10,10-dioxo-5H-5λ⁴,10λ⁶-thianthren-5-ylideneamine | 321331-65-1

• 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: 10,10-dioxo-5H-5λ⁴,10λ⁶-thianthren-5-ylideneamine
• 英文别名: 5-iminothianthrene 10,10-dioxide；10-Dioxy-5-iminothianthrene；10-Iminothianthrene 5,5-dioxide
• CAS: 321331-65-1
• 化学式: C₁₂H₉NO₂S₂
• 分子量: 263.341
• InChiKey: GZFDTIUWLNXIQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 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：
  85.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10,10-dioxo-5H-5λ⁴,10λ⁶-thianthren-5-ylideneamine 在 硫酸 作用下， 反应 3.0h， 以95%的产率得到thianthrene-5,5,10-trioxide
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1002/1521-3765(20001103)6:21<3976::aid-chem3976>3.0.co;2-5
• 作为产物：
  描述：

  噻蒽 在 硫酸 、 水 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 10,10-dioxo-5H-5λ⁴,10λ⁶-thianthren-5-ylideneamine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

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

文献信息

• A new method for the preparation of fluoro-λ6-sulfanenitriles: reaction of sulfimides with Selectfluor™
  作者：Takayoshi Fujii、Shinsuke Asai、Tomoyuki Okada、Wei Hao、Hiroyuki Morita、Toshiaki Yoshimura

  DOI：10.1016/s0040-4039(03)01547-8

  日期：2003.8

  Several diaryl(fluoro)-λ6-sulfanenitriles 3 were synthesized by the reaction of S,S-diarylsulfimides 1 with Selectfluor™. This reaction also allows the first preparation of heterocyclic fluoro-λ6-sulfanenitrile, 5-fluoro-10,10-dioxo-5,10-dihydro-5λ6,10λ6-thianthren-5-nitrile (5) and its molecular structure was determined by X-ray crystallographic analysis.

  几个芳基（氟）-λ 6 -sulfanenitriles 3由反应合成小号，小号-diarylsulfimides 1与的Selectfluor™。该反应也允许杂环氟λ的第一准备6 -sulfanenitrile，5-氟-10,10-二氧代-5,10-二氢5λ 6，10λ 6 -thianthren -5-腈（5）和其分子结构通过X射线晶体学分析确定。
• 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.