Title: Echinuline
CAS Registry Number: 1859-87-6
CAS Name: (3S-cis)-3-[[2-(1,1-Dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1H-indol-3-yl]methyl]-6-methyl-2,5-piperazinedione
Molecular Formula: C29H39N3O2
Molecular Weight: 461.64
Percent Composition: C 75.45%, H 8.52%, N 9.10%, O 6.93%
Literature References: From the dry mycelia of Aspergillus echinulatus: Quilico, Panizzi, Ber. 76, 348 (1943). Structure: Casnati et al., Gazz. Chim. Ital. 92, 105 (1962); Romanet et al., Bull. Soc. Chim. Fr. 1963, 1048. Absolute configuration: Nakashima, Slater, Tetrahedron Lett. 1967, 4433; 1971, 2649. Synthetic studies: Houghton, Saxton, J. Chem. Soc. C 1969, 595, 1003; Takamatsu et al., Tetrahedron Lett. 1971, 4661. Total synthesis of optically active cis isomer: eidem, ibid. 4665; S. Inoue et al., J. Pharm. Soc. Jpn. 97, 558 (1977). Epimerization of echinuline with triethylamine in ethanol gives the trans isomer, epi-echinuline, Westley et al., Anal. Chem. 40, 1888 (1968).
Properties: Needles from butanol, mp 242-243°. [a]D20 -26.0° (chloroform). uv max (ethanol): 230, 279, 286 nm (log e 4.60, 3.98, 3.96). Sol in glacial acetic acid, chloroform, pyridine, dioxane; less sol in warm alcohol, warm butanol; slightly sol in benzene, ether, petr ether, carbon tetrachloride, acetone, cold alcohol.
Melting point: mp 242-243°
Optical Rotation: [a]D20 -26.0° (chloroform)
Absorption maximum: uv max (ethanol): 230, 279, 286 nm (log e 4.60, 3.98, 3.96) |