2,10-Dithia<3.2.2.3>(2,3,4,5)thiophenophane | 142564-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2,10-Dithia<3.2.2.3>(2,3,4,5)thiophenophane
• 英文别名: 2,10-Dithia[3.2.2.3](2,3,4,5)thiophenophane；3,6,9,20-Tetrathiapentacyclo[9.8.1.05,16.07,15.012,19]icosa-1(19),5(16),7(15),11-tetraene
• CAS: 142564-45-2
• 化学式: C₁₆H₁₆S₄
• 分子量: 336.567
• InChiKey: NEQOSPYCTOGHKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,10-Dithia<3.2.2.3>(2,3,4,5)thiophenophane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以68%的产率得到2,10-Dithia<3.2.2.3>(2,3,4,5)thiophenophane 2,2,10,10-tetraoxide
  参考文献：
  名称：

  Synthesis and structure of [24](2,3,4,5)-thiophenophane (superthiophenophane)

  摘要：

  The synthesis of [2(4)](2,3,4,5)thiophenophane (superthiophenophane) (1), the first 'ultimate' heterophane, was accomplished in five steps from 3,4-bis(chloromethyl)-2,5-dimethylthiophene. In the respective C-13 NMR spectra, the signals due to the thiophene ring carbons of 1 appear at lower field than do those of the carbons of 2,10-dithia[3.2.2.3](2,3,4,5)thiophenophane (5). This shift is elucidated as a compression effect between facial p-orbitals of the thiophene carbons. The UV spectra of the two thiophenophanes are, however, almost identical. The results of X-ray crystallographic analysis show that 1 is a more strained molecule than 5.

  DOI：

  10.1021/jo00043a023
• 作为产物：
  描述：

  噻吩-2-碳酸酯 在 sodium sulfide 、 氢氧化钾 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 硫脲 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 25.0~550.0 ℃ 、133.32 Pa 条件下， 反应 78.0h， 生成 2,10-Dithia<3.2.2.3>(2,3,4,5)thiophenophane
  参考文献：
  名称：

  Synthesis and structure of [24](2,3,4,5)-thiophenophane (superthiophenophane)

  摘要：

  The synthesis of [2(4)](2,3,4,5)thiophenophane (superthiophenophane) (1), the first 'ultimate' heterophane, was accomplished in five steps from 3,4-bis(chloromethyl)-2,5-dimethylthiophene. In the respective C-13 NMR spectra, the signals due to the thiophene ring carbons of 1 appear at lower field than do those of the carbons of 2,10-dithia[3.2.2.3](2,3,4,5)thiophenophane (5). This shift is elucidated as a compression effect between facial p-orbitals of the thiophene carbons. The UV spectra of the two thiophenophanes are, however, almost identical. The results of X-ray crystallographic analysis show that 1 is a more strained molecule than 5.

  DOI：

  10.1021/jo00043a023