4-((1H-indol-3-yl)methyl)benzonitrile | 1293391-63-5

• 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: 4-((1H-indol-3-yl)methyl)benzonitrile
• 英文别名: 4-(1H-indol-3-ylmethyl)benzonitrile
• CAS: 1293391-63-5
• 化学式: C₁₆H₁₂N₂
• 分子量: 232.285
• InChiKey: CMPZSKOTQNALKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-(hydroxy(1H-indol-3-yl)methyl)benzonitrile 在 二氢吡啶 、 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 8.0h， 以90%的产率得到4-((1H-indol-3-yl)methyl)benzonitrile
  参考文献：
  名称：

  通过无金属转移氢化制取C-3烷基取代的吲哚的高效途径

  摘要：

  开发了通过3-吲哚甲醇的完全无金属催化转移加氢制取C-3烷基取代的吲哚的高效途径。该过程是通过在布朗斯台德酸的存在下原位形成的乙烯基亚胺基中间体进行的，汉茨酯用作还原剂。在较大的基材范围内，还原效果非常好，几乎在所有情况下，成品率均超过90％。

  DOI：

  10.1016/j.tetlet.2014.05.064

文献信息

• Iron-Catalyzed Direct C3-Benzylation of Indoles with Benzyl Alcohols through Borrowing Hydrogen
  作者：Giovanni Di Gregorio、Michele Mari、Francesca Bartoccini、Giovanni Piersanti

  DOI：10.1021/acs.joc.7b01603

  日期：2017.8.18

  We present the coupling of primary and secondary benzyl alcohols with indoles to form 3-benzylated indoles and H2O that is catalyzed, for the first time, by a complex of earth-abundant iron. This transformation accommodates a variety of substrates and is distinguished by its operational simplicity, sustainability, high functional-group tolerance, and amenability to gram-scale synthesis. On the basis

  我们提出伯和仲苄醇与吲哚的偶合，以形成3-苄基化的吲哚和H 2 O，这是第一次由富地球的铁的复合物催化。这种转变可容纳多种底物，并且以其操作简单，可持续性，高官能团耐受性和对克级合成的适应性而著称。根据初步的实验观察，我们建议反应通过借入氢过程进行。
• 10.3390/molecules29092156
  作者：Guo, Guozhe、Zhang, Yuquan、Li, Yanchun、Li, Zhijun

  DOI：10.3390/molecules29092156

  日期：——

  The photoredox-catalyzed decarboxylative cross-coupling reaction of aryl acetic acids and aryl nitriles has been achieved under an argon atmosphere in high yields. This method provides a fast way to obtain prevalent aryl acetic acids from an abundant natural source. A tentative radical mechanism has been proposed.

  芳基乙酸和芳基腈的光氧化还原催化脱羧交叉偶联反应在氩气氛下以高产率实现。该方法提供了一种从丰富的天然来源中获取普遍的芳基乙酸的快速方法。已经提出了一种初步的激进机制。
• An efficient one-pot synthesis of 2-benzylpyrroles and 3-benzylindoles
  作者：Ratnesh Sharma、Mangilal Chouhan、Divya Sood、Vipin A. Nair

  DOI：10.1002/aoc.1759

  日期：2011.4

  AbstractOne‐pot regioselective benzylation of pyrroles and indoles using zirconium tetrachloride is discussed. This has been achieved by in‐situ generation of di(1H‐pyrrol‐1‐yl)zirconium(IV) chloride and di(1H‐indol‐1‐yl)zirconium(IV) chloride. It was observed that benzylation reactions of these complexes using n‐BuLi occurred at C‐2 position for pyrrole and C‐3 for indole. Copyright © 2011 John Wiley & Sons, Ltd.
• Involving Single-Atom Silver(0) in Selective Dehalogenation by AgF under Visible-Light Irradiation
  作者：Wenli Wu、Enxin Cui、Yun Zhang、Chen Zhang、Feng Zhu、Chen-Ho Tung、Yifeng Wang

  DOI：10.1021/acscatal.9b01929

  日期：2019.7.5

  The dehalogenation-arylation and the hydro-dehalogenation of various types of organic halides are selectively realized using AgF and visible light without any organic additives under mild conditions. Single-atom silver(0) (denoted as SAAg) serves as the catalytically active center, and the TOF of SAAg reaches 6000 h(-1). This elusive activity of Ag is beyond that expected from its ionic, nano, or bulk forms.
• A highly efficient route to C-3 alkyl-substituted indoles via a metal-free transfer hydrogenation
  作者：Cai Chen、Huan-Xi Feng、Zhi-Long Li、Pin-Wen Cai、Yan-Kai Liu、Lian-Hai Shan、Xian-Li Zhou

  DOI：10.1016/j.tetlet.2014.05.064

  日期：2014.7

  A highly efficient route to C-3 alkyl-substituted indoles via completely metal-free catalytic transfer hydrogenation of 3-indolemethanols was developed. This process proceeds via vinylogous iminium intermediates formed in situ in the presence of Brønsted acids, and Hantzsch ester is used as the reductant. The reduction works extremely well with a large substrate scope, and the yields exceed 90% in

  开发了通过3-吲哚甲醇的完全无金属催化转移加氢制取C-3烷基取代的吲哚的高效途径。该过程是通过在布朗斯台德酸的存在下原位形成的乙烯基亚胺基中间体进行的，汉茨酯用作还原剂。在较大的基材范围内，还原效果非常好，几乎在所有情况下，成品率均超过90％。