1-(thiophen-2-yl)-1H-indole | 131579-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(thiophen-2-yl)-1H-indole
• 英文别名: N-(2-thienyl)indole；1-Thiophen-2-ylindole
• CAS: 131579-04-9
• 化学式: C₁₂H₉NS
• 分子量: 199.276
• InChiKey: IBKAUALXZXRNLU-UHFFFAOYSA-N

物化性质

• 沸点：
  338.7±24.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  33.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(thiophen-2-yl)-1H-indole 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 Methyl 2-oxo-2-(1-thiophen-2-ylindol-3-yl)acetate
  参考文献：
  名称：

  Novel Indolylindazolylmaleimides as Inhibitors of Protein Kinase C-β:  Synthesis, Biological Activity, and Cardiovascular Safety

  摘要：

  Novel indolylindazolylmaleimides were synthesized and examined for kinase inhibition. We identified low-nanomolar inhibitors of PKC-beta with good to excellent selectivity vs other PKC isozymes and GSK-3 beta. In a cell-based functional assay, 8f and 8i effectively blocked IL-8 release induced by PKC-beta II (IC50 = 20-25 nM). In cardiovascular safety assessment, representative lead compounds bound to the hERG channel with high affinity, potently inhibited ion current in a patch-clamp experiment, and caused a dose-dependent increase of QT(c) in guinea pigs.

  DOI：

  10.1021/jm049478u
• 作为产物：
  描述：

  2-溴噻吩 、 吲哚 在 copper(I) oxide 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 1.0h， 以85%的产率得到1-(thiophen-2-yl)-1H-indole
  参考文献：
  名称：

  通过微波辅助的无配体铜催化的N-化使吲哚多样化

  摘要：

  开发了一种简单，高效的微波辐射下的Cu 2 O催化剂体系，用于各种没有配体和添加剂的吲哚的N-芳基化。通过在1小时内将吲哚与各种杂芳基卤化物偶合，可以制备出各种N-杂芳基化的吲哚。溴吲哚与芳基碘的选择性反应提供了N-芳基溴吲哚，这可能是钯催化的Heck和Suzuki偶联反应的有用中间体。

  DOI：

  10.1002/bkcs.10995

文献信息

• Metal-free regioselective C-3 acetoxylation of N-substituted indoles: crucial impact of nitrogen-substituent
  作者：Vineeta Soni、Ulhas N. Patel、Benudhar Punji

  DOI：10.1039/c5ra10428a

  日期：——

  A metal-free method for the regioselective C-3 acetoxylation of the N-substituted indoles with PhI(OAc)2 is described under mild reaction conditions. This method tolerates a broad range of functional groups with moderate to good yields. The π-electron-deficient aryl-substituents on the N-atom of indoles and the acidic reaction medium remarkably favor C-3 acetoxylation.

  描述了在温和的反应条件下用PhI（OAc）2对N取代的吲哚进行区域选择性C-3乙酰氧基化的无金属方法。该方法可耐受多种官能团，并具有中等至良好的产率。吲哚的N原子上的π电子不足的芳基取代基和酸性反应介质显着促进了C-3的乙酰氧基化。
• N-Arylations of Nitrogen-Containing Heterocycles with Aryl and Heteroaryl Halides Using a Copper(I) Oxide Nanoparticle/1,10-Phenanthroline Catalytic System
  作者：Jin-Heng Li、Bo-Xiao Tang、Sheng-Mei Guo、Man-Bo Zhang

  DOI：10.1055/s-2008-1067014

  日期：2008.6

  and indoles, with aryl and heteroaryl halides catalyzed by copper(I) oxide (Cu 2 O) nanoparticles is demonstrated. Four types of Cu 2 O were evaluated: the bulky compound and its cubic, octahedral, and spherical nanoparticulate forms. The results show that Cu 2 O nanoparticles, in particular the cubic form, are highly efficient for the N-arylation reaction. In the presence of cubic Cu 2 O nanoparticles

  演示了含氮杂环（即咪唑、三唑和吲哚）的无溶剂 N-芳基化的一般程序，其中芳基和杂芳基卤化物由氧化铜 (I) (Cu 2 O) 纳米颗粒催化。评估了四种类型的 Cu 2 O：大体积化合物及其立方、八面体和球形纳米颗粒形式。结果表明，Cu 2 O 纳米颗粒，特别是立方形式，对 N-芳基化反应非常有效。在立方 Cu 2 O 纳米粒子、1,10-菲咯啉和四丁基氟化铵存在下，多种含氮杂环在 110-145 °C 下与芳基和杂芳基卤化物顺利进行 N-芳基化反应，得到相应的产物以优异的产量。值得注意的是，该反应是在无溶剂条件下进行的。
• Immobilized Pd(0) nanoparticles on phosphine-functionalized graphene as a highly active catalyst for Heck, Suzuki and N-arylation reactions
  作者：Reza Fareghi-Alamdari、Mohsen G. Haqiqi、Negar Zekri

  DOI：10.1039/c5nj02227d

  日期：——

  Phosphine functionalized graphene was used for the immobilization of Pd nanoparticles and utilized in C–C and C–N bond formation reactions.

  磷化功能化石墨烯被用于固定Pd纳米颗粒，并应用于C-C和C-N键形成反应。
• CuI/8-Hydroxyquinalidine Promoted N-Arylation of Indole and Azoles
  作者：Xinye Yang、Hui Xing、Ye Zhang、Yisheng Lai、Yihua Zhang、Yongwen Jiang、Dawei Ma

  DOI：10.1002/cjoc.201100433

  日期：2012.4

  An efficient catalytic system of CuI/8‐hydroxyquinalidine was developed for the coupling of aryl iodides and indole as well as some azoles. The reaction could be carried out at 90°C under the condition of relatively low catalyst loading, affording various N‐arylindoles and N‐aryl azoles in good yields. The functionalized and hindered aryl iodides were suitable substrates for this transformation.

  开发了一种有效的CuI / 8-羟基喹啉催化体系，用于偶合芳基碘化物和吲哚以及某些唑类。该反应可以在90℃下相对低的催化剂负载的条件下进行，得到各种Ñ -arylindoles和ñ -芳基以良好产率唑类。官能化和受阻的芳基碘化物是该转化的合适底物。
• Palladium-Catalyzed Three-Component Regioselective Dehydrogenative Coupling of Indoles, 2-Methylbut-2-ene, and Carboxylic Acids
  作者：Xing-Long Zhang、Rui-Li Guo、Meng-Yue Wang、Bao-Yin Zhao、Qiong Jia、Jin-Hui Yang、Yong-Qiang Wang

  DOI：10.1021/acs.orglett.1c03776

  日期：2021.12.17

  Five-carbon (C5) structural units are the fundamental building blocks of many natural products. An unprecedented palladium-catalyzed three-component dehydrogenative cascade coupling of indoles, 2-methylbut-2-ene, and carboxylic acids has been developed. The approach enables the straightforward introduction of a C3′-bonded five-carbon structural unit with a tertiary alcohol quaternary carbon center

  五碳 (C5) 结构单元是许多天然产品的基本组成部分。已经开发出一种前所未有的钯催化的吲哚、2-甲基丁-2-烯和羧酸的三组分脱氢级联偶联。该方法能够将具有叔醇季碳中心的 C3' 键合五碳结构单元直接引入吲哚中。该协议采用 2-甲基丁-2-烯作为 C5 源，具有广泛的底物范围、原子和步骤经济以及高化学和区域选择性。