N-caffeoyl serotonin

Base Information

• Chemical Name: N-caffeoyl serotonin
• CAS No.: 1190305-14-6
• Molecular Formula: C₁₉H₁₈N₂O₄
• Molecular Weight: 338.363
• Mol file: 1190305-14-6.mol

Synonyms:N-caffeoyl serotonin

Chemical Property of N-caffeoyl serotonin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-caffeoyl serotonin

There total 5 articles about N-caffeoyl serotonin 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: 83.3%

C25H26N2O4 → N-caffeoyl serotonin (1190305-14-6)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2011.02.028

Reference yield: 54.0%

→ N-caffeoyl serotonin (1190305-14-6)

Guidance literature:

Reference yield:

3-(3,4-bis-allyloxyphenyl)acrylic acid (200059-78-5) → N-caffeoyl serotonin (1190305-14-6)

Guidance literature:

Multi-step reaction with 2 steps

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane; N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

2: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 12 h / 20 °C

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.02.028

upstream raw materials:

3-(3,4-bis-allyloxyphenyl)acrylic acid

3,4-diallyloxybenzaldehyde

3,4-dihydroxybenzaldehyde

Downstream raw materials:

C₁₉H₂₀N₂O₄

Refernces

• 1、 Takahashi, Toshiyuki,Miyazawa, Mitsuo. "Synthesis and structure-activity relationships of serotonin derivatives effect on α-glucosidase inhibition". . p. 1762 - 1770. Retrieved 2012/11/14.
• 2、 Takahashi,Miyazawa, Mitsuo. "Serotonin derivatives as inhibitors of β-secretase (BACE 1)". experimental part. p. 301 - 305. Retrieved 2012/01/02.