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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
Percent Composition: C 68.08%, H 6.18%, N 8.58%, O 17.16%

📌 参考资料/链接：
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).

📄 详细内容

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
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
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)
产品链接: 16625-20-0››

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