3-(3-(4-methylphenyl)-3-oxopropyl)indole | 70447-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-(4-methylphenyl)-3-oxopropyl)indole
• 英文别名: 3-indol-3-yl-1-p-tolyl-propan-1-one；3-(1H-indol-3-yl)-1-(4-methylphenyl)propan-1-one
• CAS: 70447-30-2
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: GGDCTRSZIQDZEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-(3-(4-methylphenyl)-3-oxopropyl)indole 在 四丁基硫酸氢铵 、 一水合肼 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 二氯甲烷 、 乙二醇 为溶剂， 反应 0.25h， 生成 1-(3-(3-(p-tolyl)propyl)-1H-indol-1-yl)ethanone
  参考文献：
  名称：

  通过FeCl 3介导的含芳基或烯烃的3-取代的N-Ac吲哚环化反应合成3,3-螺二氢吲哚

  摘要：

  我们报道了通过取代的芳基的弗瑞德-克来福特反应或附加的烯烃的正式[2 + 2]环加成反应，可直接合成3,3-螺二氢吲哚的3取代的N-乙酰吲哚的环化反应。我们的策略涉及在FeCl 3介导的氢化反应或环化反应中吲哚核的C2═C3键的结合。

  DOI：

  10.1021/acs.orglett.6b00174
• 作为产物：
  描述：

  β-p-Toluyl-α-(3-indolyl)propionic-acid 以60%的产率得到
  参考文献：
  名称：

  GRIGORYAN G. V.; AGBALYAN S. G., XIMIYA GETEROTSIKL. SOEDIN., 1979, HO 3, 348-351

  摘要：

  DOI：

文献信息

• In situ generation of Iron(<scp>iii</scp>) dodecyl sulfate as Lewis acid-surfactant catalyst for synthesis of bis-indolyl, tris-indolyl, Di(bis-indolyl), Tri(bis-indolyl), tetra(bis-indolyl)methanes and 3-alkylated indole compounds in water
  作者：Hojat Veisi、Behrooz Maleki、Fereshteh Hosseini Eshbala、Hamed Veisi、Ramin Masti、Samaneh Sedigh Ashrafi、Mehdi Baghayeri

  DOI：10.1039/c4ra03194f

  日期：——

  Iron(III) dodecyl sulfate as Lewis acid-surfactant catalyst was prepared in situ and effectively used in the synthesis of bis(indolyl)methanes and Michael reactions of indoles with α,β-unsaturated carbonyl compounds in water. Also, this method was used for the synthesis of 1,1,3-tri-indolyl compounds, producing good to excellent yield at room temperature.

  采用原位法制备了路易斯酸-表面活性剂催化剂十二烷基硫酸铁(III)，并有效地用于水中双(吲哚基)甲烷的合成以及吲哚与α，β-不饱和羰基化合物的迈克尔加成反应。此外，该方法还可用于合成1,1,3-三吲哚化合物，在室温下获得良好至优异的产率。
• Cu-catalyzed β-functionalization of saturated ketones with indoles: a one-step synthesis of C3-substituted indoles
  作者：Zhao Yang、Chengkou Liu、Yu Zeng、Jingming Zhang、Zhixiang Wang、Zheng Fang、Kai Guo

  DOI：10.1039/c6ra19000f

  日期：——

  An effective one-pot synthesis of β-indolylketones from saturated ketones and indoles was developed. It is noteworthy that this methodology has a good functional group tolerance (alkyl, nitro, halogen, hydroxyl, methoxyl, carboxyl and ester) and is of great significance to the preparation of many indole heterocycles.

  从饱和的酮和吲哚开发了一种有效的一锅法合成β-吲哚基酮的方法。值得注意的是，该方法具有良好的官能团耐受性（烷基，硝基，卤素，羟基，甲氧基，羧基和酯），并且对许多吲哚杂环的制备具有重要意义。
• Unbiased C3‐Electrophilic Indoles: Triflic Acid Mediated C3‐Regioselective Hydroarylation of N−H Indoles**
  作者：Nazarii Sabat、Weiping Zhou、Vincent Gandon、Xavier Guinchard、Guillaume Vincent

  DOI：10.1002/anie.202204400

  日期：2022.7.25

  Direct dearomative C3-functionalization of indoles provided access to privileged scaffolds by an umpolung strategy. Against all odds, C3-indolium intermediates could be generated from NH-indoles under operationally simple conditions with triflic acid at room temperature to promote intra- and intermolecular C3-regioselective hydroarylation. DFT studies suggest that these cationic or dicationic intermediates

  吲哚的直接脱芳香 C3 功能化通过 umpolung 策略提供了获得特权支架的途径。尽管困难重重，C3-吲哚中间体可以在操作简单的条件下用三氟甲磺酸在室温下从NH-吲哚生成，以促进分子内和分子间C3区域选择性加氢芳基化。 DFT 研究表明这些阳离子或双阳离子中间体可以通过氢键簇来稳定。
• Synthesis, structure and AM1 conformational study of [3]paracyclo[3](1,3)indolophane, a novel chiral cyclophane
  作者：Graham J. Bodwell、Jiang Li、David O. Miller

  DOI：10.1016/s0040-4020(99)00792-9

  日期：1999.11

  The title compound 5 was synthesized in seven steps with an overall yield of 22%. The two bridges were formed by a conjugate addition of indole to a Michael acceptor and by an intramolecular N-alkylation, respectively. A dynamic NMR study revealed the presence of a conformational process with an activation barrier of 10.9+/-0.2 kcal/mol, which was assigned to a ring flipping process that interconverts two enantiomeric sets of equilibrating bridge conformers. In the crystal structure of 5, both bridges adopt the pseudo-chair conformation, in accord with the lowest energy conformation identified by an AM1 conformational search. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of 3,3-Spiroindolines via FeCl₃-Mediated Cyclization of Aryl- or Alkene-Containing 3-Substituted N–Ac Indoles
  作者：Raj Kumar Nandi、Régis Guillot、Cyrille Kouklovsky、Guillaume Vincent

  DOI：10.1021/acs.orglett.6b00174

  日期：2016.4.15

  the cyclization of 3-substituted N-acetylindoles for the straightforward synthesis of 3,3-spiroindolines via the Friedel–Crafts reaction of an appended aryl group or the formal [2 + 2] cycloaddition of an appended alkene. Our strategy involves an Umpolung of the C2═C3 bond of the indole nucleus during FeCl3-mediated hydroarylation or annulation reactions.

  我们报道了通过取代的芳基的弗瑞德-克来福特反应或附加的烯烃的正式[2 + 2]环加成反应，可直接合成3,3-螺二氢吲哚的3取代的N-乙酰吲哚的环化反应。我们的策略涉及在FeCl 3介导的氢化反应或环化反应中吲哚核的C2═C3键的结合。