83-58-9

Basic information

• Product Name: 3-[(2R)-2-hydroxy-3-methyl-butyl]-4,8-dimethoxy-1-methyl-quinolin-2-on e
• Synonyms: 3-[(2R)-2-hydroxy-3-methyl-butyl]-4,8-dimethoxy-1-methyl-quinolin-2-on e;C10710;Lunacridine
• CAS NO: 83-58-9
• Molecular Formula: C17H23NO4
• Molecular Weight: 0
• Mol File: 83-58-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 86-87°
• Boiling Point: 449.4°C at 760 mmHg
• Flash Point: 225.6°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 7.28E-09mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: 3-[(2R)-2-hydroxy-3-methyl-butyl]-4,8-dimethoxy-1-methyl-quinolin-2-on e(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(2R)-2-hydroxy-3-methyl-butyl]-4,8-dimethoxy-1-methyl-quinolin-2-on e(83-58-9)
• EPA Substance Registry System: 3-[(2R)-2-hydroxy-3-methyl-butyl]-4,8-dimethoxy-1-methyl-quinolin-2-on e(83-58-9)

Safety Data

• Hazardous Substances Data: 83-58-9(Hazardous Substances Data)

Usage

Description

This alkaloid was first described by Boorsma who obtained it from the bark of Lunasia costulata Miq (Syn. L. amara Blanco). The base is a quinolone derivative and crystallizes as colourless needles from AcOEt. It is dextrorotatory having [α]24D + 30.1 ° and [α]24436 + 81.8°. Boorsma gives a specific rotation of [α]28D + 31.6°. The solutions of the alkaloid show a weak blue fluorescence in artificial light. A crystalline perchlorate is known, m.p. 146-8°C and 193-5°C after intermediate solidification. This salt is also dextrorotatory with [α]2558925436+ 60.7°. The structure has been demonstrated to be 3-(2-hydroxy-3- methylbutyl)-4: 8-dimethoxy-l-methyl-2-quinolone. The alkaloid described under this name by Dieterle and Beyl appears to be identical with lunamarine (q.v.).

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 
• 74-88-4 methyl iodide 
• 204686-77-1 4,8-Dimethoxy-1-methyl-3-[(R)-3-methyl-2-(tetrahydro-pyran-2-yloxy)-butyl]-1H-quinolin-2-one 
• 77-78-1 dimethyl sulfate 
• 159973-38-3 (+)-(2'R)-3-(2'-hydroxy-3'-methylbutyl)-2,4,8-trimethoxyquinoline 
• 204707-11-9 (R)-5-(2-propyl)-dihydrofuran-2(3H)-one 
• 204686-72-6 (R)-4-Hydroxy-5-methyl-hexanoic acid methyl ester 
• 204686-74-8 (R)-5-methyl-4-(tetrahydropyran-2-yloxy)hexanoic acid 
• 204686-73-7 (R)-5-Methyl-4-(tetrahydro-pyran-2-yloxy)-hexanoic acid methyl ester 
• 204686-76-0 4-Hydroxy-8-methoxy-3-[(R)-3-methyl-2-(tetrahydro-pyran-2-yloxy)-butyl]-1H-quinolin-2-one 
• 204686-75-9 (R)-N-(2-methoxy-6-methoxycarbonylphenyl)-5-methyl-4-(tetrahydropyran-2-yloxy)hexanamide 
• 40042-43-1 2,4,8-trimethoxy-3-(3'-methylbut-2'-enyl)-2-quinolinone 

Relevant articles and documents

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.