54318-59-1

Basic information

• Product Name: mappicine
• Synonyms: mappicine;(S)-Mappicine;7-[(S)-1-Hydroxypropyl]-8-methyl-9,11-dihydroindolizino[1,2-b]quinoline-9-one;7-[(S)-1-Hydroxypropyl]-8-methylindolizino[1,2-b]quinolin-9(11H)-one;Mappicin
• CAS NO: 54318-59-1
• Molecular Formula: C19H18N2O2
• Molecular Weight: 306.35842
• Mol File: 54318-59-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 616°C at 760 mmHg
• Flash Point: 326.3°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 4.97E-16mmHg at 25°C
• Refractive Index: 1.7
• CAS DataBase Reference: mappicine(CAS DataBase Reference)
• NIST Chemistry Reference: mappicine(54318-59-1)
• EPA Substance Registry System: mappicine(54318-59-1)

Safety Data

• Hazardous Substances Data: 54318-59-1(Hazardous Substances Data)

Usage

Description

Mappia foetida contains this alkaloid which is a minor constituent of the alkaloidal extract. The base has been partially synthesized from camptothecin.

References

Govindacharietal.,l. Chem. Soc., Perkin !, 1215 (1974)

InChI:InChI=1/C19H18N2O2/c1-3-17(22)14-9-16-18-13(10-21(16)19(23)11(14)2)8-12-6-4-5-7-15(12)20-18/h4-9,17,22H,3,10H2,1-2H3

Upstream product

• 1197040-29-1 phenyl isocyanate 
• 192189-66-5 6-Bromo-4-((S)-1-hydroxy-propyl)-3-methyl-1-prop-2-ynyl-1H-pyridin-2-one 
• 55854-89-2 8-methyl-7-propionylindolizino[1,2-b]quinoline-9(11H)-one 
• 55822-01-0 7-(1-acetoxy-propyl)-8-methyl-11H-indolizino[1,2-b]quinolin-9-one 
• 54318-60-4 (S)-mappicine acetate 
• 340128-80-5 7-{1-[(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)-diisopropyl-silanyloxy]-propyl}-8-methyl-11H-indolizino[1,2-b]quinolin-9-one 
• 227455-96-1 trans-Δ^19,20-20-O-acetylmappicine 
• 227455-97-2 cis-Δ^19,20-20-O-acetylmappicine 
• 305816-10-8 (S)-1-(2-Methoxy-3-methyl-6-trimethylsilanyl-pyridin-4-yl)-propan-1-ol 
• 340128-74-7 (4S)-[diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorooctyl)silanyloxypropyl]-2-methoxyl-3-methyl-6-trimethylsilanylpyridine 
• 54352-77-1 (+/-)-mappicine 
• 192189-64-3 6-Bromo-1-(tert-butyl-diphenyl-silanyl)-4-((S)-1-hydroxy-propyl)-3-methyl-1H-pyridin-2-one 
• 192189-65-4 6-Bromo-4-((S)-1-hydroxy-propyl)-3-methyl-1H-pyridin-2-one 
• 201597-93-5 (E)-4-(3-Methoxymethyl-quinolin-2-yl)-4-oxo-but-2-enoic acid ethyl ester 

Downstream Products

• 55854-89-2 8-methyl-7-propionylindolizino[1,2-b]quinoline-9(11H)-one 

Relevant articles and documents

The first conversion of camptothecin to (S)-mappicine by an efficient chemoenzymatic method

Camptothecin has been converted for the first time to (S)-mappicine via mappicine ketone, which is the sole product of the microwave irradiation of camptothecin. Baker's yeast reduction of mappicine ketone yielded (S)- mappicine in high optical purity.

Chemoenzymatic synthesis of (S)- and (R)-mappicines and their analogues

The natural alkaloids, camptothecin and mappicine ketone were converted into racemic mappicine which on treatment with vinyl acetate in presence of the lipase Candida cylindracea (CCL) afforded (S)-mappicine acetate and (R)-mappicine. The acetate was chemically hydrolysed to (S)-mappicine. 9-Methoxycamtpothecin and 9-methoxymappicine ketone were similarly converted into (S)- and (R)-9-methoxymappicines.

Total synthesis of nothapodytine b and (-)-mappicine

Concise total syntheses of naturally occurring nothapodytine B (1, mappicine ketone) and ( - )-mappicine (3) are detailed. The approach is based on the implememation of a room-temperature, inverse electron demand Diels-Alder reaction of the N-sulfonyl-1-aza-1.3-butadiene 11 for assemblage of a pyridone 1) ring precursor central to the structure. A Friedlander condensation is utilized for constructing the AB ring system of 1 and 3. An acid-catalyzed reaction sequence is used to accomplish a deprotection with subsequent ring-closure for introduction of the C ring in a single step.