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.
• Arylsulfenylation of heterocyclic compounds with arylsulfenamides in the presence of phosphorus(V) oxochloride
  作者：R. L. Antipin、A. N. Chernysheva、E. K. Beloglazkina、N. V. Zyk

  DOI：10.1007/s10593-010-0629-4

  日期：2010.12

  The electrophilic sulfenylation of a series of indoles and pyrroles with arylsulfenamides in the presence of phophorus(V) oxohalide has been studied. It has been shown that arylsulfenylation of indoles led to products with substitution at position 3, while in the case of pyrrole it occurred at position 2.

  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。