Title: Lunacrine
CAS Registry Number: 82-40-6
CAS Name: (2R)-3,9-Dihydro-8-methoxy-9-methyl-2-(1-methylethyl)furo[2,3-b]quinolin-4(2H)-one
Molecular Formula: C16H19NO3
Molecular Weight: 273.33
Percent Composition: C 70.31%, H 7.01%, N 5.12%, O 17.56%
Literature References: From bark of Lunasia costulata Miq., and L. amara Blanco, Rutaceae. Isoln: Boorsma, Bull. Inst. Bot. Buitenzorg 6, 15 (1900). Structure: Goodwin, Horning, J. Am. Chem. Soc. 81, 1908 (1959). Synthesis: Clarke, Grundon, J. Chem. Soc. 1964, 438. Stereochemistry: Bowman et al., J. Chem. Soc. Perkin Trans. 1 1973, 1051.
Properties: Fine needles from ethyl acetate, mp 117-119°. [a]25589 -50.4°; [a]25436 -116° (c = 0.806 in ethanol). Practically insol in water. Freely sol in alcohol, benzene, chloroform, ether, carbon disulfide, ethyl acetate; slightly sol in petr ether.
Melting point: mp 117-119°
Optical Rotation: [a]25589 -50.4°; [a]25436 -116° (c = 0.806 in ethanol)
Derivative Type: dl-Form
CAS Registry Number: 95723-59-4
Properties: Prisms from ethyl acetate + pentane, mp 146-148°. [a]25589 +2.3°; [a]25436 +4.2° (c = 0.864 in ethanol).
Melting point: mp 146-148°
Optical Rotation: [a]25589 +2.3°; [a]25436 +4.2° (c = 0.864 in ethanol)
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