5-Chloro-28-iodo-2,8,14,20-tetramethyl-2,8,14,20,25,26,27-heptazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene | 1370008-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Chloro-28-iodo-2,8,14,20-tetramethyl-2,8,14,20,25,26,27-heptazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene
• CAS: 1370008-90-4
• 化学式: C₂₅H₂₃ClIN₇
• 分子量: 583.862
• InChiKey: CZQLLQDEKHHYIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (5-Chloro-2,8,14,20-tetramethyl-2,8,14,20,25,26,27-heptazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaen-28-yl) trifluoromethanesulfonate 在 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 、 potassium iodide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到5-Chloro-28-iodo-2,8,14,20-tetramethyl-2,8,14,20,25,26,27-heptazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene
  参考文献：
  名称：

  Copper(I)-Catalyzed Halogenation and Acyloxylation of Aryl Triflates through a Copper(I)/Copper(III) Catalytic Cycle

  摘要：

  Catalyzed by CuOTf under very mild conditions, aryl triflates which are embedded in the azacalix[1]-arene[3]pyridine macrocycle underwent coupling reactions with metal halides and acetates to afford respectively halogenated and acyloxylated arene products in moderate to excellent yields. The unprecedented CuOTf-catalyzed transformations of aryl triflates proceeded through an oxidative addition of intramolecularly chelated Cu(I) into the C-O bond of aryl triflates to form arylcopper(III) intermediates which underwent anion exchange and reductive elimination reactions with nucleophiles to yield functionalized macrocyclic products.

  DOI：

  10.1021/om500046g

文献信息

• Cu(ClO₄)₂-Mediated Arene C–H Bond Halogenations of Azacalixaromatics Using Alkali Metal Halides as Halogen Sources
  作者：Bo Yao、Zu-Li Wang、Hu Zhang、De-Xian Wang、Liang Zhao、Mei-Xiang Wang

  DOI：10.1021/jo300152u

  日期：2012.4.6

  Regiospecific halogenation of azacalix[1]arene[3]pyridines at the lower rim position of the benzene ring was achieved from their cross-coupling reaction with cost-effective alkali metal halides through the Cu(ClO4)2-mediated aerobic aryl C–H activation, which gave structurally well-defined aryl-Cu(III) intermediates, and a subsequent C–X bond formation reaction under very mild conditions.

  氮杂杯[1]芳烃[3]吡啶在苯环较低边缘位置的区域特异性卤化反应是通过它们与具成本效益的碱金属卤化物通过Cu（ClO 4）2介导的好氧芳基C–的交叉偶联反应实现的。H活化，产生结构上明确的芳基-Cu（III）中间体，随后在非常温和的条件下形成C-X键。