cis-Moschamine

Base Information

• Chemical Name: cis-Moschamine
• CAS No.: 193224-24-7
• Molecular Formula: C20H20N2O4
• Molecular Weight: 352.38400
• Mol file: 193224-24-7.mol

Synonyms:2-Propenamide, N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-, (2Z)-;(Z)-Moschamine;2-Propenamide, N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-, (Z)-;(2Z)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide;

Chemical Property of cis-Moschamine

Chemical Property:

• PSA: 94.58000
• LogP: 3.35070

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

cis-Moschamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-Moschamine

There total 11 articles about cis-Moschamine 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: 99.0%

3-(2-aminoethyl)-1H-indol-5-ol (50-67-9) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) → (2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide (68573-23-9,193224-24-7)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide;

DOI:10.3987/COM-98-8156

Reference yield: 96.1%

3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + serotonin hydrochloride (153-98-0,21591-86-6) → N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)acrylamide (193224-24-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.02.028

Reference yield: 69.2%

→ (2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide (68573-23-9,193224-24-7)

Guidance literature:

upstream raw materials:

3-(2-aminoethyl)-1H-indol-5-ol

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

(E)-N-[2-(1-Hydroxy-1H-indol-3-yl)-ethyl]-3-(4-hydroxy-3-methoxy-phenyl)-acrylamide

serotonin hydrochloride

Downstream raw materials:

N-feruloylserotonin diacetate

Refernces

• 1、 Park, Jae B.. "Synthesis, biological activities and bioavailability of moschamine, a safflomide-type phenylpropenoic acid amide found in Centaurea cyanus". . p. 1465 - 1472. Retrieved 2012.
• 2、 Takao, Koichi,Toda, Kazuhiro,Saito, Takayuki,Sugita, Yoshiaki. "Synthesis of amide and ester derivatives of cinnamic acid and its analogs: Evaluation of their free radical scavenging and monoamine oxidase and cholinesterase inhibitory activities". . p. 1020 - 1027. Retrieved 2017/11/17.
• 3、 Hu, Weimin,Qin, Hua,Cui, Yuxin,Jia, Yanxing. "Total synthesis of (+)- and (-)-decursivine and (±)-serotobenine through a cascade witkop photocyclization/elimination/addition sequence: Scope and mechanistic insights". supporting information. p. 3139 - 3147. Retrieved 2013/03/28.