(E)-3-(1H-indol-3-yl)cyclooct-2-enone

• 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: (E)-3-(1H-indol-3-yl)cyclooct-2-enone
• 英文别名: (2E)-3-(1H-indol-3-yl)cyclooct-2-en-1-one
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: IBPOJIAQRHPGFU-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-(1H-indol-3-yl)cyclooct-2-enone 在 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  New 3-vinylation products of indole and investigation of its Diels–Alder reactivity: synthesis of unusual Morita–Baylis–Hillman-type products

  摘要：

  3-Vinylindoles as precursors of carbazole and bis-indole derivatives were synthesized. Then, to form new carbazoles, Diels-Alder reactivity of these vinylindoles was studied with various dienophiles. During the cycloaddition reaction, unusual Morita-Baylis-Hillman-type products were observed. The structure and the formation mechanism of the products is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.081
• 作为产物：
  描述：

  (2S(R),3R(S))-2-bromo-3-(1H-indol-3-yl)cyclooctanone 在 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以15%的产率得到(E)-3-(1H-indol-3-yl)cyclooct-2-enone
  参考文献：
  名称：

  New 3-vinylation products of indole and investigation of its Diels–Alder reactivity: synthesis of unusual Morita–Baylis–Hillman-type products

  摘要：

  3-Vinylindoles as precursors of carbazole and bis-indole derivatives were synthesized. Then, to form new carbazoles, Diels-Alder reactivity of these vinylindoles was studied with various dienophiles. During the cycloaddition reaction, unusual Morita-Baylis-Hillman-type products were observed. The structure and the formation mechanism of the products is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.081

文献信息

• New 3-vinylation products of indole and investigation of its Diels–Alder reactivity: synthesis of unusual Morita–Baylis–Hillman-type products
  作者：Ali Enis Sadak、Tayfun Arslan、Neslihan Celebioglu、Nurullah Saracoglu

  DOI：10.1016/j.tet.2010.02.081

  日期：2010.4

  3-Vinylindoles as precursors of carbazole and bis-indole derivatives were synthesized. Then, to form new carbazoles, Diels-Alder reactivity of these vinylindoles was studied with various dienophiles. During the cycloaddition reaction, unusual Morita-Baylis-Hillman-type products were observed. The structure and the formation mechanism of the products is discussed. (C) 2010 Elsevier Ltd. All rights reserved.