130791-77-4

Basic information

• Product Name: (+)-huperzine A
• Synonyms: (+)-huperzine A
• CAS NO: 130791-77-4
• Molecular Weight: 242.321
• Mol File: 130791-77-4.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: (+)-huperzine A(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-huperzine A(130791-77-4)
• EPA Substance Registry System: (+)-huperzine A(130791-77-4)

Safety Data

• Hazardous Substances Data: 130791-77-4(Hazardous Substances Data)

Upstream product

• 92138-20-0 1-amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,10-trien-5-one 
• 207913-52-8 (1S,9S)-13-Eth-(E)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5,10-tetraene-1-carboxylic acid methyl ester 
• 134875-93-7 (1S,9S)-13-Eth-(Z)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5,10-tetraene-1-carboxylic acid methyl ester 
• 134875-94-8 (1S,9S)-13-Eth-(E)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5,10-tetraene-1-carboxylic acid 
• 120686-04-6 (1S,9S)-13-Eth-(Z)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5,10-tetraene-1-carboxylic acid 
• 134287-26-6 [(1S,9S)-13-Eth-(Z)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5,10-tetraen-1-yl]-methanol 
• 207913-51-7 (1R,9S)-10-Methanesulfonyloxy-5-methoxy-11-methyl-13-oxo-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-1-carboxylic acid methyl ester 
• 191600-72-3 (5R,9S)-methyl-8-hydroxy-2-methoxy-7-methyl-11-oxo-5,6,7,8,9,10-hexahydro-5,9-methanocycloocta[b]pyridine-5-carboxylate 
• 191600-74-5 (5R,9S)-methyl-2-methoxy-7-methyl-11-oxo-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridine-5-carboxylate 
• 185741-71-3 (1R,9R)-5-Methoxy-11-methylene-13-oxo-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-1-carboxylic acid methyl ester 
• 134875-95-9 [(1S,9S)-13-Eth-(E)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5,10-tetraen-1-yl]-carbamic acid methyl ester 
• 120686-05-7 (E)-(+/-)-(11-ethylidene-9,10-dihydro-2-methoxy-7-methyl-5,9-methanocyclooctapyridin-5(6H)-yl)carbamic acid methyl ester 
• 123436-03-3 (5R,9R,11E)-5-(ethoxycarbonylamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one 

Downstream Products

• 3279-76-3 6-methyl-2(1H)-pyridone 
• 955117-18-7 (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one 
• 92138-20-0 natural Huperzine A 
• 130791-77-4 (+)-huperzine A 

Relevant articles and documents

Synthetic method of huperzine A

The invention belongs to the technical field of medicine synthesis and particularly relates to a synthetic method of huperzine A. The method includes twelve steps of reactions, 1,4-dioxaspiro[4.5]decan-8-one being a raw material, so that the chemical synthesis of the huperzine A is completed at a high total yield. The method is fewer in reaction steps, is simple in operations, has high yield, is stable in intermediates and gentle in reaction conditions, and is easy to control in reactions.

PREPARATION OF (-)-HUPERZINE A

The present invention relates to a method for preparing (?)-huperzine A. The method involves: allowing a mixture of (±)-huperzine A obtained from chemical synthesis and a chiral acid to form (±)-huperzine A chiral acid salt under suitable conditions; recrystallizing the chiral acid salt from an organic solvent and basifying with an alkali to obtain optically pure (?)-huperzine A. The method is convenient to operate and suitable for industrial production. The chemical purity and optical purity of (?)-huperzine A obtained by the method are each greater than 99.5%, satisfying the requirement for raw pharmaceutical purity in the pharmaceutical industry.

An efficient total synthesis of (-)-huperzine A

The total synthesis of Lycopodium alkaloid (-)-huperzine A has been accomplished in 10 steps with 17% overall yield from commercially abundant (R)-pulegone. The synthetic route features an efficient synthesis of 4 via a Buchwald-Hartwig coupling reaction,