1-(4-chlorophenyl)-3-(1H-indol-3-yl)-3-p-tolylpropan-1-one | 1190763-70-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(4-chlorophenyl)-3-(1H-indol-3-yl)-3-p-tolylpropan-1-one
• 英文别名: 3-(3-indolyl)-1-(4-chlorophenyl)-3-(4-methylphenyl)propan-1-one；1-(4-chlorophenyl)-3-(1H-indol-3-yl)-3-(4-methylphenyl)propan-1-one
• CAS: 1190763-70-2
• 化学式: C₂₄H₂₀ClNO
• 分子量: 373.882
• InChiKey: ZVLTUDAHXKLOLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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 、 1-(4-chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one 在 [PyN(CH₂)4SO₃H][p-CH₃PhSO₃] 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以94%的产率得到1-(4-chlorophenyl)-3-(1H-indol-3-yl)-3-p-tolylpropan-1-one
  参考文献：
  名称：

  使用布朗斯台德酸离子液体作为有效催化剂，将吲哚与 α,β-不饱和酮共轭加成。

  摘要：

  布朗斯台德酸离子液体 [PyN(CH(2))(4)SO(3)H][p-CH(3)PhSO(3)] 已被报道为吲哚与 α 的迈克尔加成反应的有效催化剂,β-不饱和酮。获得了令人满意的结果，具有优异的产率和简单的实验程序。该催化剂最多可循环使用3次，催化活性没有任何明显下降。

  DOI：

  10.3390/molecules14093222

文献信息

• Alkylation of Indoles with α,β‐Unsaturated Ketones using Alumina in Hexanes
  作者：Xiong Zhang、Ebenezer Jones‐Mensah、Jackson Deobald、Jakob Magolan

  DOI：10.1002/adsc.201901037

  日期：2019.12.17

  We evaluated the influence of solvent on the alumina‐promoted C3‐alkylation of indoles with α,β‐unsaturated ketones. We found that lipophilic solvents were generally superior to hydrophilic ones with hexanes offering the 3‐alkyl indole products in high yields. Thus, we demonstrate an inexpensive and procedurally simple new process that pairs acidic alumina with hexanes to achieve this important Michael

  我们评估了溶剂对带有α，β-不饱和酮的吲哚的氧化铝促进的C3-烷基化的影响。我们发现亲脂性溶剂通常优于亲水性溶剂，而己烷可提供高收率的3-烷基吲哚产物。因此，我们证明了一种廉价且程序简单的新方法，该方法将酸性氧化铝与己烷配对以实现这一重要的迈克尔烷基化反应。底物范围包括二十四个实例，反应产率为61％至96％。
• Acidic Ionic Liquid–Catalyzed Highly Efficient Reaction of Indoles to α,β‐Unsaturated Ketones
  作者：Da‐gong Gu、Shun‐jun Ji、Hong‐xia Wang、Qiu‐yan Xu

  DOI：10.1080/00397910701866304

  日期：2008.3.28

  Abstract A novel method for the Michael reaction of indoles to α,β‐unsaturated ketones catalyzed by acidic ionic liquid is reported. We obtained the corresponding products in excellent yields in the presence of [hmim]HSO4. Development of this method has resulted in a new protocol for the synthesis of β‐indolylketones.

  摘要 报道了一种酸性离子液体催化吲哚与α,β-不饱和酮迈克尔反应的新方法。我们在 [hmim]HSO4 存在下以极好的收率获得了相应的产品。这种方法的发展导致了合成 β-吲哚基酮的新方案。
• Conjugate Addition of Indoles to α,β-Unsaturated Ketones Using a Brønsted Acid Ionic Liquid as an Efficient Catalyst
  作者：Chuan-Ji Yu、Chen-Jiang Liu

  DOI：10.3390/molecules14093222

  日期：——

  The Brønsted acid ionic liquid [PyN(CH(2))(4)SO(3)H][p-CH(3)PhSO(3)] has been reported as an efficient catalyst for the Michael addition reaction of indoles to alpha,beta-unsaturated ketones. Satisfactory results were obtained, with excellent yields and a simple experimental procedure. The catalyst could be recycled and reused up to three times without any noticeable decrease in the catalytic activity

  布朗斯台德酸离子液体 [PyN(CH(2))(4)SO(3)H][p-CH(3)PhSO(3)] 已被报道为吲哚与 α 的迈克尔加成反应的有效催化剂,β-不饱和酮。获得了令人满意的结果，具有优异的产率和简单的实验程序。该催化剂最多可循环使用3次，催化活性没有任何明显下降。
• Sulfonated carbon/silica composite functionalized Lewis acids for one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles, 3,4-dihydropyrimidin-2(1H)-ones and for Michael addition of indole to α,β-unsaturated ketones
  作者：Princy Gupta、Satya Paul

  DOI：10.1016/j.molcata.2011.10.016

  日期：2012.1

  Novel Lewis acid catalysts were prepared from sulfonated carbon/silica composites derived from starch and silica by treatment with Lewis acids AlCl3, SbCl3, Bi(NO3)(3), ZnCl2 and FeCl3. The catalytic activity of the Lewis acids was evaluated for one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles, 3,4-dihydropyrimidin-2(1H)-ones and for Michael addition of indole to alpha,beta-unsaturated ketones. Different Lewis acids were investigated with a view to select the most effective solid Lewis acid for organic synthesis. All the Lewis acid catalysts were characterized by FTIR, XRD and AAS analysis and the most active catalyst CSC-Star-SO3-AlCl2 was also characterized by TGA, SEM and TEM. (C) 2011 Elsevier B.V. All rights reserved.
• Ionic liquid coated sulfonated carbon/silica composites: novel heterogeneous catalysts for organic syntheses in water
  作者：Princy Gupta、Manmeet Kour、Satya Paul、James H. Clark

  DOI：10.1039/c3ra45229h

  日期：——

  Ionic liquid coated sulfonic acid functionalized amorphous carbon/silica composites derived from a starch–glucose mixture were developed and their catalytic activities were evaluated for Knoevenagel condensation, reductive amination of aldehydes and ketones, and for Michael addition of indole to α,β-unsaturated ketones in aqueous medium. The catalyst prepared from starch–glucose mixture (3 : 1) [CSC-Star-Glu-IL2]

  开发了一种由淀粉-葡萄糖混合物衍生的离子液体涂覆的磺酸官能化的无定形碳/二氧化硅复合材料，并对其催化活性进行了Knoevenagel缩合，醛和酮的还原胺化以及吲哚向α，β-不饱和酮的迈克尔加成反应的评估。在水性介质中。由淀粉-葡萄糖混合物（3：1）[CSC-Star-Glu-IL2]制备的催化剂在水中的活性最高。通过FTIR，TGA，元素分析对催化剂进行表征，并通过XRD，SEM和TEM对最具活性的催化剂进行表征。