2-(4-bromophenyl)-2-(4-iodophenyl)-[1,3]dithiolane | 866393-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-bromophenyl)-2-(4-iodophenyl)-[1,3]dithiolane
• 英文别名: 2-(4-bromophenyl)-2-(4-iodophenyl)-1,3-dithiolane
• CAS: 866393-58-0
• 化学式: C₁₅H₁₂BrIS₂
• 分子量: 463.201
• InChiKey: KMQRKWFBCXVLEK-UHFFFAOYSA-N

物化性质

• 沸点：
  484.2±45.0 °C(Predicted)
• 密度：
  1.832±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)-2-(4-iodophenyl)-[1,3]dithiolane 在 copper(l) iodide bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 22.0h， 生成 3,4-bis[4-(2-{4-[(triisopropylsilylethynyl)ethynyl]phenyl}-[1,3]dithiolan-2-yl)phenyl]-2,5-diphenylcyclopentadienone
  参考文献：
  名称：

  Multiple Functionalization of Benzophenones Inside Polyphenylene Dendrimers − Toward Entrapped Ions and Radicals

  摘要：

  Polyphenylene dendrimers possessing a defined number of keto groups in the dendritic scaffold have been synthesized by using a benzophenone-functionalized tetraphenylcyclopentadienone branching unit. A postsynthetic functionalization of the polyphenylene backbone was achieved by reacting the entrapped keto groups with organolithium reagents yielding monodisperse alcohol products. To investigate the accessibility and reactivity of the embedded groups, many functions of different size and nature, for example, the chromophore pyrene, were introduced. Moreover, suitable precursors for the synthesis of dendrimer entrapped species, trityl cations, trityl radicals, and ketyl radical anions, were obtained. To gain insight into the structure of these newly functionalized dendrimers, UV/vis, EPR, and NMR measurements have been performed. They showed a delocalization of the charge/spin into the polyphenylene dendritic arms leading to a stabilization of the ions/radicals. Remarkably, for the ketyl radicals, EPR measurements indicated the occurrence of intermolecular metal-bridged biradicals. They suggest the existence of a dendritic radical network of the dendrimers themselves.

  DOI：

  10.1021/ja052856f
• 作为产物：
  描述：

  (4-bromophenyl)-(4-iodophenyl)methanol 在 草酰氯 、 BF₃*Ac₂O 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-(4-bromophenyl)-2-(4-iodophenyl)-[1,3]dithiolane
  参考文献：
  名称：

  Multiple Functionalization of Benzophenones Inside Polyphenylene Dendrimers − Toward Entrapped Ions and Radicals

  摘要：

  Polyphenylene dendrimers possessing a defined number of keto groups in the dendritic scaffold have been synthesized by using a benzophenone-functionalized tetraphenylcyclopentadienone branching unit. A postsynthetic functionalization of the polyphenylene backbone was achieved by reacting the entrapped keto groups with organolithium reagents yielding monodisperse alcohol products. To investigate the accessibility and reactivity of the embedded groups, many functions of different size and nature, for example, the chromophore pyrene, were introduced. Moreover, suitable precursors for the synthesis of dendrimer entrapped species, trityl cations, trityl radicals, and ketyl radical anions, were obtained. To gain insight into the structure of these newly functionalized dendrimers, UV/vis, EPR, and NMR measurements have been performed. They showed a delocalization of the charge/spin into the polyphenylene dendritic arms leading to a stabilization of the ions/radicals. Remarkably, for the ketyl radicals, EPR measurements indicated the occurrence of intermolecular metal-bridged biradicals. They suggest the existence of a dendritic radical network of the dendrimers themselves.

  DOI：

  10.1021/ja052856f