3,4-bis(mercaptomethyl)-2,5-dimethylthiophene | 699-94-5

• 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: 3,4-bis(mercaptomethyl)-2,5-dimethylthiophene
• 英文别名: 2,5-Dimethyl-3,4-bis(mercaptomethyl)thiophene；2,5-Dimethyl-3,4-thiophenedimethanethiol；[2,5-dimethyl-4-(sulfanylmethyl)thiophen-3-yl]methanethiol
• CAS: 699-94-5
• 化学式: C₈H₁₂S₃
• 分子量: 204.381
• InChiKey: QSIYYHDCRSNAAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-bis(mercaptomethyl)-2,5-dimethylthiophene 在 氢氧化钾 、 sodium tetrahydroborate 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 生成 6,8-Dimethyl-3,7,11-trithia-tricyclo[11.3.1.0^5,9]heptadeca-1(16),5,8,13(17),14-pentaene 3,3,11,11-tetraoxide
  参考文献：
  名称：

  Synthesis and conformation of dithia[3]metacyclo[3]thiophenophanes and [2]metacyclo[2]thiophenophanes

  摘要：

  Dithia[3]metacyclo[3]- -(2,3)-, -(2,4)-, -(2,5)-, and -(3,4)thiophenophanes were prepared by dithiol bis-alkylations and were oxidized with m-chloroperbenzoic acid to the corresponding tetraoxides. Pyrolysis of the tetraoxides under a reduced pressure gave the corresponding [2]metacyclo[2]thiophenophanes together with many unexpected compounds. The conformations of the obtained products are also discussed.

  DOI：

  10.1021/jo00008a046
• 作为产物：
  描述：

  2,5-二甲基噻吩 在 sodium hydroxide 、 磷酸 、 硫脲 作用下， 以 溶剂黄146 为溶剂， 生成 3,4-bis(mercaptomethyl)-2,5-dimethylthiophene
  参考文献：
  名称：

  Synthesis and conformation of dithia[3]metacyclo[3]thiophenophanes and [2]metacyclo[2]thiophenophanes

  摘要：

  Dithia[3]metacyclo[3]- -(2,3)-, -(2,4)-, -(2,5)-, and -(3,4)thiophenophanes were prepared by dithiol bis-alkylations and were oxidized with m-chloroperbenzoic acid to the corresponding tetraoxides. Pyrolysis of the tetraoxides under a reduced pressure gave the corresponding [2]metacyclo[2]thiophenophanes together with many unexpected compounds. The conformations of the obtained products are also discussed.

  DOI：

  10.1021/jo00008a046

文献信息

• 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.