5-imino-5H-5λ⁴-thianthrene 5-oxide | 54001-95-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-imino-5H-5λ⁴-thianthrene 5-oxide
• 英文别名: 5-Iminothianthrene 5-oxide
• CAS: 54001-95-5
• 化学式: C₁₂H₉NOS₂
• 分子量: 247.342
• InChiKey: CVOFUVKBXLIIGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 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：
  74.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-imino-5H-5λ⁴-thianthrene 5-oxide 、 溴甲苯 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以89%的产率得到
  参考文献：
  名称：

  NH-亚砜肟的光催化N-苄基化

  摘要：

  摘要 通过可见光光催化实现了NH-亚磺酰亚胺的N-苄基化。下温和的反应条件下，光催化剂促进的直接交叉偶联NH与苄基溴-sulfoximines以形成Ñ -benzylation亚磺酰亚胺。这项工作不需要通常用于报道的NH-磺胺嘧啶与烷基卤的偶合的超强碱。该方法也适合于合成N-烯丙基硫代亚砜。

  DOI：

  10.1080/00397911.2021.1883664
• 作为产物：
  描述：

  5-iminothianthrene 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 2.25h， 生成 5-imino-5H-5λ⁴-thianthrene 5-oxide
  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

• Rhodium-Catalyzed Enantioselective N-Allylation of Sulfoximines
  作者：Yang-yang Li、Bing Gao

  DOI：10.1021/acs.orglett.3c00414

  日期：2023.4.28

  The N-functionalization of free sulfoximines is an important approach to modifying their chemical and biological properties for downstream applications. Here, we report a rhodium-catalyzed N-allylation of free sulfoximines (═NH) with allenes under mild conditions. The redox-neutral and base-free process enables chemo- and enantioselective γ-hydroamination of allenes and gem-difluoroallenes. Synthetic

  游离亚砜亚胺的N-功能化是为下游应用改变其化学和生物学特性的重要方法。在这里，我们报道了在温和条件下，铑催化的游离亚砜亚胺 (=NH) 与丙二烯的N-烯丙基化反应。氧化还原中性和无碱工艺可实现丙二烯和偕二氟丙二烯的化学和对映选择性 γ-加氢胺化。已经证明了由此获得的亚砜亚胺产物的合成应用。
• Electrochemical <i>N</i>‐Aroylation of Sulfoximines by Using Benzoyl Hydrazines with H₂ Generation
  作者：Tipu Alam、Bhisma K. Patel

  DOI：10.1002/chem.202303444

  日期：2024.2.12

  Developed here is a robust electrochemical cross‐coupling reaction between aroyl hydrazine and NH‐sulfoximine via concomitant cleavage and formation of C(sp²)−N bonds with the evolution of H₂ and N₂ as innocuous by‐products. This sustainable protocol avoids the use of toxic reagents and occurs at room temperature. The reaction proceeds via the generation of an aroyl and a sulfoximidoyl radical via anodic oxidation under constant current electrolysis (CCE), affording N‐aroylated sulfoximine. The strategy is applied to late‐stage sulfoximidation of L‐menthol, (−)‐borneol, D‐glucose, vitamin‐E derivatives, and marketed drugs such as probenecid, ibuprofen, flurbiprofen, ciprofibrate, and sulindac. In addition, the present methodology is mild, high functional group tolerance with broad substrate scope and scalable.

  摘要 本研究开发了芳基肼和 NH-亚磺酰亚胺之间的强效电化学交叉偶联反应，该反应通过同时裂解和形成 C（sp2）-N 键，并生成无害的副产物 H2 和 N2。这种可持续的方案避免了有毒试剂的使用，并可在室温下进行。反应在恒流电解（CCE）条件下通过阳极氧化生成一个芳酰基和一个亚磺酰亚胺基，从而得到 N-芳酰基亚磺酰亚胺。该策略适用于 L-薄荷醇、(-)-薄荷醇、D-葡萄糖、维生素-E 衍生物以及丙磺舒、布洛芬、氟比洛芬、环丙沙星和舒林酸等市售药物的后期硫代氧化。此外，本方法性质温和、对官能团的耐受性高、底物范围广且可扩展。