(19Z)-Anhydrovobasinediol Chemical Properties

Melting point:

20So C (dec.).

Boiling point:

490.6±45.0 °C(Predicted)

Density 

1.213±0.06 g/cm3(Predicted)

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

17.39±0.20(Predicted)

(19Z)-Anhydrovobasinediol Usage And Synthesis

Description

An alkaloid which occurs in Tabernaemontana psychotrifolia H.B.K., this base is laevorotatory having [α]>_D - 243° and gives an ultraviolet spectrum with absorption maxima at 222, 2S0 and 296 mp. with a shoulder at 272 mil. The alkaloid may be purified by recrystallization from Me2CO followed by sublima_x0002_tion. It yields a crystalline methiodide, m.p. 272-4°C (dec.) which has an ultraviolet spectrum containing an absorption maximum at 222 mp. and a shoulder at 276 mp.. On catalytic hydrogenation with Pt02 as catalyst it gives the dihydro derivative, m.p. 191-3°C, furnishing a methiodide, m.p. 265-SoC (dec.). Zn dust distillation yields 3-ethylpyridine and 3-methyl-5-ethylpyridine.

References

Benoin, Burnell, Medina., Tetrahedron Lett., 807 (1968)
Burnell, Medina., Can. J. Chem., 49,307 (1971)