4,6,11,13,18,20,25,27-Octamethyl<2.2.2.2>(3,4)thiophenophane | 273738-31-1

• 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: 4,6,11,13,18,20,25,27-Octamethyl<2.2.2.2>(3,4)thiophenophane
• 英文别名: 4,6,11,13,18,20,25,27-Octamethyl[2.2.2.2](3,4)thiophenophane；5,7,12,14,19,21,26,28-Octamethyl-6,13,20,27-tetrathiapentacyclo[23.3.0.04,8.011,15.018,22]octacosa-1(28),4,7,11,14,18,21,25-octaene
• CAS: 273738-31-1
• 化学式: C₃₂H₄₀S₄
• 分子量: 552.934
• InChiKey: BVBJHSMZBPLMJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  36
• 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：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6,11,13,18,20,25,27-Octamethyl<2.2.2.2>(3,4)thiophenophane 、 丁炔二酸二甲酯 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到1,4,7,10,13,16,19,22-Octamethyl-5,6,11,12,17,18,23,24-octahydro-tetrabenzo[a,e,i,m]cyclohexadecen-2,3,8,9,14,15,20,21-octacarboxylic acid octamethyl ester
  参考文献：
  名称：

  Oxidative Cycloaddition of Molecules with Multiple Thiophene Cores

  摘要：

  DOI：

  10.3987/com-99-s134
• 作为产物：
  描述：

  噻吩-2-碳酸酯 在 lithium 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 16.0h， 生成 4,6,11,13,18,20,25,27-Octamethyl<2.2.2.2>(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

文献信息

• Oxidative Cycloaddition of Molecules with Multiple Thiophene Cores
  作者：Shuntaro Mataka、Thies Thiemann、Yuanqiang Li、Carolin Thiemann、Tsuyoshi Sawada、Daisuke Ohira、Masashi Tashiro

  DOI：10.3987/com-99-s134

  日期：——
• Synthesis and structure of [24](2,3,4,5)-thiophenophane (superthiophenophane)
  作者：Michinori Takeshita、Masanori Koike、Hirohisa Tsuzuki、Masashi Tashiro

  DOI：10.1021/jo00043a023

  日期：1992.8

  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.