ethyl 3-acetyl-4-cyano-9-methyl-4,9-dihydropyrano[2,3-b]indole-4-carboxylate | 1361403-87-3

• 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-acetyl-4-cyano-9-methyl-4,9-dihydropyrano[2,3-b]indole-4-carboxylate
• 英文别名: Ethyl 3-acetyl-4-cyano-9-methylpyrano[2,3-b]indole-4-carboxylate；ethyl 3-acetyl-4-cyano-9-methylpyrano[2,3-b]indole-4-carboxylate
• CAS: 1361403-87-3
• 化学式: C₁₈H₁₆N₂O₄
• 分子量: 324.336
• InChiKey: JFAVQNNRCGOVTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl (E)-1-methyl-2-oxo-3-indolinylidenecyanoacetate 、 3-丁炔-2-酮 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以71%的产率得到ethyl 3-acetyl-4-cyano-9-methyl-4,9-dihydropyrano[2,3-b]indole-4-carboxylate
  参考文献：
  名称：

  Phosphorus-containing Lewis base catalyzed highly regioselective cyclization of isatin derived electron-deficient alkenes with but-3-yn-2-one

  摘要：

  In this paper, we reported that phosphorus-containing Lewis bases catalyzed [4+2] cyclization of N-protected isatin derived electron-deficient alkenes with but-3-yn-2-one could proceed smoothly to give the corresponding dihydropyrano[2,3-b]indoles in good to excellent yields under mild conditions. The substrate scope has been carefully examined and the plausible reaction mechanism has been also proposed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.036

文献信息

• Phosphorus-containing Lewis base catalyzed highly regioselective cyclization of isatin derived electron-deficient alkenes with but-3-yn-2-one
  作者：Zhong Lian、Yin Wei、Min Shi

  DOI：10.1016/j.tet.2012.01.036

  日期：2012.3

  In this paper, we reported that phosphorus-containing Lewis bases catalyzed [4+2] cyclization of N-protected isatin derived electron-deficient alkenes with but-3-yn-2-one could proceed smoothly to give the corresponding dihydropyrano[2,3-b]indoles in good to excellent yields under mild conditions. The substrate scope has been carefully examined and the plausible reaction mechanism has been also proposed. (C) 2012 Elsevier Ltd. All rights reserved.