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 | 868840-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 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
• CAS: 868840-72-6
• 化学式: C₄₆H₅₆O₃
• 分子量: 656.949
• InChiKey: QMAHLWLYLPEJKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  49
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  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 在 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 0.25h， 以68%的产率得到5,11,17,23-Tetratert-butyl-28-[4-(5,11,17,23-tetratert-butyl-26,27,28-trihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaenyl)buta-1,3-diynyl]pentacyclo[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：

  [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