N-[4-bromo-2-(phenylethynyl)phenyl]methanesulfonamide | 442155-78-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4-bromo-2-(phenylethynyl)phenyl]methanesulfonamide
• 英文别名: N-[4-bromo-2-(2-phenylethynyl)phenyl]methanesulfonamide
• CAS: 442155-78-4
• 化学式: C₁₅H₁₂BrNO₂S
• 分子量: 350.236
• InChiKey: KYEGGZOPFWONIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[4-bromo-2-(phenylethynyl)phenyl]methanesulfonamide 在 copper dichloride 作用下， 以 苯甲腈 为溶剂， 反应 1.5h， 以96%的产率得到5-bromo-3-chloro-1-methylsulfonyl-2-phenylindole
  参考文献：
  名称：

  Simultaneous Functionalization and Cyclization of 2-Ethynylaniline Derivatives to Indoles

  摘要：

  Two different kind of sequential cyclization-functionalization are developed. Namely, cyclization-chlorination of 2-ethynylaniline derivatives using CuCl2 gave 3-chloro- and 3,5-dichloroindole derivatives. The plausible mechanism for this reaction is also discussed. On the other hand, the reaction between 2-ethynylaniline derivatives and Cu(NO3)(2)center dot 3H(2)O in THF provided C4-nitro compound. After being changed the solvent from THF to DMF, followed by heating, 5-nitroindole derivatives was afforded.

  DOI：

  10.3987/com-16-s(s)60
• 作为产物：
  描述：

  4 -溴- 2 - 碘苯甲胺 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 73.0h， 生成 N-[4-bromo-2-(phenylethynyl)phenyl]methanesulfonamide
  参考文献：
  名称：

  Cu（II）盐催化2-乙炔基苯胺衍生物合成吲哚环的有效方法的开发及其在天然产物合成中的应用

  摘要：

  研究了Cu（II）盐催化吲哚合成的有效方法的开发及其应用。已经证明，Cu（OAc）2是合成各种1-对甲苯磺酰基或1-甲基磺酰吲哚的最佳催化剂，这些1-对甲苯磺酰基或1-甲基磺酰吲哚在吲哚的芳环和C2位置均具有吸电子和供电子基团。对于初级苯胺衍生物，Cu（OCOCF 3）2表现出良好的活性，而Cu（OAc）2是仲苯胺环化的良好催化剂。该方法可用于在同一分子中具有亲电子部分的化合物的顺序环化反应。通过用KH预先处理，实现了顺序环化以提供三环系统，但第二个环化仅限于五元和六元环。最后，完成了以Cu（II）促进的吲哚合成为关键步骤的马匹的正式和全合成。

  DOI：

  10.1021/jo035528b

文献信息

• Efficient construction of indole rings from 2-ethynylaniline derivatives catalyzed by copper(II) salts and its application to the tandem cyclization reactions
  作者：Kou Hiroya、Shin Itoh、Mika Ozawa、Yuichi Kanamori、Takao Sakamoto

  DOI：10.1016/s0040-4039(01)02396-6

  日期：2002.2

  The efficient cyclization reactions of the N-methanesulfonyl or N-ethoxycarbonyl derivatives of 2-ethynylanilines, functionalized on the benzene ring and/or the acetylene terminal into indoles catalyzed by either Cu(OTf)2 or Cu(OAc)2 are accomplished. The application of this reaction to the tandem cyclization reaction is also described.

  通过Cu（OTf）2或Cu（OAc）2催化在苯环和/或乙炔末端官能化的2-乙炔基苯胺的N-甲磺酰基或N-乙氧基羰基衍生物的有效环化反应得以完成。还描述了该反应在串联环化反应中的应用。
• Mild and efficient cyclization reaction of 2-ethynylaniline derivatives to indoles in aqueous medium
  作者：Kou Hiroya、Shin Itoh、Takao Sakamoto

  DOI：10.1016/j.tet.2005.08.098

  日期：2005.11

  Results of the optimized cyclization reaction of 2-ethynyl aniline derivatives to indoles catalyzed by copper(II) salts are described. The reactions can be carried out in a mixture of H2O and MeOH in the presence of 1-ethylpiperidine at room temperature. These conditions can be applied to a bulky substrate, which is difficult to be cyclized efficiently by existing reaction conditions. Furthermore, this reaction condition was applied to a catalyst recycling reaction system. (c) 2005 Elsevier Ltd. All rights reserved.
• Development of an Efficient Procedure for Indole Ring Synthesis from 2-Ethynylaniline Derivatives Catalyzed by Cu(II) Salts and Its Application to Natural Product Synthesis
  作者：Kou Hiroya、Shin Itoh、Takao Sakamoto

  DOI：10.1021/jo035528b

  日期：2004.2.1

  The development of efficient methods for the indole synthesis catalyzed by Cu(II) salts and its applications were investigated. Cu(OAc)2 has been proved to be the best catalyst for the synthesis of various 1-p-tolylsulfonyl or 1-methylsulfonylindoles, which have both electron-withdrawing and electron-donating groups on the aromatic ring and C2 position of indoles. For the primary aniline derivatives

  研究了Cu（II）盐催化吲哚合成的有效方法的开发及其应用。已经证明，Cu（OAc）2是合成各种1-对甲苯磺酰基或1-甲基磺酰吲哚的最佳催化剂，这些1-对甲苯磺酰基或1-甲基磺酰吲哚在吲哚的芳环和C2位置均具有吸电子和供电子基团。对于初级苯胺衍生物，Cu（OCOCF 3）2表现出良好的活性，而Cu（OAc）2是仲苯胺环化的良好催化剂。该方法可用于在同一分子中具有亲电子部分的化合物的顺序环化反应。通过用KH预先处理，实现了顺序环化以提供三环系统，但第二个环化仅限于五元和六元环。最后，完成了以Cu（II）促进的吲哚合成为关键步骤的马匹的正式和全合成。
• Simultaneous Functionalization and Cyclization of 2-Ethynylaniline Derivatives to Indoles
  作者：Kou Hiroya、Shin Itoh、Kiyofumi Inamoto、Hiroki Shigehisa、Takao Sakamoto

  DOI：10.3987/com-16-s(s)60

  日期：——

  Two different kind of sequential cyclization-functionalization are developed. Namely, cyclization-chlorination of 2-ethynylaniline derivatives using CuCl2 gave 3-chloro- and 3,5-dichloroindole derivatives. The plausible mechanism for this reaction is also discussed. On the other hand, the reaction between 2-ethynylaniline derivatives and Cu(NO3)(2)center dot 3H(2)O in THF provided C4-nitro compound. After being changed the solvent from THF to DMF, followed by heating, 5-nitroindole derivatives was afforded.