4-(1H-indol-3-yl)-1-phenylbutan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1H-indol-3-yl)-1-phenylbutan-1-one
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: CEKJMOMIUVOOOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(1H-indol-3-yl)-1-phenylbutan-1-one 在 sodium tetrahydroborate 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.5h， 生成 1-苯基咔唑
  参考文献：
  名称：

  TfOH催化的1取代四氢咔唑的合成

  摘要：

  1-取代的四氢咔唑的合成是通过TfOH催化的与仲和叔醇连接的3-取代的吲哚的反应来完成的。该反应被推广用于多种底物，并扩展到2,3,3a，6-四氢-1 H-吡啶并[3,2,1- jk ]咔唑和咔唑的合成。

  DOI：

  10.1016/j.tetlet.2018.07.023
• 作为产物：
  描述：

  3-吲哚丁酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-(1H-indol-3-yl)-1-phenylbutan-1-one
  参考文献：
  名称：

  TfOH催化的1取代四氢咔唑的合成

  摘要：

  1-取代的四氢咔唑的合成是通过TfOH催化的与仲和叔醇连接的3-取代的吲哚的反应来完成的。该反应被推广用于多种底物，并扩展到2,3,3a，6-四氢-1 H-吡啶并[3,2,1- jk ]咔唑和咔唑的合成。

  DOI：

  10.1016/j.tetlet.2018.07.023

文献信息

• Strong and Confined Acids Catalyze Asymmetric Intramolecular Hydroarylations of Unactivated Olefins with Indoles
  作者：Pinglu Zhang、Nobuya Tsuji、Jie Ouyang、Benjamin List

  DOI：10.1021/jacs.0c12042

  日期：2021.1.20

  asymmetric hydroarylations of activated, electron-poor olefins with activated, electron-rich arenes have been described. In contrast, only a few approaches that can handle unactivated, electronically neutral olefins have been reported and invariably require transition metal catalysts. Here we show how an efficient and highly enantioselective catalytic asymmetric intramolecular hydroarylation of aliphatic

  近年来，已经描述了几种活化的贫电子烯烃与活化的富电子芳烃的有机催化不对称氢化芳基化。相比之下，只有少数方法可以处理未活化的电子中性烯烃，并且总是需要过渡金属催化剂。在这里，我们展示了如何使用强且受限的 IDPi 布朗斯台德酸催化剂实现脂肪族和芳香族烯烃与吲哚的高效且高度对映选择性催化不对称分子内加氢芳基化。这种前所未有的转化是由叔碳正离子形成实现的，并以优异的对映选择性和广泛的底物范围建立了四元立体中心，包括脂肪族碘化物、叠氮化物和烷基硼酸酯，
• Synthesis of 2-(3′-Indolyl)tetrahydrofurans by Oxidative Cycloetherification
  作者：Rachel M. Gillard、Jonathan Sperry

  DOI：10.1021/acs.joc.5b00112

  日期：2015.3.6

  A series of 2-(3'-indolyl)tetrahydrofurans have been prepared by a DDQ-mediated oxidative cycloetherification process. Performing the reaction under biphasic conditions prevents reductive cleavage of the products by the spent oxidant (DDQH(2)).
• The first example of the C-3 alkylation of indoles with cyclopropyl ketones promoted by CeCl3·7H2O/LiI
  作者：J.S. Yadav、B.V. Subba Reddy、D. Chandrakanth、G. Satheesh

  DOI：10.1016/j.tetlet.2007.09.023

  日期：2007.11

  Indoles undergo smooth alkylation with cyclopropyl ketones in the presence of the CeCl3 center dot 7H(2)O/LiI reagent system in refluxing acetonitrile under neutral conditions to produce the corresponding C-3 substituted indole derivatives in good to high yields and with high selectivity. The use of CeCl3 7H(2)O/LiI makes this method simple, convenient, and cost-effective. (C) 2007 Elsevier Ltd. All rights reserved.
• A Combined Theoretical and Experimental Investigation into the Highly Stereoselective Migration of Spiroindolenines
  作者：Chao Zheng、Qing-Feng Wu、Shu-Li You

  DOI：10.1021/jo400365e

  日期：2013.5.3

  This paper describes a combined theoretical and experimental investigation into the acid-catalyzed migration of spiroindolenines to the corresponding fused cyclic products. It is suggested that the "three-center-two-electron"-type transition state is the crucial reason accounting for the highly stereoselective phenomenon. Further studies demonstrated that the electronic property of the migratory group as well as the ring size may have a major influence on the reaction profile of the migration process. Some predictions based on the computational results were supported by additional experiments.
• TfOH catalyzed synthesis of 1-substituted tetrahydrocarbazoles
  作者：Laxmi Narayan Nanda、Vipin Ashok Rangari

  DOI：10.1016/j.tetlet.2018.07.023

  日期：2018.8

  Synthesis of 1-substituted tetrahydrocarbazole is accomplished by TfOH catalyzed reaction of 3-substituted indoles tethered with secondary and tertiary alcohols. The reaction was generalized for a variety of substrates and was extended to the synthesis of 2,3,3a,6-tetrahydro-1H-pyrido[3,2,1-jk]carbazole and carbazoles.

  1-取代的四氢咔唑的合成是通过TfOH催化的与仲和叔醇连接的3-取代的吲哚的反应来完成的。该反应被推广用于多种底物，并扩展到2,3,3a，6-四氢-1 H-吡啶并[3,2,1- jk ]咔唑和咔唑的合成。