rac-4-bromo-25,26,27,28-tetrapropoxythiacalix[4]arene | 1628434-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: rac-4-bromo-25,26,27,28-tetrapropoxythiacalix[4]arene
• 英文别名: 4-bromo-25,26,27,28-tetrapropoxythiacalix[4]arene；4-Bromo-25,26,27,28-tetrapropoxy-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-dodecaene；4-bromo-25,26,27,28-tetrapropoxy-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-dodecaene
• CAS: 1628434-02-5；1628434-09-2
• 化学式: C₃₆H₃₉BrO₄S₄
• 分子量: 743.871
• InChiKey: YIOUXMAVQUETLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  25,26,27,28-tetrapropoxy-2,8,14,20-tetrathiacalix[4]arene 在 N-溴代丁二酰亚胺(NBS) 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以56%的产率得到rac-4-bromo-25,26,27,28-tetrapropoxythiacalix[4]arene
  参考文献：
  名称：

  Regioselective Halogenation of Thiacalix[4]arenes in the Cone and 1,3-Alternate Conformations

  摘要：

  Monohalogenation of thiacalix[4]arene in the cone conformation gave either the meta- or para-substituted isomers depending on the halogen and reaction conditions used. Surprisingly, the same reaction with the 1,3-alternate conformer led only to the meta isomer. This is the first example of such a conformation-dependent regioselectivity in calixarene/thiacalixarene chemistry. As the halogen-substituted calixarenes are useful synthetic intermediates, this provided the unique opportunity to functionalize the basic skeleton at two different positions.

  DOI：

  10.1021/ol5024536

文献信息

• Mercuration of thiacalix[4]arenes in the cone and 1,3-alternate conformations
  作者：F. Botha、S. Böhm、H. Dvořáková、V. Eigner、P. Lhoták

  DOI：10.1039/c4ob00799a

  日期：——

  respectively. The organomercurial intermediates show unusual solid-state behaviour, as evidenced by the formation of η6 complexes, and can be easily transformed into halogen-substituted derivatives, so far inaccessible in thiacalixarene chemistry. This paves the way towards the synthesis of inherently chiral thiacalixarene-based receptors with an unusual substitution pattern.

  使用固定在视锥或1,3-交替构象上的噻唑并[4]芳烃在噻唑并芳烃系列中进行的第一次汞键转化，得到了两种单体固化的区域异构体（间位和对位）的混合物。分别为4：1和2：1的比率。的有机汞中间体显示不寻常的固态行为，如通过η的形成证实6种复合物，并且能够容易地转化为卤素取代的衍生物，迄今为止不可访问在硫杂杯芳烃的化学反应。这为合成具有不寻常取代模式的手性噻th草芳基受体铺平了道路。
• Regioselective Halogenation of Thiacalix[4]arenes in the <i>Cone</i> and <i>1,3-Alternate</i> Conformations
  作者：Jan Lukášek、Stanislav Böhm、Hana Dvořáková、Václav Eigner、Pavel Lhoták

  DOI：10.1021/ol5024536

  日期：2014.10.3

  Monohalogenation of thiacalix[4]arene in the cone conformation gave either the meta- or para-substituted isomers depending on the halogen and reaction conditions used. Surprisingly, the same reaction with the 1,3-alternate conformer led only to the meta isomer. This is the first example of such a conformation-dependent regioselectivity in calixarene/thiacalixarene chemistry. As the halogen-substituted calixarenes are useful synthetic intermediates, this provided the unique opportunity to functionalize the basic skeleton at two different positions.