1-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 1-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridine
• 英文别名: N-(3-thienyl)-7-azaindole；1-Thiophen-3-ylpyrrolo[2,3-b]pyridine；1-thiophen-3-ylpyrrolo[2,3-b]pyridine
• 化学式: C₁₁H₈N₂S
• 分子量: 200.264
• InChiKey: SBHIPBOEUGLRFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridine 、 丙烯酸丁酯 在 tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate 、 silver(I) acetate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 3.0h， 以67%的产率得到butyl (E)-3-(3-(1H-pyrrolo[2,3-b]pyridin-1-yl)thiophen-2-yl)acrylate
  参考文献：
  名称：

  Rhodium(III)-catalyzed Mono- and Dialkenylation of N-Phenyl-7-azaindoles via Regioselective C–H Bond Cleavage

  摘要：

  在铑(III)催化下，N-苯基-7-氮杂吲哚与烯烃的区域选择性单烯丙基化和二烯丙基化反应得以高效进行。此外，还可以实现非对称二烯丙基苯衍生物的一锅合成。一些烯化产物显示出固态荧光。

  DOI：

  10.1246/cl.160234
• 作为产物：
  描述：

  3-溴噻吩 、 7-氮杂吲哚 在 copper(l) iodide 、 potassium carbonate 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以40%的产率得到1-(thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  N-Arylation of azaindoles in LiCl-mediated catalytic CuI reactions

  摘要：

  N-Arylation of 5- and 7-azaindoles was achieved in LiCl-mediated catalytic Cul reactions at 120 degrees C with moderate to high yields. N-Arylation can be performed with various arylhalides, such as phenyl, pyridine, quinotine, thiophen, and thiazole moieties. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.05.062

文献信息

• A manganese/copper bimetallic catalyst for C–N coupling reactions under mild conditions in water
  作者：Yong-Chua Teo、Fui-Fong Yong、Gina Shiyun Lim

  DOI：10.1016/j.tetlet.2011.10.128

  日期：2011.12

  An efficient and convenient bimetallic MnF2/CuI catalyst in combination with trans-1,2-diaminocyclohexane has been developed for the cross-coupling of nitrogen heterocycles with aryl halides in water at moderate temperature. A variety of nitrogen nucleophiles including pyrazole, 7-azaindole, indazole, indole, pyrrole and imidazole afforded the corresponding products in moderate to good yields (up to

  已经开发了一种有效且方便的双金属MnF 2 / CuI催化剂与反式-1,2-二氨基环己烷的组合，用于在中等温度下氮杂环与芳基卤化物的交叉偶联。在所述芳基化条件下，包括吡唑，7-氮杂吲哚，吲唑，吲哚，吡咯和咪唑在内的各种氮亲核试剂以中等至良好的收率（最高达94％）提供了相应的产物。
• Cobalt(III)-Catalyzed C–H Amidation of 7-Azaindoles with Dioxazolones: Synthesis of 7-Azaindole Amidated Derivatives
  作者：Jun-Shu Sun、Man Liu、Jing Zhang、Lin Dong

  DOI：10.1021/acs.joc.8b01354

  日期：2018.9.7

  An efficient cobalt-catalyzed C–H amidation of 7-azaindoles was developed by using dioxazolones as the amidating reagent. A wide scope of substituted 7-azaindoles, even N-vinly groups, is suitable for the reaction, generating 7-azaindoles derivatives with potential properties up to 91% yield under straightforward and strong applicable reaction conditions.

  通过使用重氮唑酮作为酰胺化试剂，开发了一种高效的钴催化的7-氮杂吲哚的CH酰胺化反应。各种各样的取代的7-氮杂吲哚，甚至是N-乙烯基均适用于该反应，在直接而强大的适用反应条件下，生成具有高达91％收率的潜在性质的7-氮杂吲哚衍生物。
• Manganese-Mediated N-Heteroarylation of Indoles and Indazoles in Water
  作者：Yong-Chua Teo、Fui-Fong Yong

  DOI：10.1055/s-0032-1316682

  日期：2012.9

  A convenient strategy for the N-heteroarylation of indoles and indazoles using MnF2/trans-1,2-diaminocyclohexane as catalyst and cesium carbonate as the base in water has been developed. The protocol afforded the corresponding N-heteroarylated products in moderate to good yields (up to 90%).
• N-Arylation of azaindoles in LiCl-mediated catalytic CuI reactions
  作者：Chang Sung Hong、Jae Young Seo、Eul Kgun Yum

  DOI：10.1016/j.tetlet.2007.05.062

  日期：2007.7

  N-Arylation of 5- and 7-azaindoles was achieved in LiCl-mediated catalytic Cul reactions at 120 degrees C with moderate to high yields. N-Arylation can be performed with various arylhalides, such as phenyl, pyridine, quinotine, thiophen, and thiazole moieties. (c) 2007 Published by Elsevier Ltd.
• Rhodium(III)-catalyzed Mono- and Dialkenylation of <i>N</i>-Phenyl-7-azaindoles via Regioselective C–H Bond Cleavage
  作者：Ryosuke Morioka、Tetsuya Satoh、Masahiro Miura

  DOI：10.1246/cl.160234

  日期：2016.6.5

  Rhodium-catalyzed regioselective mono- and dialkenylation reactions of N-phenyl-7-azaindoles with alkenes proceed efficiently under rhodium(III) catalysis. The one-pot synthesis of unsymmetrically dialkenylated benzene derivative can also be achieved. Some of the alkenylated products exhibit solid-state fluorescence.

  在铑(III)催化下，N-苯基-7-氮杂吲哚与烯烃的区域选择性单烯丙基化和二烯丙基化反应得以高效进行。此外，还可以实现非对称二烯丙基苯衍生物的一锅合成。一些烯化产物显示出固态荧光。