5-iminothianthrene | 35566-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二硫类化合物
• 英文名称: 5-iminothianthrene
• CAS: 35566-32-6
• 化学式: C₁₂H₉NS₂
• 分子量: 231.342
• InChiKey: RTLAQZILLORCIR-UHFFFAOYSA-N

物化性质

• 沸点：
  401.7±38.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-iminothianthrene 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到噻蒽
  参考文献：
  名称：

  Photo SN-bond cleavage and related reactions of thianthrene sulfilimine derivatives

  摘要：

  Several 1- and 2-substituted thianthrene sulfilimine derivatives were prepared and the selectivity toward oxidation and N-tosylimination under several conditions was studied. In the photolysis of trans-5-(N-p-tosyl) iminothianthrene 10-oxide (trans-10), photo isomerization to cis-10 was observed. Further, photoimino-transferreaction of sulfilimines and their 10-mono- and -dioxide derivatives to sulfides was intensively studied to make clear the ability as nitrene precursors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.004
• 作为产物：
  描述：

  噻蒽 在 O-(2,4,6-三甲基苯磺酰基)乙酰羟肟酸乙酯 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以76%的产率得到5-iminothianthrene
  参考文献：
  名称：

  Alkaline hydrolysis of N-bromoiminothianthrene derivatives

  摘要：

  5-(N-Bromo)iminothianthrene (2) and 5-(N-bromo)iminothianthrene 10-oxide (5) and 10,10-dioxide (8) were prepared and their alkaline hydrolyses were studied. The compound 2 and cis-5-(N-bromo)iminothianthrene 10-oxide (cis-5) afforded the corresponding sulfoximine exclusively. While, unexpectedly, both trans-5-(N-bromo)iminothianthrene 10-oxide (trans-5) and 8 afforded mainly de-brominated products, trans-5-iminothianthrene 10-oxide (trans-4) and 5-iminothianthrene 10,10-dioxide (7), respectively. In these cases, 5-iminothianthrene 5, 10-dioxide (6) (Z- and E-mixture) and 5-iminothianthrene 5, 10, 1 0-trioxide (9) and further de-iminated products were also formed respectively as minor products. The stereochemical considerations on the S-N reactions are described in view of the steric effect and 'flip-flap' motion of the thianthrene framework. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.087

文献信息

• Migrative Thioamination of Aryne Intermediates Generated from o-Iodoaryl Triflates
  作者：Suguru Yoshida、Shinya Tabata、Mai Minoshima、Akihiro Kobayashi、Takamitsu Hosoya

  DOI：10.1055/a-2030-6299

  日期：——

  takes place using various o-iodoaryl triflates and sulfilimines. The selective migration realizes the facile synthesis of a broad range of highly functionalized o-thioaminated diaryl sulfides. We succeeded in the ring expansion of cyclic sulfilimines enabling us to prepare eight- and nine-membered organosulfurs from dibenzothiophene- and thianthrene-type sulfilimines, respectively.

  使用各种邻碘芳基三氟甲磺酸酯和硫亚胺发生芳炔中间体的迁移硫胺化。选择性迁移实现了范围广泛的高度功能化的邻硫胺化二芳基硫化物的简便合成。我们成功地进行了环状硫亚胺的扩环，使我们能够分别从二苯并噻吩型和噻蒽型硫亚胺制备八元和九元有机硫。