5,7,13,15-Tetramethyl-2,10-dithia<3.3>(3,4)thiophenophane | 40953-55-7

• 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: 5,7,13,15-Tetramethyl-2,10-dithia<3.3>(3,4)thiophenophane
• 英文别名: 6,8,14,16-Tetramethyl-3,7,11,15-tetrathiatricyclo[11.3.0.05,9]hexadeca-1(16),5,8,13-tetraene
• CAS: 40953-55-7
• 化学式: C₁₆H₂₀S₄
• 分子量: 340.599
• InChiKey: IFZAEMIJUCHJAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• 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：

  5,7,13,15-Tetramethyl-2,10-dithia<3.3>(3,4)thiophenophane 在 N-溴代丁二酰亚胺(NBS) 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 25.0~550.0 ℃ 、133.32 Pa 条件下， 反应 18.0h， 生成 4,6,11,13-Tetrakis(bromomethyl)<2.2>(3,4)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
• 作为产物：
  描述：

  噻吩-2-碳酸酯 在 氢氧化钾 、 sodium tetrahydroborate 、 硫脲 作用下， 以 乙醇 、 苯 为溶剂， 反应 24.0h， 生成 5,7,13,15-Tetramethyl-2,10-dithia<3.3>(3,4)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