ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-aminocinnamate

Base Information

• Chemical Name: ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-aminocinnamate
• CAS No.: 1352042-75-1
• Molecular Formula: C₂₇H₃₁NO₃
• Molecular Weight: 417.548
• Mol file: 1352042-75-1.mol

Synonyms:ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-aminocinnamate

Chemical Property of ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-aminocinnamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-aminocinnamate

There total 4 articles about ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-aminocinnamate 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: 81.0%

ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-aminocinnamate (1352042-73-9) → ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-aminocinnamate (1352042-75-1)

Guidance literature:

ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-aminocinnamate; With boron tribromide; In dichloromethane; at -78 ℃; for 2.5h; Inert atmosphere;

With water; In dichloromethane; Inert atmosphere;

DOI:10.1021/jm2011436

Reference yield:

ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-nitrocinnamate (1352042-59-1) → ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-aminocinnamate (1352042-75-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tin(II) chloride hydrate / ethanol / 2 h / 80 °C / Inert atmosphere

2.1: boron tribromide / dichloromethane / 2.5 h / -78 °C / Inert atmosphere

2.2: Inert atmosphere

With tin(II) chloride hydrate; boron tribromide; In ethanol; dichloromethane;

DOI:10.1021/jm2011436

Reference yield:

4-bromo-3-nitrobenzaldehyde (163596-75-6) → ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-aminocinnamate (1352042-75-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene / 18.5 h / Reflux; Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane / 16 h / Reflux; Inert atmosphere

3.1: tin(II) chloride hydrate / ethanol / 2 h / 80 °C / Inert atmosphere

4.1: boron tribromide / dichloromethane / 2.5 h / -78 °C / Inert atmosphere

4.2: Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tin(II) chloride hydrate; boron tribromide; sodium carbonate; In 1,2-dimethoxyethane; ethanol; dichloromethane; toluene; 1.1: Wittig reaction / 2.1: Suzuki-Miyaura coupling;

DOI:10.1021/jm2011436

upstream raw materials:

ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-nitrocinnamate

ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-aminocinnamate

4-bromo-3-nitrobenzaldehyde

(E)-ethyl 3-(4-bromo-3-nitrophenyl)acrylate

Downstream raw materials:

(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-aminocinnamic acid

ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-azidocinnamate

(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-azidocinnamic acid