3-[(E)-2-(5-chloro-2-nitrophenyl)vinyl]-2-methoxyquinoline | 861631-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-[(E)-2-(5-chloro-2-nitrophenyl)vinyl]-2-methoxyquinoline
• 英文别名: 3-[(E)-2-(5-chloro-2-nitrophenyl)ethenyl]-2-methoxyquinoline
• CAS: 861631-62-1
• 化学式: C₁₈H₁₃ClN₂O₃
• 分子量: 340.766
• InChiKey: QFRUBQGWQYGZTK-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(E)-2-(5-chloro-2-nitrophenyl)vinyl]-2-methoxyquinoline 在 palladium diacetate 1,10-菲罗啉 、 一氧化碳 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、103.42 kPa 条件下， 反应 16.0h， 以91%的产率得到3-(5-chloro-1H-indol-2-yl)-2-methoxyquinoline
  参考文献：
  名称：

  A highly active catalyst for the reductive cyclization of ortho-nitrostyrenes under mild conditions

  摘要：

  A mild and efficient method for the palladium-Catalyzed reductive Cyclization of ortho-nitrostyrenes to afford indoles is reported. \Treatment of ortho-nitrostyrenes with 0.1 mol% palladium (II) trifluoracetate [Pd(TFA)(2)] and 0.7 mol% 3.4,7,8-tetramethyl-1,10-phenanthroline (tm-phen) in DMF at 15 psig CO and 80 degrees C afforded indoles in good to excellent yields. When the reaction was conducted in toluene. the corresponding N-hydroxyindole was isolated. A mechanism that accounts for the formation of N-hydroxyindole is proposed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.142
• 作为产物：
  描述：

  2-甲氧基喹啉-3-甲醛 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸酐 作用下， 以 醋酸异丙酯 、 二甲基亚砜 为溶剂， 反应 17.0h， 生成 3-[(E)-2-(5-chloro-2-nitrophenyl)vinyl]-2-methoxyquinoline
  参考文献：
  名称：

  A highly active catalyst for the reductive cyclization of ortho-nitrostyrenes under mild conditions

  摘要：

  A mild and efficient method for the palladium-Catalyzed reductive Cyclization of ortho-nitrostyrenes to afford indoles is reported. \Treatment of ortho-nitrostyrenes with 0.1 mol% palladium (II) trifluoracetate [Pd(TFA)(2)] and 0.7 mol% 3.4,7,8-tetramethyl-1,10-phenanthroline (tm-phen) in DMF at 15 psig CO and 80 degrees C afforded indoles in good to excellent yields. When the reaction was conducted in toluene. the corresponding N-hydroxyindole was isolated. A mechanism that accounts for the formation of N-hydroxyindole is proposed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.142

文献信息

• A highly active catalyst for the reductive cyclization of ortho-nitrostyrenes under mild conditions
  作者：Ian W. Davies、Jacqueline H. Smitrovich、Rick Sidler、Chuanxing Qu、Venita Gresham、Charles Bazaral

  DOI：10.1016/j.tet.2005.03.142

  日期：2005.6

  A mild and efficient method for the palladium-Catalyzed reductive Cyclization of ortho-nitrostyrenes to afford indoles is reported. \Treatment of ortho-nitrostyrenes with 0.1 mol% palladium (II) trifluoracetate [Pd(TFA)(2)] and 0.7 mol% 3.4,7,8-tetramethyl-1,10-phenanthroline (tm-phen) in DMF at 15 psig CO and 80 degrees C afforded indoles in good to excellent yields. When the reaction was conducted in toluene. the corresponding N-hydroxyindole was isolated. A mechanism that accounts for the formation of N-hydroxyindole is proposed. (c) 2005 Elsevier Ltd. All rights reserved.