The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 3-Hydroxy-3-phenylpropanenitrile( cas:17190-29-3 ) is researched.Category: pyrazoles-derivatives.Kalvoda, Jaroslav; Kaufmann, Heinz published the article 《Cleavage of carbon-carbon double bonds by a novel cycloaddition-cycloreversion sequence》 about this compound( cas:17190-29-3 ) in Journal of the Chemical Society, Chemical Communications. Keywords: cycloaddition dipolar ethoxycarbonylformonitrile alkene; decarboxylation isoxazolinecarboxylate; androstane methylene cycloaddition ethoxycarbonylformonitrile; styrene cycloaddition ethoxycarbonylformonitrile; stilbene cycloaddition ethoxycarbonylformonitrile. Let’s learn more about this compound (cas:17190-29-3).
Carbon-carbon double bonds are cleaved with simultaneous generation of a carbonyl compound and a nitrile by a sequence involving 1,3-dipolar cycloaddition of EtO2CCNO to the alkene, followed by hydrolysis of the 3-ethoxycarbonylisoxazoline, which is formed, to give the free acid, and subsequent thermal decarboxylation. Thus treatment of the 3-methylene steroid I (RR1 = CH2, R2 = Ac) with EtO2CCNO gave 39% spiroisoxazoline II (R = Et, R2 = Ac) which on saponification with KOH-MeOH-H2O at 20° gave the free acid II (R = R2 = H). Subsequent thermal decarboxylation of II (R = R2 = H) at 130° in DMF for 1 hr gave 90-2% hydroxynitrile I (R = OH, R1 = CH2CN, R2 = H). Styrene and stilbene underwent similar reactions.
There is still a lot of research devoted to this compound(SMILES：N#CCC(O)C1=CC=CC=C1)Category: pyrazoles-derivatives, and with the development of science, more effects of this compound(17190-29-3) can be discovered.
Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics