Huperzine

Base Information

• Chemical Name: Huperzine
• CAS No.: 116-28-9
• Molecular Formula: C15H18N2O
• Molecular Weight: 242.32
• Mol file: 116-28-9.mol

Synonyms:Huperzia Serrata Extract;Selagnine;

Chemical Property of Huperzine

Chemical Property:

• Appearance/Colour: Brown to white powder
• Vapor Pressure: 3.73E-10mmHg at 25°C
• Refractive Index: 1.626
• Boiling Point: 500.6 °C at 760 mmHg
• Flash Point: 256.6 °C
• PSA: 58.88000
• Density: 1.2 g/cm³
• LogP: 2.69780

Purity/Quality:

98%,99%, ^*data from raw suppliers

HUPERIZNE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Huperzine

There total 124 articles about Huperzine 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: 80.0%

methyl ((5S,E)-11-ethylidene-2-methoxy-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-5-yl)carbamate (185741-46-2) → natural Huperzine A (92138-20-0,102518-79-6,103735-86-0,120786-18-7,130791-77-4,132435-40-6,116-28-9)

Guidance literature:

methyl ((5S,E)-11-ethylidene-2-methoxy-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-5-yl)carbamate; With trimethylsilyl iodide; In chloroform; for 6h; Reflux; Inert atmosphere;

With methanol; In chloroform; for 3h; Reflux; Inert atmosphere;

DOI:10.1021/ol9022408

Reference yield: 74.0%

(-)-huperzine A 2,3-dibenzoyl-D-tartaric acid salt → natural Huperzine A (92138-20-0,102518-79-6,103735-86-0,120786-18-7,130791-77-4,132435-40-6,116-28-9)

Guidance literature:

With sodium hydroxide; In water; for 1h; pH=9 - 9.3;

Reference yield: 60.0%

C16H16N2O2 → natural Huperzine A (92138-20-0,102518-79-6,103735-86-0,120786-18-7,130791-77-4,132435-40-6,116-28-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 80 ℃; for 36h;

upstream raw materials:

(E)-(+/-)-(11-ethylidene-9,10-dihydro-2-methoxy-7-methyl-5,9-methanocyclooctapyridin-5(6H)-yl)carbamic acid methyl ester

[13-Eth-(E)-ylidene-5-methoxy-11-methylene-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-trien-1-yl]-carbamic acid methyl ester

(E)-11-ethylidene-5,6,9,10-tetrahydro-5-(methoxycarbonylamino)-7-methyl-5,9-methano-1H-cycloocta[b]pyridin-2-one

13-Eth-(E)-ylidene-5-methoxy-11-methylene-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-1-carboxylic acid

Refernces

• 1、 Tudhope, Stephen R.,Bellamy, Julie A.,Ball, Anthony,Rajasekar, Dewakar,Azadi-Ardakani, Manouchehr,Meera, Harihara Subramanian,Gnanadeepam, Jesudoss Mercy,Saiganesh, Ramanathan,Gibson, Frank,He, Linli,Behrens, Carl H.,Underiner, Gail,Marfurt, Judith,Favre, Nathalie. "Development of a large-scale synthetic route to manufacture (-)-huperzine A". . p. 635 - 642. Retrieved 2012.
• 2、 Camps, Pelayo,Contreras, Joan,El Achab, Rachid,Morral, Jordi,Mu?oz-Torrero, Diego,Font-Bardia, Mercè,Solans, Xavier,Badia, Albert,Vivas, Nuria M.. "New syntheses of rac-Huperzine A and its rac-7-ethyl-derivative. Evaluation of several Huperzine A analogues as acetylcholinesterase inhibitors". . p. 4541 - 4553. Retrieved 2000.
• 3、 -. "METHODS OF RESOLVING RACEMIC MIXTURE TO OBTAIN (-)-HUPERZINE A". Page/Page column 10. . Retrieved 2016/04/26.
• 4、 White, James D.,Li, Yang,Kim, Jungchul,Terinek, Miroslav. "Cyclobutane Synthesis and Fragmentation. A Cascade Route to the Lycopodium Alkaloid (-)-Huperzine A". . p. 11806 - 11817. Retrieved 2015/12/11.