4-(1H-indol-3-yl)nonan-2-one

• 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)nonan-2-one
• 英文别名: 4-(1H-3-indolyl)-2-nonanone
• 化学式: C₁₇H₂₃NO
• 分子量: 257.376
• InChiKey: DUPXOCWHSWEYIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吲哚 、 3-壬烯-2-酮 在 tin(II) chloride dihdyrate 作用下， 以 异丙醇 为溶剂， 反应 96.0h， 以96%的产率得到4-(1H-indol-3-yl)nonan-2-one
  参考文献：
  名称：

  金属卤化物水合物作为路易斯酸催化剂，用于吲哚和活性烯烃的共轭弗里德工艺反应

  摘要：

  研究了金属卤化物水合物如SnCl2·2H2O，MnCl2·4H2O，SrCl2·6H2O，CrCl2·6H2O，CoCl2·6H2O和CeCl3·7H2O作为温和的路易斯酸催化剂，用于吲哚和活性烯烃之间的共轭Friedel-Crafts反应。反应在室温下用脂族不饱和酮在几天内进行，而查耳酮仅在回流条件下反应。与硝基苯乙烯的反应在溶剂中或在无溶剂条件下进行。在所有情况下，均获得了合理至良好的产量。

  DOI：

  10.1590/s0103-50532011000400003

文献信息

• Metal halide hydrates as lewis acid catalysts for the conjugated friedel-crafts reactions of indoles and activated olefins
  作者：Cristiane S. Schwalm、Marco Antonio Ceschi、Dennis Russowsky

  DOI：10.1590/s0103-50532011000400003

  日期：——

  CrCl2·6H2O, CoCl2·6H2O e CeCl3·7H2O were investigated as mild Lewis acids catalysts for the conjugate Friedel-Crafts reaction between indoles and activated olefins. The reactions were carried out with aliphatic unsaturated ketones over a period of days at room temperature, while chalcones reacted only under reflux conditions. The reactions with nitrostyrenes were either performed in solvent or under

  研究了金属卤化物水合物如SnCl2·2H2O，MnCl2·4H2O，SrCl2·6H2O，CrCl2·6H2O，CoCl2·6H2O和CeCl3·7H2O作为温和的路易斯酸催化剂，用于吲哚和活性烯烃之间的共轭Friedel-Crafts反应。反应在室温下用脂族不饱和酮在几天内进行，而查耳酮仅在回流条件下反应。与硝基苯乙烯的反应在溶剂中或在无溶剂条件下进行。在所有情况下，均获得了合理至良好的产量。
• The Michael Addition of Indoles to α,β-Unsaturated Ketones Catalyzed by CeCl₃·7H₂O−NaI Combination Supported on Silica Gel¹
  作者：Giuseppe Bartoli、Massimo Bartolacci、Marcella Bosco、Gioia Foglia、Arianna Giuliani、Enrico Marcantoni、Letizia Sambri、Elisabetta Torregiani

  DOI：10.1021/jo034303y

  日期：2003.5.1

  Alkylation of indoles by means of the Michael addition has been the subject of a number of investigation. It is well established that regioselectivity in the additions of indoles to electron-deficient alkenes is strongly controlled by the reaction medium. In a continuation of the work on developing greener and cleaner technologies, the cerium(III) chloride heptahydrate and sodium iodide combination

  通过迈克尔加成反应使吲哚烷基化已成为许多研究的主题。众所周知，反应介质强烈地控制了吲哚向缺电子烯烃的加成中的区域选择性。在继续开发更环保，更清洁技术的工作中，负载在硅胶上的七水合氯化铈（III）和碘化钠的组合催化各种吲哚与α，β-不饱和酮的烷基化，生成3-（3-氧代烷基）吲哚衍生品收益率高。吲哚核上的取代仅发生在3位，并且未观察到N-烷基化产物。
• Synthesis and Structures of Air-Stable Binuclear Hafnocene Perfluorobutanesulfonate and Perfluorobenzenesulfonate and their Catalytic Application in CC Bond-Forming Reactions
  作者：Ningbo Li、Xiaohong Zhang、Xinhua Xu、Yun Chen、Renhua Qiu、Jinyang Chen、Xie Wang、Shuang-Feng Yin

  DOI：10.1002/adsc.201300439

  日期：2013.8.12

  AbstractThe two air‐stable μ2‐hydroxy‐bridged binuclear hafnocene perfluorobutanesulfonate and perfluorobenzenesulfonate complexes were successfully synthesized. The high catalytic activity and recyclability of these complexes were exemplified for various carbon‐carbon bond formation reactions. Compared with our previously reported hafnocene perfluorooctanesulfonate, these complexes show stronger Lewis acidity and better catalytic activity, and should find broad applications in organic synthesis.magnified image
• Strong Lewis acids of air-stable binuclear triphenylantimony(V) complexes and their catalytic application in C–C bond-forming reactions
  作者：Ningbo Li、Renhua Qiu、Xiaohong Zhang、Yun Chen、Shuang-Feng Yin、Xinhua Xu

  DOI：10.1016/j.tet.2015.05.013

  日期：2015.6

  Two air-stable novel Lewis acids of triphenylantimony(V) pentafluorbezenesulfonates (2) and perfluorooctanesulfonates (3) were successfully synthesized and characterized. X-ray studies and thermo-gravimetric analysis found that these complexes showed high anti-hydrolyzability and thermal stability. The high catalytic activity and excellent recyclability of these complexes were achieved in the Michael

  成功地合成和表征了两种空气稳定的新颖的三苯基锑（V）五氟苯磺酸磺酸盐（2）和全氟辛烷磺酸盐（3）的路易斯酸。X射线研究和热重分析发现，这些配合物显示出很高的抗水解性和热稳定性。在迈克尔加成反应和烯丙基化反应中实现了这些配合物的高催化活性和优异的可回收性。由于它们的稳定性，可存储性以及催化效率，这些配合物在有机合成中应具有广泛的用途。