2,3-diethoxy-3-(2,3-dihydro-2,3-dioxo-1H-indol-1-yl)-3H-indole | 1374156-08-7

• 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: 2,3-diethoxy-3-(2,3-dihydro-2,3-dioxo-1H-indol-1-yl)-3H-indole
• 英文别名: 1-(2,3-Diethoxyindol-3-yl)indole-2,3-dione；1-(2,3-diethoxyindol-3-yl)indole-2,3-dione
• CAS: 1374156-08-7
• 化学式: C₂₀H₁₈N₂O₄
• 分子量: 350.374
• InChiKey: NBEZDNUBXVOCNL-UHFFFAOYSA-N

物化性质

• 沸点：
  521.7±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  靛红 、 碘乙烷 在 silver carbonate 作用下， 以 苯 为溶剂， 生成 1-乙基-1H-吲哚-2,3-二酮 、 2-ethoxy-3-(2,3-dihydro-2,3-dioxo-1H-indol-1-yl)-3-hydroxy-3H-indole 、 2,3-diethoxy-3-(2,3-dihydro-2,3-dioxo-1H-indol-1-yl)-3H-indole
  参考文献：
  名称：

  Reaction of isatin with alkylating agents with acidic methylenes

  摘要：

  The reaction of isatin (1) with different alkyl halides 2 and alkaline carbonates in aprotic polar solvents leads mainly to N-alkyl derivatives 3. The use of alkylating agents that have acidic methylenes leads to competitive formation of the corresponding epoxide 5. The formation of 5 is favored by low-polarity solvents at low temperatures and strong bases. Epoxides 5c, d obtained using NaEtOH/EtOH at 0-5 degrees C are transformed into the corresponding 4-quinolinones 6 at higher temperatures. The use of Ag2CO3 allows obtaining compounds 3 as major products, along with varying amounts of labile O-alkyl derivatives 4 and dimerization products. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.010

文献信息

• Reaction of isatin with alkylating agents with acidic methylenes
  作者：María S. Shmidt、Isabel A. Perillo、Mercedes González、María M. Blanco

  DOI：10.1016/j.tetlet.2012.03.010

  日期：2012.5

  The reaction of isatin (1) with different alkyl halides 2 and alkaline carbonates in aprotic polar solvents leads mainly to N-alkyl derivatives 3. The use of alkylating agents that have acidic methylenes leads to competitive formation of the corresponding epoxide 5. The formation of 5 is favored by low-polarity solvents at low temperatures and strong bases. Epoxides 5c, d obtained using NaEtOH/EtOH at 0-5 degrees C are transformed into the corresponding 4-quinolinones 6 at higher temperatures. The use of Ag2CO3 allows obtaining compounds 3 as major products, along with varying amounts of labile O-alkyl derivatives 4 and dimerization products. (C) 2012 Elsevier Ltd. All rights reserved.