1-methyl-2-(phenylsulfanyl)-1H-indole | 120517-32-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-methyl-2-(phenylsulfanyl)-1H-indole
• 英文别名: 1-methyl-2-(phenylthio)-1H-indole；1-methyl-2-(phenylthio)indole；1-Methyl-2-phenylsulfanylindole
• CAS: 120517-32-0
• 化学式: C₁₅H₁₃NS
• 分子量: 239.341
• InChiKey: RHUNAQRLIUERGA-UHFFFAOYSA-N

物化性质

• 熔点：
  71-73 °C
• 沸点：
  412.3±18.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 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：
  30.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-methyl-2,3-bis(phenylthio)indole 在 三氟乙酸 作用下， 反应 18.0h， 以86%的产率得到1-methyl-2-(phenylsulfanyl)-1H-indole
  参考文献：
  名称：

  吲哚-3-基硫化物的酸催化异构化为吲哚-2-基硫化物：重排的意想不到的分子间性质

  摘要：

  质子酸催化的吲哚-3-基硫醚（1）重排为吲哚-2-基硫醚（4），是通过分子间机理意外地进行的，该分子间机理涉及初始歧化成吲哚-2,3-二烷基二硫化物（2）和吲哚（3），然后（2）和（3）之间反应，得到重排产物（4）。

  DOI：

  10.1039/c39890000063

文献信息

• TFA-promoted direct C–H sulfenylation at the C2 position of non-protected indoles
  作者：Thomas Hostier、Vincent Ferey、Gino Ricci、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1039/c5cc05421d

  日期：——

  An efficient metal-free C–H sulfenylation process at the C2 position of non-protected indoles has been developed.

  一种高效的无金属C-H砜基化过程已经在非保护吲哚的C2位置上开发出来。
• Switchable regioselection of C–H thiolation of indoles using different TMS counterions
  作者：Yuan-Zhao Ji、Hui-Jing Li、Jin-Yu Zhang、Yan-Chao Wu

  DOI：10.1039/c9cc05652a

  日期：——

  Simply swapping the counteranions of TMS leads to a switchable regioselectivity in C2– and C3–H thiolation of indoles.

  将TMS的对阴离子简单交换可在吲哚的C2和C3-H硫化中导致可切换的区域选择性。
• Benzoic Acid-Promoted C2–H Borylation of Indoles with Pinacolborane
  作者：Youliang Zou、Binfeng Zhang、Li Wang、Hua Zhang

  DOI：10.1021/acs.orglett.1c00809

  日期：2021.4.2

  A benzoic acid-promoted C2–H borylation of indoles with pinacolborane to afford C2-borylated indoles is developed. Preliminary mechanistic studies indicate BH3-related borane species formed via the decomposition of pinacolborane to be the probable catalyst. This transformation provides a prompt route toward the synthesis of diverse C2-functionalized indoles.

  已开发出苯甲酸与频哪醇硼烷一起促进吲哚的C2-H硼酸酯化，以提供C2硼化的吲哚。初步的机理研究表明，通过频哪醇硼烷的分解形成的BH 3相关的硼烷物质可能是催化剂。这种转变为合成各种C2功能化的吲哚提供了一条捷径。
• Copper-catalyzed synthesis of 2-sulfenylindoles from indoline-2-thiones and aryl iodides
  作者：Shiping Zhou、Genhua Xiao、Yun Liang

  DOI：10.1016/j.tetlet.2016.12.028

  日期：2017.1

  A novel and efficient method for synthesis of 2-sulfenylindole via copper-catalyzed coupling reaction of indoline-2-thiones with aryl iodides has been developed. A series of N-substituted and N-free 2-sulfenylindole were obtained in high yields. Furthermore, the method was employed to synthesis of benzothieno[2,3-b]indoles from indoline-2-thiones with 1,2-diiodobenzene in the presence of CuI and Pd(OAc)2

  通过铜催化的吲哚-2-硫酮与芳基碘的偶联反应合成2-亚磺酰基吲哚的新方法已经得到了发展。以高收率获得了一系列的N-取代的和不含N的2-亚磺酰基吲哚。此外，该方法用于在CuI和Pd（OAc）2作为催化剂存在下，由吲哚啉-2-硫酮与1,2-二碘代苯合成苯并噻吩并[2,3- b ]吲哚。
• Acid-catalyzed isomerization of 3-indolyl sulfides to 2-indolyl sulfides: first synthesis of 3-unsubstituted 2-arylthioindoles. Evidence for a complex intermolecular process
  作者：Pierre Hamel、Yves Girard、Joseph G. Atkinson

  DOI：10.1021/jo00035a029

  日期：1992.4

  The acid-catalyzed isomerization of 3-indolyl sulfides 1 to the corresponding 2-indolyl sulfides 4 provides the first synthesis of 3-unsubstituted 2-(arylthio)indoles, a hitherto unattainable class of compounds. When catalyzed by trifluoroacetic acid, the isomerization proceeds mainly via an intermolecular mechanism involving initial disproportionation to a 2,3-indolyl bis-sulfide 5 and an unsubstituted counterpart 6 followed by further interaction of these species to yield the rearranged isomer 4. A mechanism is proposed involving a role for the acid in the sulfenyl-transfer steps. This type of process also occurs, to a lesser extent, in the polyphosphoric acid catalyzed isomerization.