| 1196468-55-9

• 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
• CAS: 1196468-55-9
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: QCYRPKVTWYDARQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 碘 作用下， 以 二氯甲烷 为溶剂， 以80 %的产率得到4-iodo-3-(4-methoxyphenyl)-1H-[1,3]oxazino[3,4-a]indol-1-one
  参考文献：
  名称：

  Electrophile‐Promoted Nucleophilic Cyclization of 2‐Alkynylindoles to Give 4‐Substituted Oxazinoindolones

  摘要：

  AbstractA method for the synthesis of 4‐organoselanyl oxazinoindolone derivatives by the cascade cyclization of N‐(alkoxycarbonyl)‐2‐alkynylindoles using iron(III) chloride and diorganyl diselenides as promoters was developed. This protocol was applied to a series of N‐(alkoxycarbonyl)‐2‐alkynylindoles containing different substituents. The reaction conditions also tolerated a variety of diorganyl diselenides having both electron donating and electron withdrawing groups. However, the reaction did not work for diorganyl disulfides and ditellurides. The reaction mechanism seems to proceed via an ionic pathway and the cooperative action between iron(III) chloride and diorganyl diselenides is crucial for successful cyclization. We also found that using the same starting materials, by simply changing the electrophilic source to iodine, led to the formation of 4‐iodo‐oxazinoindolones. The high reactivity of Csp2−Se and Csp2−I bonds were tested under cross‐coupling conditions leading to the preparation of a new class of functionalized indole derivatives. In addition, the absorption, emission and electrochemical properties of 4‐organoselanyl oxazinoindolones showed an important relationship with the substituents of the aromatic rings. The advantages of the methodology include the use of electrophilic to promote the cyclization reaction and functionalization of the indole ring, and the electronic properties presented by the prepared compounds can be exploited as probes, analyte detectors and optical materials.

  DOI：

  10.1002/chem.202202847
• 作为产物：
  描述：

  ethyl 2-(((trifluoromethyl)sulfonyl)oxy)-1H-indole-1-carboxylate 、 4-乙炔基苯甲醚 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  Novel Domino Approach to Fluorescent Pyrimido[1,6-a]indolones

  摘要：

  易于获取的N-乙氧基碳酰基-2-烷基炔基吲哚在初级芳基胺存在下，经过TiCl4/t-BuNH2催化，发生多步水氨化-环化反应，得到吡啶[1,6-a]吲哚酮，产率良好到优秀。该反应涉及初始的高度区域和化学选择性的水氨化反应。获得的化合物显示出有趣的荧光特性，可以代表一类新的有用的生物分析标记物。

  DOI：

  10.1055/s-0029-1217807