83-58-9

Usage

Uses

Unfortunately, the provided materials do not mention any specific applications or uses for 3-[(2R)-2-hydroxy-3-methyl-butyl]-4,8-dimethoxy-1-methyl-quinolin-2-one. Further research would be required to determine its potential uses in various industries.

References

Boorsma., Meded. Lands. Plant., 31, 13, 126 (1899) Boorsma.,Bull. Inst. Bot. Buit., No. 31, 8, 25 (1904) Dieterle, Beyl., Arch. Pharm., 275, 174 (1937) Steldt, Chen.,J. Amer. Pharm. Assoc., 32, 107 (1943) Goodwin, Horning.,J. Amer. Chem. Soc., 81, 1908 (1959) Clarke, Grundon., Chem. & Ind., 556 (1962) Clarke, Grundon.,J. Chem. Soc., 438 (1964)

InChI:InChI=1/C17H23NO4/c1-10(2)13(19)9-12-16(22-5)11-7-6-8-14(21-4)15(11)18(3)17(12)20/h6-8,10,13,19H,9H2,1-5H3/t13-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 94621-58-6 4-hydroxy-3-((R)-2-hydroxy-3-methyl-butyl)-8-methoxy-1-methyl-1H-quinolin-2-one 
• 160024-36-2 3-((R)-2-Hydroxy-3-methyl-butyl)-4,8-dimethoxy-1H-quinolin-2-one 
• 77-78-1 dimethyl sulfate 
• 204707-11-9 (R)-5-(2-propyl)-dihydrofuran-2(3H)-one 
• 159973-35-0 (+)-(2'R,2''R)-3-<3'-bromo-2'-(2''-methoxy-2''-phenyl-2''-trifluoromethylacetoxy)-3'-methylbutyl>-2,4,8-trimethoxyquinoline 
• 159973-37-2 (-)-(2'R)-3-(2',3'-epoxy-3'-methylbutyl)-2,4,8-trimethoxyquinoline 
• 159973-34-9 (+/-)-3-(3'-bromo-2'-hydroxy-3'-methylbutyl)-2,4,8-trimethoxyquinoline 
• 27428-50-8 (+/-)-3-(2',3'-epoxy-3'-methylbutyl)-2,4,8-trimethoxyquinoline 
• 40042-43-1 2,4,8-trimethoxy-3-(3'-methylbut-2'-enyl)-2-quinolinone 
• 204686-75-9 (R)-N-(2-methoxy-6-methoxycarbonylphenyl)-5-methyl-4-(tetrahydropyran-2-yloxy)hexanamide 
• 204686-76-0 4-Hydroxy-8-methoxy-3-[(R)-3-methyl-2-(tetrahydro-pyran-2-yloxy)-butyl]-1H-quinolin-2-one 
• 204686-73-7 (R)-5-Methyl-4-(tetrahydro-pyran-2-yloxy)-hexanoic acid methyl ester 
• 204686-74-8 (R)-5-methyl-4-(tetrahydropyran-2-yloxy)hexanoic acid 

Relevant academic research and scientific papers

Enantioselective Synthesis and Absolute Configuration of (R)-(+)-Lunacridine and (S)-(+)-Lunacrine

(R)-(-)-Lunacridine 1 has been synthesized in 97.3percent e.e. using a chiron approach through L-valine and D-mannitol as the starting compounds to corroborate its absolute configuration.The key intermediate (S)-1,2-epoxy-3-methylbutane 11 was synthesized from (L)-valine (3 -> -> 11) and a (D)-mannitol derivative (12 -> -> 11) via functional group manipulation.The epoxide 11 was reacted with lithiated 2,4,8-trimethoxyquinoline 17 and the resulting product 18 was selectively deprotected at the 2-position followed by N-methylation of 19 to give 1.In an alternative strategy 11 was transformed into the THP-acid 23 through the chiral lactone 20.Condensation of 23 with substituted methyl anthranilate gave the amide 24 which on cyclisation, methylation and deprotection steps sequentially afforded 1.

Resolution of prenyl bromohydrin esters and derivatives: Synthesis of the quinoline alkaloid (+)-(R)- and (-)-(S)-lunacridine

Chromatographic separation of the bromohydrin MTPA diastereoisomers formed at the prenyl group attached to quinoline and coumarin rings is reported; base catalysed cyclization of the bromo MTPA esters in the quinoline series yielded the corresponding pren