calix[1]-3-chloropyridine[3]pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: calix[1]-3-chloropyridine[3]pyrrole
• 英文别名: 19-Chloro-2,2,7,7,12,12,17,17-octamethyl-22,23,24,25-tetrazapentacyclo[16.3.1.13,6.18,11.113,16]pentacosa-1(22),3,5,8,10,13,15,18,20-nonaene
• 化学式: C₂₉H₃₅ClN₄
• 分子量: 475.077
• InChiKey: RFGMCUJZCGRWJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  60.3
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  sodium trichloroacetate 、 MESO-八甲基杯(4)吡咯 以 N,N-二甲基甲酰胺 为溶剂， 以45%的产率得到calix[1]-3-chloropyridine[3]pyrrole
  参考文献：
  名称：

  Missing-Link Macrocycles: Hybrid Heterocalixarene Analogues Formed from Several Different Building Blocks

  摘要：

  The synthesis and structural characterization of hybrid heterocalix[4]arene analogues containing pyrrole, benzene, methoxy-substituted benzene, and pyridine subunits is described. Macrocycles I and 2, examples of calix[2]benzene[2]pyrrole and calix[I]benzene[3]pyrrole systems, respectively, are synthesized by the condensation of pyrrole and an appropriate pheny Ibis (carbinol). Macrocycles 3 and 7, examples of calix[2] benzene[ 1]pyridine [ 1]pyrrole and calix[1]pyridine[3]pyrrole, respectively, are synthesized by the use of a carbene-based pyrrole-to-pyridine ring-expansion procedure. Single-crystal X-ray analysis reveals that compounds la, 1b, and 2b adopt 1,3-alternate conformations in the solid state, whereas compounds 3 and 7 display structures that are best described as "flattened partial cones" in terms of their conformation. (Series a refers to pure benzene-derived systems, whereas series b indicates macrocycles containing 5-mothoxyphenyl subunits). In the solid state, the methoxy-functionalized macrocycles I b and 2b, and the chloropyridine-containing macrocycle 7 exist as dimers. In the case of la and 7, these compounds interact with neutral solvent in the solid state. The conformations of the macrocycles in solution were explored by temperature-dependent proton NMR and NOESY spectral analysis. At 188K, macrocycles I a and 2 a adopt flattened 1,3-alternate conformations, whereas macrocycles 3 and 7 exist in the form of flattened partial-cone conformations. Standard proton NMR titration analyses were carried out in the case of macrocycles I a and 2 a, and reveal that at least the second of these systems is capable of binding fluoride and chloride anions in CD,Cl, solution at room temperature (K-a = 571 and 17 M-1 in the case of 2 a and F- and Cl, respectively).

  DOI：

  10.1002/1521-3765(20020301)8:5<1134::aid-chem1134>3.0.co;2-m

文献信息

• Calix[4]pyridine: a new arrival in the heterocalixarene family
  作者：Vladimír Král、Philip A. Gale、Pavel Anzenbacher Jr.、Karolina Jursíková、Vincent Lynch、Jonathan L. Sessler、Vladimír Král、Pavel Anzenbacher Jr.

  DOI：10.1039/a706018a

  日期：——

  Reaction of dichlorocarbene with meso-octamethylcalix[4]pyrrole causes pyrrole ring expansion, producing chlorocalixpyridinopyrroles and chlorocalixpyridines.

  二氯羰基与中-八甲基钙[4]吡咯的反应会导致吡咯环扩张，生成氯代吡啶和氯代吡啶。
• Missing-Link Macrocycles: Hybrid Heterocalixarene Analogues Formed from Several Different Building Blocks
  作者：Jonathan L. Sessler、Won-Seob Cho、Vincent Lynch、Vladimír Král

  DOI：10.1002/1521-3765(20020301)8:5<1134::aid-chem1134>3.0.co;2-m

  日期：2002.3.1

  The synthesis and structural characterization of hybrid heterocalix[4]arene analogues containing pyrrole, benzene, methoxy-substituted benzene, and pyridine subunits is described. Macrocycles I and 2, examples of calix[2]benzene[2]pyrrole and calix[I]benzene[3]pyrrole systems, respectively, are synthesized by the condensation of pyrrole and an appropriate pheny Ibis (carbinol). Macrocycles 3 and 7, examples of calix[2] benzene[ 1]pyridine [ 1]pyrrole and calix[1]pyridine[3]pyrrole, respectively, are synthesized by the use of a carbene-based pyrrole-to-pyridine ring-expansion procedure. Single-crystal X-ray analysis reveals that compounds la, 1b, and 2b adopt 1,3-alternate conformations in the solid state, whereas compounds 3 and 7 display structures that are best described as "flattened partial cones" in terms of their conformation. (Series a refers to pure benzene-derived systems, whereas series b indicates macrocycles containing 5-mothoxyphenyl subunits). In the solid state, the methoxy-functionalized macrocycles I b and 2b, and the chloropyridine-containing macrocycle 7 exist as dimers. In the case of la and 7, these compounds interact with neutral solvent in the solid state. The conformations of the macrocycles in solution were explored by temperature-dependent proton NMR and NOESY spectral analysis. At 188K, macrocycles I a and 2 a adopt flattened 1,3-alternate conformations, whereas macrocycles 3 and 7 exist in the form of flattened partial-cone conformations. Standard proton NMR titration analyses were carried out in the case of macrocycles I a and 2 a, and reveal that at least the second of these systems is capable of binding fluoride and chloride anions in CD,Cl, solution at room temperature (K-a = 571 and 17 M-1 in the case of 2 a and F- and Cl, respectively).