5,11,17,23-tetra-tert-butyl-25,27-bis(cyanomethoxy)-26,28-dihydroxythiacalix[4]arene | 678195-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23-tetra-tert-butyl-25,27-bis(cyanomethoxy)-26,28-dihydroxythiacalix[4]arene
• 英文别名: 1,3-bis(O-cyanomethyl)-p-tert-butylthiacalix[4]arene；2-[[5,11,17,23-Tetratert-butyl-27-(cyanomethoxy)-26,28-dihydroxy-2,8,14,20-tetrathiapentacyclo[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-25-yl]oxy]acetonitrile
• CAS: 678195-15-8
• 化学式: C₄₄H₅₀N₂O₄S₄
• 分子量: 799.156
• InChiKey: ZZTYMLRZUUKVJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.8
• 重原子数：
  54
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  208
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-tert-butyl-25,27-bis(cyanomethoxy)-26,28-dihydroxythiacalix[4]arene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以20%的产率得到25,27-bis(2-aminoethoxy)-5,11,17,23-tetra-tert-butyl-26,28-dihydroxythiacalix[4]arene
  参考文献：
  名称：

  Stereoselective synthesis of all stereoisomers of vicinal and distal bis(O-2-aminoethyl)-p-tert-butylthiacalix[4]arene

  摘要：

  O,O"- and O,O'-bis(2-aminoethyl)-p-tert-butylthiacalix[4]arenes of anti conformation have been prepared by the reduction of the corresponding O,O"- and O,O'-bis(cyanomethyl) ethers. Their syn-O,O"- and O,O'-counterparts have been prepared by alternative routes via the Mitsunobu reaction of thiacalix[4]arene with N-(2-hydroxyethyl)phthalimide and the reduction of a O,O'-disiloxanediyl-bridged O",O"'-bis(cyanomethyl) ether of 1,2-alternate conformation, respectively. These products are expected to serve as useful precursors of highly elaborated synthetic receptors, including biscalixarenes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.035
• 作为产物：
  描述：

  氯乙腈 、 4-叔丁基硫杂杯[4]芳烃 在 caesium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 168.0h， 以70%的产率得到5,11,17,23-tetra-tert-butyl-25,27-bis(cyanomethoxy)-26,28-dihydroxythiacalix[4]arene
  参考文献：
  名称：

  Interconversion betweensynandantiConformations of 1,3-Bis(O-cyanomethyl)-p-tert-butylthiacalix[4]arene

  摘要：

  已发现 1,3-双(O-氰甲基)-对叔丁基硫杂萼[4]芳烃 (5) 在溶液中可在顺式构象和反式构象之间相互转化。随着溶剂极性的增加，平衡向反态移动。在固态时，它采用氰甲基顺式排列的收缩锥构象。用LiAlH 4 还原5的平衡混合物仅得到1,3-双(O-氨基乙基)-对叔丁基硫杂杯[4]芳烃的反式立体异构体。

  DOI：

  10.1246/cl.2004.184

文献信息

• Stereoselective synthesis of all stereoisomers of vicinal and distal bis(O-2-aminoethyl)-p-tert-butylthiacalix[4]arene
  作者：Vandana Bhalla、Manoj Kumar、Tetsutaro Hattori、Sotaro Miyano

  DOI：10.1016/j.tet.2004.05.035

  日期：2004.7

  O,O"- and O,O'-bis(2-aminoethyl)-p-tert-butylthiacalix[4]arenes of anti conformation have been prepared by the reduction of the corresponding O,O"- and O,O'-bis(cyanomethyl) ethers. Their syn-O,O"- and O,O'-counterparts have been prepared by alternative routes via the Mitsunobu reaction of thiacalix[4]arene with N-(2-hydroxyethyl)phthalimide and the reduction of a O,O'-disiloxanediyl-bridged O",O"'-bis(cyanomethyl) ether of 1,2-alternate conformation, respectively. These products are expected to serve as useful precursors of highly elaborated synthetic receptors, including biscalixarenes. (C) 2004 Elsevier Ltd. All rights reserved.
• Interconversion between<i>syn</i>and<i>anti</i>Conformations of 1,3-Bis(<i>O</i>-cyanomethyl)-<i>p</i>-<i>tert</i>-butylthiacalix[4]arene
  作者：Vandana Bhalla、Manoj Kumar、Chizuko Kabuto、Tetsutaro Hattori、Sotaro Miyano

  DOI：10.1246/cl.2004.184

  日期：2004.2

  1,3-Bis(O-cyanomethyl)-p-tert-butylthiacalix[4]arene (5) has been found to interconvert between syn and anti conformations in solution. The equilibrium shifts toward the anti form with increasing solvent polarity. In the solid state, it adopts a pinched cone conformation with the syn arrangement of the cyanomethyl groups. Reduction of the equilibrium mixture of 5 with LiAlH4 gives only anti stereoisomer of 1,3-bis(O-aminoethyl)-p-tert-butylthiacalix[4]arene.

  已发现 1,3-双(O-氰甲基)-对叔丁基硫杂萼[4]芳烃 (5) 在溶液中可在顺式构象和反式构象之间相互转化。随着溶剂极性的增加，平衡向反态移动。在固态时，它采用氰甲基顺式排列的收缩锥构象。用LiAlH 4 还原5的平衡混合物仅得到1,3-双(O-氨基乙基)-对叔丁基硫杂杯[4]芳烃的反式立体异构体。