[5,11,17,23-Tetratert-butyl-26,28-dihydroxy-27-(2-trimethylsilylethynyl)-25-pentacyclo[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-dodecaenyl] trifluoromethanesulfonate | 868840-63-5

• 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: [5,11,17,23-Tetratert-butyl-26,28-dihydroxy-27-(2-trimethylsilylethynyl)-25-pentacyclo[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-dodecaenyl] trifluoromethanesulfonate
• CAS: 868840-63-5
• 化学式: C₅₀H₆₃F₃O₅SSi
• 分子量: 861.194
• InChiKey: WMRMTYVTUSCULG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.42
• 重原子数：
  60
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  92.2
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [5,11,17,23-Tetratert-butyl-26,28-dihydroxy-27-(2-trimethylsilylethynyl)-25-pentacyclo[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-dodecaenyl] trifluoromethanesulfonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以85%的产率得到5,11,17,23-Tetratert-butyl-28-ethynylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaene-25,26,27-triol
  参考文献：
  名称：

  Narrow-Rim Functionalization of Calix[4]arenes via Sonogashira Coupling Reactions

  摘要：

  The narrow (or "lower")-rim hydroxyl groups of calixarenes are known to be resistant to substitution/displacement. The Sonogashira coupling reaction with TMSA and phenylacetylene, however, has now been extended to the bistriflate of p-tert-butylcalix[4]arene, previously known to be resistant to Stille, Neigishi, or Suzuki-Miyaura reactions. Under some of the reaction conditions investigated, the previously unknown narrow-rim mono- and diiodo-p-tert-butylcalix[4]arene products were also produced, in addition to the narrow-rim mono- and dialkynyl products. Homocoupling of the narrow-rim monoethynyl-p-tert-butyl-calix[4]arene produced a new narrow-rim rigid butadiyne-linked bis-p-tert-butylcalix[4]arene.

  DOI：

  10.1021/jo050488s
• 作为产物：
  描述：

  1,3-bis(triflate)-p-tert-butylcalix[4]arene 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以51%的产率得到[5,11,17,23-Tetratert-butyl-26,28-dihydroxy-27-(2-trimethylsilylethynyl)-25-pentacyclo[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-dodecaenyl] trifluoromethanesulfonate
  参考文献：
  名称：

  Narrow-Rim Functionalization of Calix[4]arenes via Sonogashira Coupling Reactions

  摘要：

  The narrow (or "lower")-rim hydroxyl groups of calixarenes are known to be resistant to substitution/displacement. The Sonogashira coupling reaction with TMSA and phenylacetylene, however, has now been extended to the bistriflate of p-tert-butylcalix[4]arene, previously known to be resistant to Stille, Neigishi, or Suzuki-Miyaura reactions. Under some of the reaction conditions investigated, the previously unknown narrow-rim mono- and diiodo-p-tert-butylcalix[4]arene products were also produced, in addition to the narrow-rim mono- and dialkynyl products. Homocoupling of the narrow-rim monoethynyl-p-tert-butyl-calix[4]arene produced a new narrow-rim rigid butadiyne-linked bis-p-tert-butylcalix[4]arene.

  DOI：

  10.1021/jo050488s

文献信息

• Narrow-Rim Functionalization of Calix[4]arenes via Sonogashira Coupling Reactions
  作者：Hassan Al-Saraierh、David O. Miller、Paris E. Georghiou

  DOI：10.1021/jo050488s

  日期：2005.10.1

  The narrow (or "lower")-rim hydroxyl groups of calixarenes are known to be resistant to substitution/displacement. The Sonogashira coupling reaction with TMSA and phenylacetylene, however, has now been extended to the bistriflate of p-tert-butylcalix[4]arene, previously known to be resistant to Stille, Neigishi, or Suzuki-Miyaura reactions. Under some of the reaction conditions investigated, the previously unknown narrow-rim mono- and diiodo-p-tert-butylcalix[4]arene products were also produced, in addition to the narrow-rim mono- and dialkynyl products. Homocoupling of the narrow-rim monoethynyl-p-tert-butyl-calix[4]arene produced a new narrow-rim rigid butadiyne-linked bis-p-tert-butylcalix[4]arene.