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首页> 外文期刊>Chemistry: A European journal >The Synthesis and Characterization of all Diastereomers of a Linear Symmetrically Fused Tris-Troger's Base Analogue:New Chiral Cleft Compounds
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The Synthesis and Characterization of all Diastereomers of a Linear Symmetrically Fused Tris-Troger's Base Analogue:New Chiral Cleft Compounds

机译：线性对称融合的Tris-Troger碱基类似物的所有非对映异构体的合成和表征：新的手性裂隙化合物

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摘要

The synthesis and characterization of all diastereomers of a linear symmetrically fused tris-Troger's base analogue are described.The diastereomers are unambiguously assigned as syn-anti 1a,anti-anti 1b,and syn-syn 1c isomers,by using X-ray diffraction analysis and NMR spectroscopy.For the first time,the anti-anti and the syn-syn diastereomers of a linear symmetrically fused tris-Troger's base analogue have been synthesized.Molecules 1a and 1c are new cleft compounds and analysis of compound 1a in the solid state shows inclusion of one molecule of CH_2Cl_2 in the larger aromatic cleft,whereas in isomer 1c disordered solvent molecules are trapped in the extended aromatic cleft.Furthermore,in the solid state,isomer 1c forms infinite open channels along one of the crystallographic axes and perpendicular to this axis there are infinitely extending "wedged-ravines".Importantly,each of the diastereomers 1a-c is resistant to inversion at the stereogenic nitrogen atoms under strongly and weakly acidic conditions in the range from room temperature(RT)to 95 deg C.This observed configurational stability at the stereogenic nitrogens of 1a-c is unique for analogues of Tro-ger's base in general to date.Finally,the ratio of cleft compounds 1a and 1c significantly increased relative to cavity compound 1b when ammonium chloride was used as an additive in the Tro-ger's base condensation to 1a-c suggesting a templating effect of the ammonium ion.
机译：描述了线性对称稠合的tris-Troger碱基类似物的所有非对映异构体的合成和表征。通过X射线衍射分析，将非对映异构体明确指定为syn-anti 1a，anti-anti 1b和syn-syn 1c异构体。首次合成了线性对称稠合的tris-Troger碱基类似物的反-和反-syn-syn非对映异构体。分子1a和1c是新的裂隙化合物，并且对化合物1a进行了固态分析表示在较大的芳族裂隙中包含一个CH_2Cl_2分子，而在异构体1c中无序的溶剂分子被捕获在扩展的芳族裂隙中。此外，在固态下，异构体1c沿​​结晶轴之一并垂直于重要的是，每个非对映异构体1a-c在强和弱的条件下都抵抗立体异构氮原子的反转在室温（RT）至95摄氏度的酸性条件下。在1a-c立体立体氮上观察到的构型稳定性迄今为止对于Tro-ger碱的类似物而言是迄今为止唯一的。最后，裂缝化合物的比例当氯化铵被用作Troger碱缩合成1a-c的添加剂时，图1a和1c相对于空腔化合物1b显着增加，表明了铵离子的模板作用。

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