(3-Methoxyphenyl)-(1-methylindol-3-yl)methanone | 1096979-13-3

• 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: (3-Methoxyphenyl)-(1-methylindol-3-yl)methanone
• CAS: 1096979-13-3
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: WSQBXNJDWXTKRY-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：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-Methoxyphenyl)-(1-methylindol-3-yl)methanone 在 氧气 、 palladium diacetate 、 potassium carbonate 、 三甲基乙酸 作用下， 反应 30.0h， 以74%的产率得到2-Methoxy-5-methylindeno[1,2-b]indol-10-one
  参考文献：
  名称：

  Intramolecular oxidative coupling of 3-indolylarylketones with Pd(II)-catalysis under air: convenient access to indenoindolones

  摘要：

  A Pd-catalyzed method has been developed for the intramolecular oxidative coupling of 3-indolylarylketones under open air as terminal oxidant toward the synthesis of indeno[1,2-b]indol-10(5H)-ones. This reaction represents an intramolecular coupling with dual activation of C-H bonds for electron-deficient arenes, while such reactions are common for electron-rich arenes. Pd(II)-catalysis with pivalic acid as co-catalyst has been found to be crucial. The reaction undergoes without indole N-H-protection. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.076
• 作为产物：
  描述：

  1-甲基吲哚 、 一氧化碳 、 3-甲氧基苯硼酸 在 吡啶 、 碘 、 palladium diacetate 、 cesium fluoride 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以68%的产率得到(3-Methoxyphenyl)-(1-methylindol-3-yl)methanone
  参考文献：
  名称：

  钯催化的吲哚羰基化合成吲哚-3-基芳基酮

  摘要：

  开发了一种新型的钯催化的吲哚羰基化反应，用CO和芳香族硼酸合成吲哚-3-基芳基酮。该反应可耐受各种官能团，并在温和条件下以高收率得到各种有价值的吲哚-3-基芳基酮。

  DOI：

  10.1021/cs5019106

文献信息

• Palladium-Catalyzed Carbonylation of Indoles for Synthesis of Indol-3-yl Aryl Ketones
  作者：Mi-Na Zhao、Longfei Ran、Ming Chen、Zhi-Hui Ren、Yao-Yu Wang、Zheng-Hui Guan

  DOI：10.1021/cs5019106

  日期：2015.2.6

  A novel palladium-catalyzed carbonylation of indoles with CO and aromatic boronic acids for the synthesis of indol-3-yl aryl ketones was developed. The reaction tolerates a wide range of functional groups and gives a variety of valuable indol-3-yl aryl ketones in high yields under mild conditions.

  开发了一种新型的钯催化的吲哚羰基化反应，用CO和芳香族硼酸合成吲哚-3-基芳基酮。该反应可耐受各种官能团，并在温和条件下以高收率得到各种有价值的吲哚-3-基芳基酮。
• Intramolecular oxidative coupling of 3-indolylarylketones with Pd(II)-catalysis under air: convenient access to indenoindolones
  作者：Sankar K. Guchhait、Maneesh Kashyap、Somnath Kandekar

  DOI：10.1016/j.tetlet.2012.05.076

  日期：2012.7

  A Pd-catalyzed method has been developed for the intramolecular oxidative coupling of 3-indolylarylketones under open air as terminal oxidant toward the synthesis of indeno[1,2-b]indol-10(5H)-ones. This reaction represents an intramolecular coupling with dual activation of C-H bonds for electron-deficient arenes, while such reactions are common for electron-rich arenes. Pd(II)-catalysis with pivalic acid as co-catalyst has been found to be crucial. The reaction undergoes without indole N-H-protection. (C) 2012 Elsevier Ltd. All rights reserved.