5-(N-p-Toluenesulfonyl)iminothianthrene | 19615-38-4

• 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-(N-p-Toluenesulfonyl)iminothianthrene
• 英文别名: 5-(N-p-tosyl)iminothianthrene；4-methyl-N-thianthren-5-ylidenebenzenesulfonamide
• CAS: 19615-38-4
• 化学式: C₁₉H₁₅NO₂S₃
• 分子量: 385.532
• InChiKey: YQTSDQSVJKPMCS-UHFFFAOYSA-N

物化性质

• 沸点：
  595.2±53.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(N-p-Toluenesulfonyl)iminothianthrene 在 1,4-二溴丁烷 、 锌 作用下， 反应 2.0h， 以40%的产率得到噻蒽
  参考文献：
  名称：

  Nagasawa, Kazuo; Yoneta, Akemi; Sugimoto, Hideki, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 10, p. 4351 - 4354

  摘要：

  DOI：
• 作为产物：
  描述：

  trans-5-(N-p-tosyl)iminothianthrene 10-oxide 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 生成 5-(N-p-Toluenesulfonyl)iminothianthrene
  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

文献信息

• Syntheses and Structural Analysis of 10-Monoxy- and -Dioxy-5-N-Substituted Iminothianthrene Derivatives and the Stereochemical Change on their Sulfur Atom under Acidic and Thermal Conditions
  作者：Hiroyuki Morita、Hiroyuki Kawaguchi、Toshiaki Yoshimura、Eiichi Tsukurimichi、Choichiro Shimasaki、Ernst Horn

  DOI：10.1002/1521-3765(20001103)6:21<3976::aid-chem3976>3.0.co;2-5

  日期：2000.11.3

  5-(N-p-Tolulnesulfonyl)iminothianthrenes, whose sulfur atoms are oxidized to a sulfoxide or sulfone at the 10-position. were hydrolysed readily in high yield to N-unsubstituted-suifilimines by using concentrated H2SO4. During hydrolysis, 10-monoxy-5-N-unsubstituted-sulfilimines were obtained as a separable mixture of the cis and trims isomers. The stereochemical interconversion of these compounds was studied under both hydrolytic and thermal conditions and their structures were elucidated by using X-ray crystallography.
• Alkaline hydrolysis of N-bromoiminothianthrene derivatives
  作者：Hiroyuki Kawaguchi、Akitaka Nakajima、Takayoshi Fujii、Bung Ju Kim、Junko Hashimoto、Akihiro Fujimoto、Toshiaki Yoshimura、Hiroyuki Morita

  DOI：10.1016/j.tet.2006.08.087

  日期：2006.11

  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.