1-(2,6-dichlorobenzyl)-3-hydroxy-3-(pyridin-2-ylmethyl)indolin-2-one | 1246646-24-1

• 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: 1-(2,6-dichlorobenzyl)-3-hydroxy-3-(pyridin-2-ylmethyl)indolin-2-one
• 英文别名: 1-[(2,6-dichlorophenyl)methyl]-3-hydroxy-3-(pyridin-2-ylmethyl)indol-2-one
• CAS: 1246646-24-1
• 化学式: C₂₁H₁₆Cl₂N₂O₂
• 分子量: 399.276
• InChiKey: VUPVLOBYLGMFGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  53.43
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(2,6-dichlorobenzyl)-3-hydroxy-3-(pyridin-2-ylmethyl)indolin-2-one 、 苯 在 三氟甲磺酸 作用下， 反应 2.0h， 以74%的产率得到1-(2,6-dichlorobenzyl)-3-phenyl-3-(pyridin-2-ylmethyl)indolin-2-one
  参考文献：
  名称：

  Preparation of aryl-substituted 2-oxyindoles by superelectrophilic chemistry

  摘要：

  A series of pyridyl-substituted 3-hydroxy-2-oxyindoles have been prepared and reacted with arenes in superacid promoted Friedel-Crafts reactions. The product aryl-substituted 2-oxyindoles are formed in generally good yields. With substituted arenes such as toluene, bromobenzene, or ethyl salicylate, the Friedel-Crafts reactions occur with excellent regioselectivity. A mechanism is proposed involving dicationic, superelectrophilic species leading to the electrophilic aromatic substitution chemistry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.011
• 作为产物：
  描述：

  碳酸甲丙酯 、 1-[(2,6-二氯苯基)甲基]吲哚-2,3-二酮 在 三氟甲磺酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-(2,6-dichlorobenzyl)-3-hydroxy-3-(pyridin-2-ylmethyl)indolin-2-one
  参考文献：
  名称：

  Preparation of aryl-substituted 2-oxyindoles by superelectrophilic chemistry

  摘要：

  A series of pyridyl-substituted 3-hydroxy-2-oxyindoles have been prepared and reacted with arenes in superacid promoted Friedel-Crafts reactions. The product aryl-substituted 2-oxyindoles are formed in generally good yields. With substituted arenes such as toluene, bromobenzene, or ethyl salicylate, the Friedel-Crafts reactions occur with excellent regioselectivity. A mechanism is proposed involving dicationic, superelectrophilic species leading to the electrophilic aromatic substitution chemistry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.011

文献信息

• Preparation of aryl-substituted 2-oxyindoles by superelectrophilic chemistry
  作者：Rajasekhar Reddy Naredla、Erum K. Raja、Douglas A. Klumpp

  DOI：10.1016/j.tetlet.2013.04.011

  日期：2013.6

  A series of pyridyl-substituted 3-hydroxy-2-oxyindoles have been prepared and reacted with arenes in superacid promoted Friedel-Crafts reactions. The product aryl-substituted 2-oxyindoles are formed in generally good yields. With substituted arenes such as toluene, bromobenzene, or ethyl salicylate, the Friedel-Crafts reactions occur with excellent regioselectivity. A mechanism is proposed involving dicationic, superelectrophilic species leading to the electrophilic aromatic substitution chemistry. (C) 2013 Elsevier Ltd. All rights reserved.