7-(2-(trimethylsilyl)ethynyl)-1H-indole | 1159414-14-8

• 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: 7-(2-(trimethylsilyl)ethynyl)-1H-indole
• 英文别名: 2-(1H-indol-7-yl)ethynyl-trimethylsilane
• CAS: 1159414-14-8
• 化学式: C₁₃H₁₅NSi
• 分子量: 213.354
• InChiKey: UYORIWCBBUPKMK-UHFFFAOYSA-N

物化性质

• 沸点：
  314.8±24.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  7-(2-(trimethylsilyl)ethynyl)-1H-indole 在 甲醇 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到7-ethynyl-1H-indole
  参考文献：
  名称：

  Diels−Alder Reactions of Cyclopentadienones with Aryl Alkynes To Form Biaryl Compounds

  摘要：

  Diels-Alder reactions of cyclopentadienones, to afford substituted biaryls, were studied using an expanded substrate base. Electron-withdrawing groups on the aryl alkyne dienophile facilitated the reaction, and these substrates gave better yields than those with electron-donating substituents. Steric effects were also found to be important, and o,o'-dimethylphenylacetylene gave much poorer yield of biaryl product.

  DOI：

  10.1021/jo900559n
• 作为产物：
  描述：

  乙烯基溴化镁 、 三甲基((2-硝基苯基)乙炔)硅烷 在 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 以35%的产率得到7-(2-(trimethylsilyl)ethynyl)-1H-indole
  参考文献：
  名称：

  Diels−Alder Reactions of Cyclopentadienones with Aryl Alkynes To Form Biaryl Compounds

  摘要：

  Diels-Alder reactions of cyclopentadienones, to afford substituted biaryls, were studied using an expanded substrate base. Electron-withdrawing groups on the aryl alkyne dienophile facilitated the reaction, and these substrates gave better yields than those with electron-donating substituents. Steric effects were also found to be important, and o,o'-dimethylphenylacetylene gave much poorer yield of biaryl product.

  DOI：

  10.1021/jo900559n

文献信息

• Ni‐Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights
  作者：Ryu Yamasaki、Masato Ohashi、Kyotaro Maeda、Takuya Kitamura、Minami Nakagawa、Korehito Kato、Tetsushi Fujita、Ryohei Kamura、Kazuto Kinoshita、Hyuma Masu、Isao Azumaya、Sensuke Ogoshi、Shinichi Saito

  DOI：10.1002/chem.201204087

  日期：2013.3.4

  A detailed study of the Ni‐catalyzed [4+3+2] cycloaddition reaction between ethyl cyclopropylideneacetate and dienynes has been conducted, resulting in the development of a new method for the synthesis of compounds containing nine‐membered rings. We studied the reactivity of various dienynes, together with their substituent and conformational effects. The mechanism of the reaction was probed by examining

  进行了Ni催化的[4 + 3 + 2]环丙基亚乙基乙酸乙酯与二烯酮之间环加成反应的详细研究，从而开发了一种新的合成含九元环化合物的新方法。我们研究了各种二烯的反应性，以及它们的取代基和构象效应。通过检查Ni配合物和二烯的化学计量反应来探究该反应的机理。
• Highly Enantioselective Rhodium(I)-Catalyzed Alder-ene-type Cycloisomerization of 1,7-Enynes
  作者：Jingwen Zeng、Wei Fang、Bijin Lin、Gen-Qiang Chen、Xumu Zhang

  DOI：10.1021/acs.orglett.1c04171

  日期：2022.1.28

  asymmetric cycloisomerization of 1,7-enynes is regarded as a formidable challenge due to the poor ability of 1,7-enynes to serve as bidentate ligands to metal. In this Letter, a highly enantioselective rhodium(I)-catalyzed Alder-ene-type cycloisomerization of 1,7-enynes is disclosed, offering an efficient method for the synthesis of a wide range of fused six-membered cyclic compounds. Furthermore, a high

  由于 1,7-烯炔作为金属双齿配体的能力差，过渡金属催化的 1,7-烯炔不对称环异构化被认为是一项艰巨的挑战。在这封信中，公开了一种高度对映选择性的铑 (I) 催化的 1,7-烯炔的 Alder-ene 型环异构化，为合成各种稠合六元环状化合物提供了一种有效的方法。此外，还进行了高周转频率实验和氘标记实验，以深入了解这种转变。
• Diels−Alder Reactions of Cyclopentadienones with Aryl Alkynes To Form Biaryl Compounds
  作者：Anthony J. Pearson、Yan Zhou

  DOI：10.1021/jo900559n

  日期：2009.6.5

  Diels-Alder reactions of cyclopentadienones, to afford substituted biaryls, were studied using an expanded substrate base. Electron-withdrawing groups on the aryl alkyne dienophile facilitated the reaction, and these substrates gave better yields than those with electron-donating substituents. Steric effects were also found to be important, and o,o'-dimethylphenylacetylene gave much poorer yield of biaryl product.