5-(p-C7H15Ph)-7-azaindole | 1205548-87-3

• 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: 5-(p-C7H15Ph)-7-azaindole
• CAS: 1205548-87-3
• 化学式: C₂₀H₂₄N₂
• 分子量: 292.424
• InChiKey: FCQDUTRRBJPFTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  28.68
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,2,4,5-四溴苯 、 5-(p-C7H15Ph)-7-azaindole 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以42%的产率得到TPAB
  参考文献：
  名称：

  New Bimetallic Reactivity in Pt₂^II,II/Pt₂^IV,IV Transformation Mediated by a Benzene Ring

  摘要：

  A new Pt-2(II,II) complex with the formula Pt-2(TPAB)Me-4 (1), where TPAB = 1,2,4,5-tetrakis(5-(p-C tau-H15Ph)-7-azaindol-1-yl)benzene, has been synthesized. This molecule has excellent solubility in common solvents, which enabled our investigation of its reactions with a variety of oxidants to form Pt-2(IV,IV) species and the reverse reactions of the Pt-2(IV,IV) species back to 1 via reduction. Despite the lack of direct Pt...Pt interactions, the two Pt centers in 1 display distinct bimetallic cooperativity mediated by the central phenyl ring of the TPAB ligand. The most unusual Finding is that the reactivity of I with MeOTf is highly dependent on the amount of molecular oxygen present in the reaction medium. In the absence of O-2, the reaction of 1 with MeOTf produced [Pt-2(IV,IV)(TPAB)Me-6][OTf](2) (6), while in the presence of O-2, complex 7, Pt-2(IV,IV)(TPAB)Me-4(OTf)(2), was obtained. Compound 1 was found to react readily with O-2 at one atmosphere and ambient temperature to produce an insoluble and not yet fully characterized solid that further reacts with MeOTf to produce 7 quantitatively. NMR and single-crystal X-ray diffraction analyses established that the two Pt-IV centers in 6 are five-coordinate with a square-pyramidal geometry, while in 7 the two Pt-IV centers are six-coordinate with an octahedral geometry. Most significantly, the central phenyl ring of the TPAB ligand was transformed to a cyclohexyldienyl in 7, while it remains unchanged in 6. Complex 1 also reacts readily with other oxidants such as CHCl3, PhICl2, Br-2 (CBr4), I-2, and H2O2 to produce Pt-2(IV,IV)(TPAB)Me4X2 (X = Cl, 2; Br, 3; 1, 4; OH, 5). The structures of 2-5 are similar to that of 7, showing the generality of the central phenyl ring mediated oxidation of the Pt-2(II,II) system. Complexes 2 and 7 call be reduced and converted back to complex 1 via reactions with BH4-, its established by NMR experiments.

  DOI：

  10.1021/om901046p
• 作为产物：
  描述：

  4-N-庚基苯硼酸 、 5-溴-7-氮杂吲哚 在 [Pd] 作用下， 以81%的产率得到5-(p-C7H15Ph)-7-azaindole
  参考文献：
  名称：

  New Bimetallic Reactivity in Pt₂^II,II/Pt₂^IV,IV Transformation Mediated by a Benzene Ring

  摘要：

  A new Pt-2(II,II) complex with the formula Pt-2(TPAB)Me-4 (1), where TPAB = 1,2,4,5-tetrakis(5-(p-C tau-H15Ph)-7-azaindol-1-yl)benzene, has been synthesized. This molecule has excellent solubility in common solvents, which enabled our investigation of its reactions with a variety of oxidants to form Pt-2(IV,IV) species and the reverse reactions of the Pt-2(IV,IV) species back to 1 via reduction. Despite the lack of direct Pt...Pt interactions, the two Pt centers in 1 display distinct bimetallic cooperativity mediated by the central phenyl ring of the TPAB ligand. The most unusual Finding is that the reactivity of I with MeOTf is highly dependent on the amount of molecular oxygen present in the reaction medium. In the absence of O-2, the reaction of 1 with MeOTf produced [Pt-2(IV,IV)(TPAB)Me-6][OTf](2) (6), while in the presence of O-2, complex 7, Pt-2(IV,IV)(TPAB)Me-4(OTf)(2), was obtained. Compound 1 was found to react readily with O-2 at one atmosphere and ambient temperature to produce an insoluble and not yet fully characterized solid that further reacts with MeOTf to produce 7 quantitatively. NMR and single-crystal X-ray diffraction analyses established that the two Pt-IV centers in 6 are five-coordinate with a square-pyramidal geometry, while in 7 the two Pt-IV centers are six-coordinate with an octahedral geometry. Most significantly, the central phenyl ring of the TPAB ligand was transformed to a cyclohexyldienyl in 7, while it remains unchanged in 6. Complex 1 also reacts readily with other oxidants such as CHCl3, PhICl2, Br-2 (CBr4), I-2, and H2O2 to produce Pt-2(IV,IV)(TPAB)Me4X2 (X = Cl, 2; Br, 3; 1, 4; OH, 5). The structures of 2-5 are similar to that of 7, showing the generality of the central phenyl ring mediated oxidation of the Pt-2(II,II) system. Complexes 2 and 7 call be reduced and converted back to complex 1 via reactions with BH4-, its established by NMR experiments.

  DOI：

  10.1021/om901046p