methyl 3-[2-hydroxy-2-(2-methoxyquinolin-3-yl)ethyl]-4-nitrobenzoate | 851777-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-[2-hydroxy-2-(2-methoxyquinolin-3-yl)ethyl]-4-nitrobenzoate
• CAS: 851777-21-4
• 化学式: C₂₀H₁₈N₂O₆
• 分子量: 382.373
• InChiKey: RPPOSPUZPUEPMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-[2-hydroxy-2-(2-methoxyquinolin-3-yl)ethyl]-4-nitrobenzoate 在 palladium(II) trifluoroacetate 3,4,7,8-四甲基-1,10-菲罗啉 、 一氧化碳 、 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 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、103.42 kPa 条件下， 反应 30.0h， 生成 methyl 2-(2-methoxyquinolin-3-yl)-1H-indole-5-carboxylate
  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：

  3-甲基-4-硝基苯甲酸甲酯 、 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 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以80%的产率得到methyl 3-[2-hydroxy-2-(2-methoxyquinolin-3-yl)ethyl]-4-nitrobenzoate
  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 Rapid Synthesis of 2-Aryl-5-substituted-2,3-dihydrobenzofurans
  作者：Jeffrey T. Kuethe、Audrey Wong、Michel Journet、Ian W. Davies

  DOI：10.1021/jo0500941

  日期：2005.4.1

  An effective strategy has been developed for the rapid and efficient one-pot synthesis of 2-aryl-5-substituted-2,3-dihydrobenzofurans from readily available o-nitrotoluenes and aromatic aldehydes. This strategy allows access to a structurally diverse array of products for further manipulation.
• 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.