Molecular design of organic superbases, azacalix[3](2,6)pyridines: catalysts for 1,2- and 1,4-additions.
Molecular design of organic superbases, azacalix[3](2,6)pyridines: catalysts for 1,2- and 1,4-additions.
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DOI：
10.1021/jo3017428
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发表时间：
2012-11
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影响因子：
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通讯作者：
Natsuko Uchida;J. Kuwabara;Ayako Taketoshi;T. Kanbara
中科院分区：
文献类型：
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作者：
Natsuko Uchida;J. Kuwabara;Ayako Taketoshi;T. Kanbara
研究了大环氨基化合物氮杂杯[3]（2，6）吡啶衍生物的分子设计、性质和催化活性。通过在吡啶上引入给电子基团和氨基苯基桥连，氮杂杯[3]（2，6）吡啶在CD（3）CN中的碱性提高到pK（BH（+））= 29.5。这些衍生物被证明是有效的催化剂，用于硝基烷烃或伯醇与α，β-不饱和羰基化合物的1，4-加成反应和硝基烷烃与芳香醛的1，2-加成反应。
The molecular design, characteristics, and catalytic activity of macrocyclic amino compounds, azacalix[3](2,6)pyridine derivatives, were studied. The introduction of an electron-donating group on the pyridine moiety and bridging amino phenyl group enabled the enhancement of the basicity of azacalix[3](2,6)pyridine up to pK(BH(+)) = 29.5 in CD(3)CN. These derivatives were shown to be efficient catalysts for 1,4-addition reactions of nitroalkanes or primary alcohols to α,β-unsaturated carbonyl compounds and 1,2-addition reactions of nitroalkanes to aromatic aldehydes.