7-cinnamylindole | 1219637-86-1

• 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-cinnamylindole
• CAS: 1219637-86-1
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: HVVQRQHOLYPRFF-UHFFFAOYSA-N

物化性质

• 沸点：
  420.6±14.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  15.79
• 氢给体数：
  1.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  乙酸桂酯 、 7-吲哚硼酸频那醇酯 在 potassium fluoride 、 三(2-呋喃基)膦 、 palladium dichloride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以52%的产率得到7-cinnamylindole
  参考文献：
  名称：

  Iridium-Catalyzed, Silyl-Directed Borylation of Nitrogen-Containing Heterocycles

  摘要：

  Selective methods for the functionalization of indoles and other nitrogen heterocycles would provide access to the core structures of many natural products and pharmaceuticals. Although there are many methods and strategies for the synthesis of substituted indoles or functionalization of the azole ring, strategies for the selective functionalization of the benzo-fused portion of the indole skeleton, particularly the 7-position, are less common. We report a one-pot, iridium-catalyzed, silyl-directed C-H borylation of indoles at the 7-position. This process occurs in high yield with a variety of substituted indoles, and conversions of the 7-borylindole products to 7-aryl-, 7-cinnamyl-, and 7-haloindoles are demonstrated. The Ir-catalyzed, silyl-directed C-H borylation also occurs with several other nitrogen heterocycles, including carbazole, phenothiazines, and tetrahydroquinoline. The utility of this methodology is highlighted by the one-pot synthesis of a member of the pyrrolophenanthridone class of alkaloid natural products.

  DOI：

  10.1021/ja1006405

文献信息

• Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the allylation of aryl halides with allylic alcohols
  作者：Xue-Gong Jia、Peng Guo、Jicheng Duan、Xing-Zhong Shu

  DOI：10.1039/c7sc03140h

  日期：——

  selectively. The reaction tolerates a wide range of functional groups (e.g. silanes, boronates, anilines, esters, alcohols, and various heterocycles) and works with various allylic alcohols. Complementary to most current routes for the C3 allylation of an unprotected indole, this method provides access to C2 and C4–C7 allylated indoles. Preliminary mechanistic experiments reveal that the reaction might start

  控制交叉亲电偶联反应的选择性是一项重大挑战，特别是当一种亲电试剂反应性更强时。我们报告了一种通用且实用的策略，通过镍和路易斯酸催化的组合来解决反应性和非反应性亲电试剂之间的反应中的这个问题。该策略用于将芳基卤化物与烯丙醇偶联以选择性地形成线性烯丙芳​​烃。该反应耐受广泛的官能团（例如硅烷、硼酸盐、苯胺、酯、醇和各种杂环）并与各种烯丙醇一起使用。作为对未受保护的吲哚的 C3 烯丙基化的大多数当前路线的补充，该方法提供了对 C2 和 C4-C7 烯丙基化吲哚的访问。初步的机理实验表明，该反应可能从芳基镍中间体开始，然后在 Mn 存在下与路易斯酸活化的烯丙醇反应。