4-[5,6-dimethoxy-1-(4-methylphenylsulfonyl)-3-phenyl-1H-2-indolyl]-2-butanone | 309927-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-[5,6-dimethoxy-1-(4-methylphenylsulfonyl)-3-phenyl-1H-2-indolyl]-2-butanone
• 英文别名: N-tosyl-2-(3-oxobutyl)-3-phenyl-5,6-dimethoxyindole；4-{5,6-dimethoxy-1-[(4-methylphenyl)sulfonyl]-3-phenyl-1H-indol-2-yl}butan-2-one；4-[5,6-dimethoxy-1-(4-methylphenyl)sulfonyl-3-phenylindol-2-yl]butan-2-one
• CAS: 309927-66-0
• 化学式: C₂₇H₂₇NO₅S
• 分子量: 477.581
• InChiKey: KECQTBUQLTUKJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[5,6-dimethoxy-1-(4-methylphenylsulfonyl)-3-phenyl-1H-2-indolyl]-2-butanone 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到4-(5,6-dimethoxy-3-phenyl-1H-2-indolyl)-2-butanone
  参考文献：
  名称：

  Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction

  摘要：

  A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.056
• 作为产物：
  描述：

  3,4-二甲氧基二苯甲酮 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 硝酸 、 铁粉 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 7.5h， 生成 4-[5,6-dimethoxy-1-(4-methylphenylsulfonyl)-3-phenyl-1H-2-indolyl]-2-butanone
  参考文献：
  名称：

  Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction

  摘要：

  A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.056

文献信息

• Brönsted Acid-Catalyzed One-Pot Synthesis of Indoles from <i>o</i>-Aminobenzyl Alcohols and Furans
  作者：Alexey Kuznetsov、Anton Makarov、Aleksandr E. Rubtsov、Alexander V. Butin、Vladimir Gevorgyan

  DOI：10.1021/jo402132p

  日期：2013.12.6

  Brönsted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans has been developed. This method operates via the in situ formation of aminobenzylfuran, followed by its recyclization into the indole core. The method proved to be efficient for substrates possessing different functional groups, including −OMe, −CO2Cy, and −Br. The resulting indoles can easily be transformed

  已经开发出布朗斯台德酸催化从邻氨基苯甲醇和呋喃一锅合成吲哚的方法。该方法通过原位形成氨基苄基呋喃，然后将其再循环到吲哚核心中来进行。该方法被证明对于具有不同官能团的底物是有效的，包括-OMe、-CO 2 Cy和-Br。所得吲哚可以很容易地转化为不同的支架，包括2,3-和1,2-融合吲哚，以及在C-2位置具有α,β-不饱和酮部分的吲哚。
• Furan ring opening—indole ring closure: a new modification of the Reissert reaction for indole synthesis
  作者：Alexander V Butin、Tat‘yana A Stroganova、Irina V Lodina、Gennady D Krapivin

  DOI：10.1016/s0040-4039(01)00066-1

  日期：2001.3

  A new modification of the Reissert reaction is reported. On treatment of 2-tosylaminobenzylfurans with ethanolic HCl, some indole derivatives have been obtained. The furan ring served as the origin of a carbonyl group in this reaction.

  据报道，对Reissert反应进行了新的修饰。用乙醇HCl处理2-甲苯磺酰基苄基呋喃后，已经获得了一些吲哚衍生物。呋喃环用作该反应中羰基的来源。
• Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction
  作者：Alexander V. Butin、Sergey K. Smirnov、Tatyana A. Stroganova、Wolfgang Bender、Gennady D. Krapivin

  DOI：10.1016/j.tet.2006.10.056

  日期：2007.1

  A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus. (c) 2006 Elsevier Ltd. All rights reserved.