ethyl 3-cyano-4-phenylmethoxy-1H-indole-7-carboxylate | 1313530-07-2

• 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: ethyl 3-cyano-4-phenylmethoxy-1H-indole-7-carboxylate
• CAS: 1313530-07-2
• 化学式: C₁₉H₁₆N₂O₃
• 分子量: 320.348
• InChiKey: YLCWFUQIYQGHDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-溴-3-硝基苯酚 在 1,1'-双(二苯基膦)二茂铁 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 丙酮 、 乙腈 为溶剂， 130.0 ℃ 、3.5 MPa 条件下， 生成 ethyl 3-cyano-4-phenylmethoxy-1H-indole-7-carboxylate
  参考文献：
  名称：

  Rapid synthesis of diversely functionalized 3,4,7-trisubstituted indoles

  摘要：

  Synthetic approaches are described for the synthesis of 4-alkoxyindole-7-carboxamides and 4-alkoxy-3-cyanoindole-7-carboxamides, which are useful intermediates in medicinal chemistry research. Two strategies were employed, highlighted by a Bartoli indole synthesis ora sequential and regioselective use of chlorosulfonyl isocyanate to install both the 3-cyano and 7-carboxamido groups. These routes are scalable and afford diversely functionalized indoles for further elaboration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.086

文献信息

• Rapid synthesis of diversely functionalized 3,4,7-trisubstituted indoles
  作者：Seth W. Grant、Timothy F. Gallagher、Mark A. Bobko、Celine Duquenne、Jeffrey M. Axten

  DOI：10.1016/j.tetlet.2011.04.086

  日期：2011.6

  Synthetic approaches are described for the synthesis of 4-alkoxyindole-7-carboxamides and 4-alkoxy-3-cyanoindole-7-carboxamides, which are useful intermediates in medicinal chemistry research. Two strategies were employed, highlighted by a Bartoli indole synthesis ora sequential and regioselective use of chlorosulfonyl isocyanate to install both the 3-cyano and 7-carboxamido groups. These routes are scalable and afford diversely functionalized indoles for further elaboration. (C) 2011 Elsevier Ltd. All rights reserved.