120686-08-0

Basic information

• Product Name: Spiro[1,3-dioxolane-2,6'(2'H)-quinolin]-2'-one, 1',5',7',8'-tetrahydro-
• Synonyms: Spiro[1,3-dioxolane-2,6'(2'H)-quinolin]-2'-one, 1',5',7',8'-tetrahydro-;7,8-dihydro-1H-spiro[[1,3]dioxolane-2,6-quinolin]-2(5H)-one
• CAS NO: 120686-08-0
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.23
• Mol File: 120686-08-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 250 °C (decomp)
• Boiling Point: 493.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.30±0.1 g/cm3(Predicted)
• PKA: 12.91±0.20(Predicted)
• CAS DataBase Reference: Spiro[1,3-dioxolane-2,6'(2'H)-quinolin]-2'-one, 1',5',7',8'-tetrahydro-(CAS DataBase Reference)
• NIST Chemistry Reference: Spiro[1,3-dioxolane-2,6'(2'H)-quinolin]-2'-one, 1',5',7',8'-tetrahydro-(120686-08-0)
• EPA Substance Registry System: Spiro[1,3-dioxolane-2,6'(2'H)-quinolin]-2'-one, 1',5',7',8'-tetrahydro-(120686-08-0)

Safety Data

• Hazardous Substances Data: 120686-08-0(Hazardous Substances Data)

Upstream product

• 57440-57-0 1-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyrrolidine 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 105-37-3 Ethyl propionate 
• 922-67-8 propynoic acid methyl ester 
• 120685-98-5 1',5',7',8'-tetrahydro-1'-(phenylmethyl)spiro<1,3-dioxolane-2,6'(2'H)-quinolin>-2'-one 
• 128562-36-7 7-((dimethylamino)methyl)-1,4-dioxaspiro[4.5]decan-8-one 
• 41220-29-5 N-carbamoylmethylpyridinium chloride 
• 16490-68-9 2-chloroacrylamide 
• 3510-44-9 methyl cis-2-chloroacrylate 
• 285139-08-4 7-((dimethylamino)methylene)-1,4-dioxaspiro[4.5]decane-8-one 
• 144810-01-5 1,4-cyclohexanedione-1-ethylene acetal 4-trimethylsilyl enol ether 

Downstream Products

• 167557-60-0 7',8'-dihydrospiro<1,3-dioxolane-2,6'(5'H)-quinolin>-2'-yl 4-methylbenzenesulfonate 
• 167557-63-3 2-Benzylamino-7,8-dihydro-5H-quinolin-6-one 
• 167557-61-1 7',8'-dihydro-N-(phenylmethyl)spiro<1,3-dioxolane-2,6'(5'H)-quinolin>-2'-amine 
• 167557-64-4 N²-Benzyl-N⁶-propyl-5,6,7,8-tetrahydro-quinoline-2,6-diamine 
• 167557-62-2 N²-benzyl-N⁶,N⁶-dipropyl-5,6,7,8-tetrahydroquinoline-2,6-diamine 
• 167557-65-5 N-(2-Benzylamino-5,6,7,8-tetrahydro-quinolin-6-yl)-N-propyl-propionamide 
• 116-28-9 (-)-huperzine A 
• 120786-18-7 (+/-)-huperzine 
• 123435-97-2 5,6,7,8-tetrahydro-2-methoxy-6-oxo-5-quinolinecarboxylic acid methyl ester 
• 120686-09-1 2-methoxy-6-oxo-5,6,7,8-tetrahydroquinoline 

Relevant articles and documents

Synthesis of a hybrid analog of the acetylcholinesterase inhibitors huperzine A and huperzine B

The synthesis of a new hybrid analog of the acetylcholinesterase (AChE) inhibitors huperzine A and B is reported. An intramolecular reductive dicarbonyl coupling was used as a key reaction for constructing the tetracyclic ring system.

A process for the preparation of the intermediates of the synthesis method of the huperzine-a

The invention discloses a synthesis method for preparing a huperzine A intermediate, which comprises the following steps: carrying out substitution at the alpha site of the carbonylic group by using 1,4-cyclohexyl diketone ethylene glycol and N,N-dimethylformamide dimethyl acetal as raw materials to obtain a substitution product, cyclizing the substitution product under the action of methyl cyanoacetate to obtain a cyclization product, and decarboxylating the cyclization product under the action of a strong base to obtain 2-carbonyl-6-ethylene ketal-5,7,8-dihydro-quinoline. The method has the advantages of fewer synthesis reaction steps, mild reaction conditions, low requirements for operating personnel and low environmental pollution, greatly lowers the raw material cost, and is simple to operate and convenient for refinement; and the obtained 2-carbonyl-6-ethylene ketal-5,7,8-dihydro-quinoline has high quality and high yield.

Development of a large-scale synthetic route to manufacture (-)-huperzine A

A safe, practical and scalable process for manufacture of (-)-huperzine A has been developed and scaled up to manufacture several hundred grams of (-)-huperzine A with chemical and optical purity of >99%. The process consists of 11 chemical stages starting from commercially available materials with only nine isolation steps and no chromatography purification. This process provides a reliable and cost-effective source of synthetic (-)-huperzine A and its derivatives for pharmaceutical and nutraceutical markets.