(2-chlorophenyl)(1-methyl-1H-indol-3-yl)methanone | 1094749-50-4

• 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: (2-chlorophenyl)(1-methyl-1H-indol-3-yl)methanone
• 英文别名: (2-Chlorophenyl)-(1-methylindol-3-yl)methanone
• CAS: 1094749-50-4
• 化学式: C₁₆H₁₂ClNO
• mdl: MFCD12653890
• 分子量: 269.73
• InChiKey: BXUARHYRLVXLKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  邻氯苯乙酮 在 吡啶 、 selenium(IV) oxide 、 copper(II) acetate monohydrate 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 (2-chlorophenyl)(1-methyl-1H-indol-3-yl)methanone
  参考文献：
  名称：

  Copper-promoted decarboxylative direct C3-acylation of N-substituted indoles with α-oxocarboxylic acids

  摘要：

  开发了一种新型高效的铜促进脱羧直接C3酰基化反应，以α-氧代羧酸作为酰基源，用于N-取代吲哚合成3-酰基吲哚。

  DOI：

  10.1039/c3cc40389k

文献信息

• Palladium-Catalyzed Carbonylation of Indoles using Aryl Formates as Bifunctional Reagents: A Route to Indol-3-yl Aryl Ketones
  作者：Li-Jun Gu、Yu-Shen Wang、Hong-Tao Zhang、Huai-Jun Tang、Gan-Peng Li、Ming-Long Yuan

  DOI：10.1002/cctc.201600433

  日期：2016.7.6

  A new Pd‐catalyzed carbonylation of indoles for the synthesis of indol‐3‐yl aryl ketones under CO‐free conditions was developed. The reaction showed a broad substrate scope with moderate to excellent yields.

  开发了一种新的钯催化的吲哚羰基化反应，用于在无CO条件下合成吲哚-3-基芳基酮。反应显示出广泛的底物范围，具有中等至优异的产率。
• Facile Access to 3-Acylindoles through Palladium-Catalyzed Addition of Indoles to Nitriles: The One-Pot Synthesis of Indenoindolones
  作者：Yuanhong Ma、Jingsong You、Feijie Song

  DOI：10.1002/chem.201203354

  日期：2013.1.21

  The palladium‐catalyzed addition of indoles to nitriles affords 3‐acylindoles. The reaction proceeds with high selectivity, wide substrate scope, broadly available starting materials, and an operationally simple procedure. Combination with the palladium‐catalyzed intramolecular oxidative coupling of 3‐indolylarylketone gives access to indenoindolones in a one‐pot synthesis.

  关联性良好：钯催化的吲哚在腈中的加成反应生成3-acylindoldols。反应以高选择性，广泛的底物范围，广泛可用的起始原料和操作简单的方法进行。与钯催化的3-吲哚基芳基酮的分子内氧化偶合相结合，可在一锅合成中获得茚并吲哚酮。
• Acylation of indoles via photoredox catalysis: a route to 3-acylindoles
  作者：Lijun Gu、Cheng Jin、Jiyan Liu、Hongtao Zhang、Minglong Yuan、Ganpeng Li

  DOI：10.1039/c5gc01931a

  日期：——

  A visible-light-catalyzed synthesis of 3-acylindoles from simple indoles and α-oxo acids at room temperature has been discovered. This method offers rapid access to 3-acylindoles through C–C and C–H bond activation.

  一种在室温下通过可见光催化合成3-酰基吲哚的方法已被发现。该方法通过C-C和C-H键活化快速获得3-酰基吲哚。
• Visible light-induced carbonylation of indoles with arylsulfonyl chlorides and CO
  作者：Xiangguang Li、Deqiang Liang、Wenzhong Huang、Hongfu Zhou、Zhao Li、Baoling Wang、Yinhai Ma、Hai Wang

  DOI：10.1016/j.tet.2016.11.009

  日期：2016.12

  A novel and simple strategy for the visible light-induced efficient synthesis of indol-3-yl aryl ketones from readily available arylsulfonyl chlorides and indoles with CO at room temperature was developed. This metal-free protocol has good functional group tolerance and avoids the use of transition-metal catalysts, additives, and alkaline or acidic reaction medium.

  开发了一种新颖，简单的策略，用于在室温下用CO从可见的芳基磺酰氯和吲哚以可见光诱导的吲哚-3-基芳基酮的有效合成。这种不含金属的方案具有良好的官能团耐受性，并且避免使用过渡金属催化剂，添加剂以及碱性或酸性反应介质。
• 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。