3-benzoyl-1H-indole-5-carbonitrile | 17380-22-2

• 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-benzoyl-1H-indole-5-carbonitrile
• 英文别名: Indole-5-carbonitrile, 3-benzoyl-
• CAS: 17380-22-2
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: VDSVHHGVSMIFOY-UHFFFAOYSA-N

物化性质

• 沸点：
  493.5±25.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氰基吲哚 、 苯乙酸乙酯 在 potassium tert-butylate 、 copper diacetate 、 二甲基亚砜 作用下， 反应 24.0h， 以81%的产率得到3-benzoyl-1H-indole-5-carbonitrile
  参考文献：
  名称：

  通过铜介导的芳基乙酸乙酯的氧化脱碳乙氧基化合成3-acylindoles。

  摘要：

  通过在DMSO中使用Cu（OAc）2和KOtBu对易得的芳基乙酸乙酯进行氧化脱碳乙氧基化，已经实现了游离吲哚（NH）的有效区域选择性C-3酰化。

  DOI：

  10.1039/c9ob02550b

文献信息

• Decarboxylative/decarbonylative C3-acylation of indoles via photocatalysis: a simple and efficient route to 3-acylindoles
  作者：Qing Shi、Pinhua Li、Xianjin Zhu、Lei Wang

  DOI：10.1039/c6gc00516k

  日期：——

  A simple and efficient strategy for the preparation of 3-acylindoles via visible-light promoted C3-acylation of free (NH)- and N-substituted indoles with a-oxocarboxylic acids was developed. The reaction tolerates a wide...

  开发了一种简单有效的策略，通过可见光促进游离（NH）-和N-取代的吲哚与α-氧代羧酸的C3-酰化反应来制备3-酰基。该反应可耐受多种...
• Regioselective Friedel–Crafts Acylation of Indoles Catalysed by Zinc Oxide in an Ionic Liquid
  作者：Li-Rong Zhang、Feng-Ping Yi、Jian-Zhong Zou、Xuan Zhang、Zhen Wang

  DOI：10.3184/174751912x13460004925054

  日期：2012.10

  A facile method for the regioselective Friedel–Crafts acylation of indoles with acyl chlorides catalysed by zinc oxide in an ionic liquid medium has been developed. The corresponding 3-acylindoles were obtained in good to high yields under mild reaction conditions. Zinc oxide, which is easily available and requires no special handling procedures, is an efficient catalyst for acylation of indoles.

  本研究开发了一种在离子液体介质中以氧化锌为催化剂，对吲哚与酰基氯进行区域选择性弗里德尔-卡夫酰化反应的简便方法。在温和的反应条件下，获得了相应的 3-酰基吲哚，收率从好到高。氧化锌易于获得，无需特殊处理程序，是吲哚酰化反应的高效催化剂。
• Boron Trifluoride Etherate Promoted Regioselective 3-Acylation of Indoles with Anhydrides
  作者：Yunyun Zheng、Jiuling Li、Kai Wei

  DOI：10.3390/molecules27238281

  日期：——

  An efficient, high-yielding and scalable procedure for the regioselective 3-acylation of indoles with anhydrides promoted by boron trifluoride etherate under mild conditions was reported. This novel protocol provided a simple way to prepare 3-(benzofuran-2-yl) indole in three steps.

  报道了一种高效、高产且可扩展的程序，用于在温和条件下通过乙醚三氟化硼促进吲哚与酸酐的区域选择性 3-酰化。这种新颖的方案提供了一种分三步制备 3-(benzofuran-2-yl) 吲哚的简单方法。
• Mild and Selective Ru-Catalyzed Formylation and Fe-Catalyzed Acylation of Free (N–H) Indoles Using Anilines as the Carbonyl Source
  作者：Wenliang Wu、Weiping Su

  DOI：10.1021/ja2048495

  日期：2011.8.10

  C3-selective formylation and acylation of free (N-H) indoles under mild conditions can be achieved by using Ru- and Fe-catalyzed oxidative coupling of free (N-H) indoles with anilines, respectively. Both processes are operationally simple, compatible with a variety of functional groups and generally provide the desired products in good yields. (13)C-labeling experiments unambiguously established that the carbonylic carbon in the formylation products originated from methyl group of N-methyl aniline.
• Synthesis of 3-acylindoles <i>via</i> copper-mediated oxidative decarbethoxylation of ethyl arylacetates
  作者：Anjali Jaiswal、Anup Kumar Sharma、Krishna Nand Singh

  DOI：10.1039/c9ob02550b

  日期：——

  An efficient regioselective C-3 acylation of free indoles (N-H) has been accomplished via oxidative decarbethoxylation of easily available ethyl arylacetates using Cu(OAc)2 and KOtBu in DMSO.

  通过在DMSO中使用Cu（OAc）2和KOtBu对易得的芳基乙酸乙酯进行氧化脱碳乙氧基化，已经实现了游离吲哚（NH）的有效区域选择性C-3酰化。