2-methyl-3-((4-nitrophenyl)thio)-1H-indole | 1210054-39-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methyl-3-((4-nitrophenyl)thio)-1H-indole
• 英文别名: 2-methyl-3-(4-nitrophenyl)sulfanyl-1H-indole
• CAS: 1210054-39-9
• 化学式: C₁₅H₁₂N₂O₂S
• 分子量: 284.338
• InChiKey: ITIQZHNNHFCMPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  86.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-nitrophenylthio)morpholine 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 4.17h， 生成 2-methyl-3-((4-nitrophenyl)thio)-1H-indole
  参考文献：
  名称：

  在氧氯化磷（V）存在下用芳基亚磺酰胺进行杂环化合物的芳基亚磺酰化

  摘要：

  研究了在存在卤化磷（V）的情况下，一系列的吲哚和吡咯与芳基亚磺酰胺的亲电子亚磺酰化反应。已经显示，吲哚的芳基亚磺酰基化导致产物在3位被取代，而在吡咯的情况下，它发生在2位。

  DOI：

  10.1007/s10593-010-0629-4

文献信息

• A Metal-Free Sulfenylation and Bromosulfenylation of Indoles: Controllable Synthesis of 3-Arylthioindoles and 2-Bromo-3-arylthioindoles
  作者：Dayun Huang、Jiuxi Chen、Weixing Dan、Jinchang Ding、Miaochang Liu、Huayue Wu

  DOI：10.1002/adsc.201200227

  日期：2012.8.13

  An efficient metal-free sulfenylation of indoles with disulfides has been developed, leading to 3-arylthioindoles in moderate to excellent yields. Furthermore, bromosulfenylation of indoles with disulfides has been realized for the first time providing a new family of 2-bromo-3-arylthioindole derivatives in good yield by the one-pot construction of CS and CBr bonds. It is noteworthy that the system

  已经开发出吲哚与二硫化物的有效的无金属的亚磺酰基化，导致3-芳基硫代吲哚的产率中等至优异。此外，通过二硫键的一锅法构建，首次实现了吲哚的二硫代溴亚磺酰化，以高收率提供了新的2-溴-3-芳基硫代吲哚衍生物新家族。值得注意的是，该系统支持在RSSR中同时使用两个RS部分，并显示出广泛的功能基团耐受性。
• Iron-Catalyzed Sulfenylation of Indoles with Disulfides Promoted by a Catalytic Amount of Iodine
  作者：Jin-Heng Li、Xiao-Li Fang、Ri-Yuan Tang、Ping Zhong

  DOI：10.1055/s-0029-1217037

  日期：——

  Selective sulfenylation of indoles with disulfides using iron(III) fluoride combined with iodine has been developed for the synthesis of sulfenylindoles. In the presence of iron(III) fluoride and iodine, a variety of disulfides underwent the reaction with indoles selectively to afford the corresponding sulfenylindoles in good to excellent yields. Moreover, reactions of indoles with 1,2-diphenyldiselane were also conducted under the same conditions, which smoothly afforded 3-selenylindoles in good yields.

  利用氟化铁（III）和碘，开发了吲哚与二硫化物的选择性亚硫酰化反应，用于合成亚磺酰基吲哚。在氟化铁（III）和碘的存在下，多种二硫化物与吲哚发生选择性反应，生成相应的亚磺酰基吲哚，收率从良好到极佳。此外，在相同的条件下，吲哚与 1,2-二苯基二硒烷也发生了反应，并以良好的收率顺利得到了 3-硒基吲哚。
• Electrochemical Sulfenylation of Indoles with Disulfides Mediated by Potassium Iodide
  作者：Chen Chen、Pengfei Niu、Zhenlu Shen、Meichao Li

  DOI：10.1149/2.0071807jes

  日期：——

  A novel electrochemical system for sulfenylation of indoles with disulfides to generate 3-sulfenylindoles via C-S bond formation mediated by potassium iodide at a low potential was developed. Iodine was electrogenerated from iodide ions at a graphite anode and showed a high catalytic activity for the electrochemical sulfenylation reactions. A variety of aromatic, heteroaromatic and aliphatic disulfides could react with 2-methlyindole to synthesize the corresponding 3-sulfenylindoles in good to excellent yields. In addition, protected and unprotected indoles with various groups, especially electron-donating groups, also performed well in the sulfenylation reactions. The transformation, which proceeded through the redox of iodine and the generation of intermediate 3-iodoindole, provided an efficient and environmentally benign protocol for the synthesis of 3-sulfenylindoles under mild conditions. (C) 2018 The Electrochemical Society.
• Silver-Mediated Sulfenylation of Indoles and Benzimidazoles with Di(hetero)aryl Disulfides
  作者：Xi-Cun Wang、Wen-Juan Wang

  DOI：10.3987/com-16-13641

  日期：——

  An efficient synthesis of novel sulfenylated N-heterocycles derivatives via AgNO3 mediated C-S coupling reaction has been developed. This reaction could be carried out under mild reaction conditions with straightforward operation and good yield. A wide range of substrates can be utilized for the C-S coupling reaction giving sulfenylated indoles and benzimidazoles, which are the importance of frameworks in medicinal and synthetic chemistry.