / 2 h / -78 °C

With pyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron tribromide; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; pyridinium chlorochromate; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; acetone;
DOI:10.1021/jm030524k