N-Methyl-2-(4-phenylcyclohexen-1-yl)indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-Methyl-2-(4-phenylcyclohexen-1-yl)indole
• 英文别名: 1-Methyl-2-(4-phenylcyclohexen-1-yl)indole
• 化学式: C₂₁H₂₁N
• 分子量: 287.404
• InChiKey: AFGHZGQVMKGQHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  4-phenylcyclohex-1-enyl trifluoromethanesulfonate 、 N -甲基- 2 -(三正丁基锡)吲哚 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以90%的产率得到N-Methyl-2-(4-phenylcyclohexen-1-yl)indole
  参考文献：
  名称：

  Indol-2-yltributylstannane: A Versatile Reagent for 2-Substituted Indoles

  摘要：

  A general method for 2-substituted indoles via the palladium-catalyzed coupling of indol-2-ylstannanes is described. (N-Methylindol-2-yl)tributylstannane (1) reacts with a variety of electrophiles under very mild conditions: [N-tert-Butoxycarbonyl)indol-2-yl]tributylstannane (3) is much less reactive in the coupling reactions and reacts only with certain activated electrophiles. [N-[[(Trimethylsilyl)ethoxy]methylindol-2-yl]tributylstannane (4) behaves similarly to 1 and the removal of the [(trimethylsilyl)ethoxy]methyl group can be achieved with tetra-n-butylammonium fluoride in DMF in the presence of ethylenediamine.

  DOI：

  10.1021/jo00094a042

文献信息

• Synergistic silver-mediated and palladium-catalyzed nondirected olefination of aryl C–H bond: quick access to multi-substituted aryl olefins
  作者：Jian Yao、Lili Shao、Xiaohong Huo、Xiaoming Wang

  DOI：10.1007/s11426-023-1834-2

  日期：2024.3

  Abstract Transition metal-catalyzed olefination of aryl C–H bond is a powerful tool for the synthesis of alkenes. While the Pd-catalyzed oxidative C–H olefination of arenes, also known as Fujiwara-Moritani reaction, has been established as one of the most efficient methods, the substrates are largely limited to terminal olefins with electron-withdrawing group(s). Herein, we report a synergistic silver-mediated

  摘要 过渡金属催化的芳基C-H键烯化是合成烯烃的有力工具。虽然 Pd 催化的芳烃氧化 C-H 烯化反应（也称为 Fujiwara-Moritani 反应）已被确定为最有效的方法之一，但底物很大程度上限于具有吸电子基团的末端烯烃。在此，我们报道了银介导和钯催化的芳烃与乙烯基（拟）卤化物的协同非定向C-H烯化反应，这为典型的Fujiwara-Moritani反应提供了补充策略。各种卤代芳烃、杂芳烃和烯烃底物的反应均进展顺利，为各种多取代芳基烯烃提供了有效的途径，包括三取代/四取代烯烃和源自药物或天然产物的几种复杂烯烃。机理研究表明双金属 Pd/Ag 合作在催化中有效，即反应是通过与膦/Ag 物质连接而导致芳基 C-H 键断裂引发的，然后将芳基部分转移到乙烯基钯中间体上，从而生成乙烯基钯中间体。进而通过将乙烯基（拟）卤化物氧化加成到钯络合物上而形成。该方法能够以简化且可控的方式从简单的芳烃（无导
• Labadie Sharada S., Teng Edmond, J. Org. Chem, 59 (1994) N 15, S 4250-4254
  作者：Labadie Sharada S., Teng Edmond

  DOI：——

  日期：——
• Indol-2-yltributylstannane: A Versatile Reagent for 2-Substituted Indoles
  作者：Sharada S. Labadie、Edmond Teng

  DOI：10.1021/jo00094a042

  日期：1994.7

  A general method for 2-substituted indoles via the palladium-catalyzed coupling of indol-2-ylstannanes is described. (N-Methylindol-2-yl)tributylstannane (1) reacts with a variety of electrophiles under very mild conditions: [N-tert-Butoxycarbonyl)indol-2-yl]tributylstannane (3) is much less reactive in the coupling reactions and reacts only with certain activated electrophiles. [N-[[(Trimethylsilyl)ethoxy]methylindol-2-yl]tributylstannane (4) behaves similarly to 1 and the removal of the [(trimethylsilyl)ethoxy]methyl group can be achieved with tetra-n-butylammonium fluoride in DMF in the presence of ethylenediamine.