1-(1-(4-methoxyphenyl)vinyl)-1H-indole | 1440537-83-6

• 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-(1-(4-methoxyphenyl)vinyl)-1H-indole
• 英文别名: 1-[1-(4-Methoxyphenyl)ethenyl]indole
• CAS: 1440537-83-6
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: RMXJNCVPOYLYGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对甲氧基苯乙酮 在 bis-triphenylphosphine-palladium(II) chloride 、 氧气 、 lithium tert-butoxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 1-(1-(4-methoxyphenyl)vinyl)-1H-indole
  参考文献：
  名称：

  Palladium-Catalyzed Oxidative Cross-Coupling of N-Tosylhydrazones with Indoles: Synthesis of N-Vinylindoles

  摘要：

  A general and efficient palladium-catalyzed oxidative cross-coupling reaction of N-tosylhydrazones with indoles providing N-vinylindoles has been developed. The reaction proceeds smoothly with various indoles and N-tosylhydrazones in a stereocontrolled manner, and a wide variety of N-vinylindoles were obtained up to 99% yields for 26 examples.

  DOI：

  10.1021/ol401217h

文献信息

• Synthesis of Terminal <i>N</i> ‐Vinylazoles from Aromatic Aldehydes, DMSO, and Azoles Based DMSO as Terminal Carbon Synthon
  作者：Zhiwen Nie、Huifang Lv、Hui Li、Miaodong Su、Tonglin Yang、Weiping Luo、Qiang Liu、Cancheng Guo

  DOI：10.1002/adsc.202100663

  日期：2021.10.5

  A protocol for the synthesis of terminal N-vinylazoles from aromatic aldehydes, DMSO, and azoles has been reported. In this strategy, DMSO was involved in the construction of the C=C bond as a terminal carbon synthon. Both aromatic aldehydes and azoles could be well tolerated and give the corresponding terminal N-vinylazoles in 52–91% yields. Based on preliminary experiments, a plausible mechanism

  已经报道了从芳香醛、DMSO 和唑类合成末端N-乙烯基唑的方案。在该策略中，DMSO 作为末端碳合成子参与了 C=C 键的构建。芳香醛和唑类都具有良好的耐受性，并以 52-91% 的产率得到相应的末端N-乙烯基唑。在初步实验的基础上，提出了一个合理的机制。
• Vinylation of N-Heteroarenes through Addition/Elimination Reactions of Vinyl Selenones
  作者：Martina Palomba、Italo Franco Coelho Dias、Michelangelo Cocchioni、Francesca Marini、Claudio Santi、Luana Bagnoli

  DOI：10.3390/molecules28166026

  日期：——

  A new protocol for the synthesis of N-vinyl azoles using vinyl selenones and azoles in the presence of potassium hydroxide was developed. This reaction proceeded under mild and transition metal-free conditions through an addition/elimination cascade process. Both aromatic and aliphatic vinyl selenones and various mono-, bi- and tri-cyclic azoles can be tolerated and give terminal N-vinyl azoles in

  开发了一种在氢氧化钾存在下使用乙烯基硒酮和唑类合成 N-乙烯基唑类的新方案。该反应在温和且不含过渡金属的条件下通过加成/消除级联过程进行。芳香族和脂肪族乙烯基硒酮以及各种单环、双环和三环唑都可以耐受，并以中等至高产率产生末端 N-乙烯基唑。还提出了一种合理的机制。