trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-methoxyquinoline | 820976-77-0

• 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: trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-methoxyquinoline
• 英文别名: trans-3-{2-[5-(4-methanesulfonyl-piperazine-1-ylmethyl)-2-nitro-phenyl]-vinyl}-2-methoxy-quinoline；2-methoxy-3-[(E)-2-[5-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-nitrophenyl]ethenyl]quinoline
• CAS: 820976-77-0
• 化学式: C₂₄H₂₆N₄O₅S
• 分子量: 482.56
• InChiKey: SRIKMCNGADKCNA-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-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， 70.0 ℃ 、103.42 kPa 条件下， 反应 14.0h， 以94%的产率得到2-methoxy-3-(5-{[4-(methylsulfonyl)-1-piperazinyl]-methyl}-1H-indol-2-yl)-quinoline
  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：

  1-[(4-硝基苯基)甲基]哌嗪 在 四丁基氟化铵 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 醋酸异丙酯 为溶剂， 反应 7.5h， 生成 trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-methoxyquinoline
  参考文献：
  名称：

  Synthesis of 5-Substituted-1H-indol-2-yl-1H-quinolin-2-ones:  A Novel Class of KDR Kinase Inhibitors

  摘要：

  A number of approaches for the synthesis of the 1H-indol-2-yl-1H-quinolin-2-one ring system found in the potent and selective KDR kinase inhibitor 1 are described. The preparation and reaction of trimethylsilylnitrobenzene 26 with 2-methoxy-3-quinolinecarboxaldehyde 28 afforded alcohol 30, which was the key intermediate for the preparation of the target compounds. Conversion of alcohol 30 to either nitroketone 36 or nitrostyrene 45 set the stage for reductive cyclization and the formation of indole 25. The quinolin-2-one functionality was unmasked in the last step to provide compound 1 in 56-60% overall yield from readily available starting materials.

  DOI：

  10.1021/jo0480545

文献信息

• Substituted indoles and a process for preparing substituted indoles
  申请人：Davies W Ian

  公开号：US20070054921A1

  公开（公告）日：2007-03-08

  The instant invention is directed to novel compounds of Formulae (I) and (II), as wells a process for preparing compounds of Formula (II). The process comprises a palladium-catalyzed reductive cyclization of a compound of Formula (I) to produce a compound of Formula (II).

  本发明涉及式（I）和（II）的新化合物，以及制备式（II）的方法。该方法包括通过钯催化的还原环化反应将式（I）的化合物还原为式（II）的化合物。
• [EN] SUBSTITUTED INDOLES AND A PROCESS FOR PREPARING SUBSTITUTED INDOLES<br/>[FR] INDOLES SUBSTITUES ET PROCEDE DE PREPARATION D'INDOLES SUBSTITUES
  申请人：MERCK & CO INC

  公开号：WO2005000804A3

  公开（公告）日：2005-08-04
• SUBSTITUTED INDOLES AND A PROCESS FOR PREPARING SUBSTITUTED INDOLES
  申请人：Merck & Co., Inc.

  公开号：EP1633694A2

  公开（公告）日：2006-03-15
• EP1633694A4
  申请人：——

  公开号：EP1633694A4

  公开（公告）日：2007-03-14
• 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.