1-allyl-1H-indole-5-carbonitrile | 1447159-92-3

• 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: 1-allyl-1H-indole-5-carbonitrile
• 英文别名: 1-Prop-2-enylindole-5-carbonitrile；1-prop-2-enylindole-5-carbonitrile
• CAS: 1447159-92-3
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: QAOMJLLXAYVYEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-allyl-1H-indole-5-carbonitrile 在 palladium diacetate 、 水 、 联硼酸频那醇酯 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以87%的产率得到1-propyl-1H-indole-5-carbonitrile
  参考文献：
  名称：

  从水中生成氢：在环境条件下使用Diboron试剂进行Pd催化的水还原

  摘要：

  从可再生资源，特别是从水生产氢是一个密集的研究领域，在氢经济中具有深远的意义。提出了一种均相催化方法，该方法是在环境反应条件下，在水与二硼化合物作为还原剂的反应中，由水生产干净的氢气。Pd催化体系在水中稳定，并具有出色的可回收性。羟基类似物（例如醇）与Pd / B 2 Pin 2系统兼容，可有效产生氢气。在钯存在下，B 2 Pin 2 -H 2 O系统是用于烯烃选择性加氢的出色催化系统。

  DOI：

  10.1021/acs.orglett.6b02508
• 作为产物：
  描述：

  5-氰基吲哚 、 3-溴丙烯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以94%的产率得到1-allyl-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Regioselective N-allylation and N-cinnamylation of indoles using CuI-exchanged hierarchical nanoporous material

  摘要：

  Regioselective N-allylation and N-cinnamylation of indoles are achieved using a novel catalyst of Cu-I-exchanged hierarchically architectured nanoporous material (MMZ(Cu)(Y)(I)). The catalyst was characterized by electron microscopy and X-ray methods. Other advantages like functional tolerance, easy separation and reusability of the catalyst are also highlighted. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2015.07.022

文献信息

• Pd-Boron-Catalyzed One Carbon Isomerization of Olefins: Water Assisted Process at Room Temperature
  作者：Devi Prasan Ojha、Karthik Gadde、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.joc.7b00580

  日期：2017.5.5

  ne-system -catalyzed isomerization of olefins has been uncovered. An efficient catalytic combination of [Pd(OAc)2]3-boronate-PCy3-enabled olefin isomerization at 80 °C has been investigated. Addition of water to the reaction showed a remarkable improvement and the isomerization occurred at ambient temperature. These catalytic systems function efficiently for the isomerization of functionalized as well

  现已发现钯-硼酸酯/硼烷体系催化的烯烃异构化。的有效的催化组合[将Pd（OAc）2 ] 3 -硼酸-PCY 3 -启用烯烃异构化在80℃下进行了研究。向反应中添加水显示出显着的改善，并且在环境温度下发生了异构化。这些催化体系有效地用于官能化的和未官能化的烯烃的异构化。催化条件显示了非氢化物和金属氢化物介质的参与，并且可以与水作为添加剂互换。
• Pd-mediated construction of a cyclopentane ring fused with indoles
  作者：Bagineni Prasad、B. Yogi Sreenivas、G. Rama Krishna、Ravikumar Kapavarapu、Manojit Pal

  DOI：10.1039/c3cc42309c

  日期：——

  Unprecedented synthesis of functionalized indoles of potential pharmacological interest has been developed via a Pd-mediated cascade reaction involving an intramolecular Heck coupling followed by the construction of a fused cyclopentane ring in a single pot.

  已开发出一种前所未有的功能化吲哚的合成方法，这种方法通过钯介导的级联反应实现，涉及到分子内Heck偶联反应，并在一个反应中构建了一个融合的环戊烷环，这些吲哚具有潜在的药理学兴趣。
• The Selective Nickel‐Catalyzed <i>N</i> ‐Allylation of C3‐Unprotected Indoles under Mild and Clean Conditions
  作者：Bouchaib Mouhsine、Abdallah Karim、Clément Dumont、Anthony Saint Pol、Isabelle Suisse、Mathieu Sauthier

  DOI：10.1002/ejoc.202200042

  日期：2022.7.14

  AbstractA simple salt free and selective N‐allylation of indoles with allylic alcohols has been developed. The protocol uses a catalytic amount of a nickel complex generated in situ from Ni(cod)2 and dppf as diphosphine. The use of DMSO as the reaction solvent is crucial to control the regioselectivity of the reaction with the exclusive formation of the N‐allyl product among up to three possible products.
• Generation of Hydrogen from Water: A Pd-Catalyzed Reduction of Water Using Diboron Reagent at Ambient Conditions
  作者：Devi Prasan Ojha、Karthik Gadde、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.orglett.6b02508

  日期：2016.10.7

  particularly from water, is an intensive area of research, which has far-reaching relevance in hydrogen economy. A homogeneous catalytic method is presented for producing clean hydrogen gas from water, in a reaction of water with a diboron compound as the reductant, under ambient reaction conditions. The Pd-catalytic system is stable in water and displays excellent recyclability. Hydroxy analogues

  从可再生资源，特别是从水生产氢是一个密集的研究领域，在氢经济中具有深远的意义。提出了一种均相催化方法，该方法是在环境反应条件下，在水与二硼化合物作为还原剂的反应中，由水生产干净的氢气。Pd催化体系在水中稳定，并具有出色的可回收性。羟基类似物（例如醇）与Pd / B 2 Pin 2系统兼容，可有效产生氢气。在钯存在下，B 2 Pin 2 -H 2 O系统是用于烯烃选择性加氢的出色催化系统。
• Regioselective N-allylation and N-cinnamylation of indoles using CuI-exchanged hierarchical nanoporous material
  作者：S. Senthilkumar、M. Kumarraja

  DOI：10.1016/j.catcom.2015.07.022

  日期：2015.10

  Regioselective N-allylation and N-cinnamylation of indoles are achieved using a novel catalyst of Cu-I-exchanged hierarchically architectured nanoporous material (MMZ(Cu)(Y)(I)). The catalyst was characterized by electron microscopy and X-ray methods. Other advantages like functional tolerance, easy separation and reusability of the catalyst are also highlighted. (C) 2015 Elsevier B.V. All rights reserved.