Haplophytine
Structural Formula Vector Image
Title: Haplophytine
CAS Registry Number: 16625-20-0
CAS Name: [15(3aS,7R)]-3,4-Didehydro-19-hydroxy-16,17-dimethoxy-1-methyl-15-(2,3,5,6-tetrahydro-11-hydroxy-4-methyl-1,13-dioxo-1H-3a,7-methanopyrrolo[1,2-a][1,3]benzodiazocin-7(4H)-yl)aspidospermidin-21-oic acid g-lactone
Molecular Formula: C37H40N4O7
Molecular Weight: 652.74
Percent Composition: C 68.08%, H 6.18%, N 8.58%, O 17.16%
Literature References: Insecticidal alkaloid from the Mexican plant Haplophyton cimicidum A. DC., Apocynaceae: Rogers et al., J. Am. Chem. Soc. 74, 1987 (1952); 76, 2819 (1954). Partial structure: Snyder et al., ibid. 80, 3708 (1958). Structure: Rae et al., ibid. 89, 3061 (1967). Crystal structure and absolute config.: Zacharias, Acta Crystallogr. 26B, 1455 (1970). Synthetic approaches: P. Yates, D. A. Schwartz, Can. J. Chem. 61, 509 (1983). Review: Yates et al., J. Am. Chem. Soc. 95, 7842 (1973).
Properties: Crystals from ethanol + chloroform, mp 290-293° (rapid heating, starting at 250°). Also reported as mp 300-302° (Yates et al., loc. cit.). [a]D25 +109.0° (chloroform). uv max (ethanol): 220, 265, 305 nm (e 48500, 14300, 4500). Very sol in chloroform, benzene, dioxane, ethyl acetate. Moderately sol in acetone, methanol, somewhat less in ethanol. Practically insol in water, ether, petr ether. Readily sol in dil acids or alkalies.
Melting point: mp 290-293° (rapid heating, starting at 250°); mp 300-302° (Yates et al., loc. cit.)
Optical Rotation: [a]D25 +109.0° (chloroform)
Absorption maximum: uv max (ethanol): 220, 265, 305 nm (e 48500, 14300, 4500)
 
Derivative Type: Dihydrochloride
Molecular Formula: C27H31N3O5.2HCl
Molecular Weight: 550.47
Percent Composition: C 58.91%, H 6.04%, N 7.63%, O 14.53%, Cl 12.88%
Properties: Dec 208-218° (darkens at 200°).
 
Derivative Type: O-Methylhaplophytine
Molecular Formula: C28H33N3O5
Molecular Weight: 491.58
Percent Composition: C 68.41%, H 6.77%, N 8.55%, O 16.27%
Properties: Crystals from ether + ethanol, dec 288-291°. [a]D24 +12° (c = 4.37 in chloroform).
Optical Rotation: [a]D24 +12° (c = 4.37 in chloroform)

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