(5-Cyano-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 | 1555841-41-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (5-Cyano-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
• 英文别名: (5-cyano-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
• CAS: 1555841-41-2
• 化学式: C₂₇H₂₃F₃N₈O₃S
• 分子量: 596.593
• InChiKey: GRJXCKOCPPWEAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  42
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (5-Cyano-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78%的产率得到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-5-carbonitrile
  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
• 作为产物：
  描述：

  三氟甲磺酸酐 、 28-Hydroxy-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-5-carbonitrile 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以81%的产率得到(5-Cyano-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
  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

• Copper(I)-Catalyzed Halogenation and Acyloxylation of Aryl Triflates through a Copper(I)/Copper(III) Catalytic Cycle
  作者：Chao Long、Liang Zhao、Jing-Song You、Mei-Xiang Wang

  DOI：10.1021/om500046g

  日期：2014.2.24

  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.