4-(3,4,5-trimethoxyphenyl)indoline-2,3-dione | 861389-62-0

• 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: 4-(3,4,5-trimethoxyphenyl)indoline-2,3-dione
• 英文别名: 4-(3,4,5-trimethoxyphenyl)isatin
• CAS: 861389-62-0
• 化学式: C₁₇H₁₅NO₅
• 分子量: 313.31
• InChiKey: WQLJNEMKAZXPAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(3,4,5-trimethoxyphenyl)indoline-2,3-dione 在 sodium hydroxide 、 双氧水 作用下， 反应 0.5h， 以14%的产率得到6-(3,4,5-trimethoxyphenyl)anthranilic acid
  参考文献：
  名称：

  Direct synthesis of new arylanthranilic acids via a Suzuki cross-coupling reaction from iodoisatins

  摘要：

  Direct synthesis of new arylanthranilic acids via a Suzuki cross-coupling reaction with iodoisatins as key intermediates is described. A 'one pot' procedure is proposed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.022
• 作为产物：
  描述：

  3-iodo-isonitrosoacetanilide 在 四(三苯基膦)钯 、 硫酸 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 为溶剂， 生成 4-(3,4,5-trimethoxyphenyl)indoline-2,3-dione
  参考文献：
  名称：

  Direct synthesis of new arylanthranilic acids via a Suzuki cross-coupling reaction from iodoisatins

  摘要：

  Direct synthesis of new arylanthranilic acids via a Suzuki cross-coupling reaction with iodoisatins as key intermediates is described. A 'one pot' procedure is proposed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.022

文献信息

• Efficient synthesis of bulky 4-substituted-isatins via microwave-promoted Suzuki cross-coupling reaction
  作者：Yu-Chao Liu、Chen-Jin Ye、Qiong Chen、Guang-Fu Yang

  DOI：10.1016/j.tetlet.2012.12.021

  日期：2013.2

  Indoline-2,3-diones (isatins) and their derivatives are important heterocycles found in nature and present in numerous bioactive compounds. Very few examples related to the synthesis of 4-substituted-arylisatins have been reported before. Utilizing microwave irradiation, the synthesis of bulky 4-substituted-arylisatins via a Suzuki cross-coupling has been developed with a wide range of substrates. All the reactions proceeded smoothly and afforded moderate to excellent yields of products, which indicating that electronic effects and steric modifications have little effect on this reaction. (C) 2012 Elsevier Ltd. All rights reserved.