2,2,2-trifluoro-N-((2RS,3SR)-2-(3-methoxyphenyl)-1-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinolin-3-yl)acetamide

• 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: 2,2,2-trifluoro-N-((2RS,3SR)-2-(3-methoxyphenyl)-1-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinolin-3-yl)acetamide
• 英文别名: 2,2,2-trifluoro-N-[(2R,3S)-2-(3-methoxyphenyl)-1-(4-methoxyphenyl)-3,4-dihydro-2H-quinolin-3-yl]acetamide
• 化学式: C₂₅H₂₃F₃N₂O₃
• 分子量: 456.464
• InChiKey: BJCYYDTUYFKPSA-JTHBVZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(3-methoxyphenyl)-N-(4-methoxyphenyl)methanimine 在 盐酸 、 四(三苯基膦)钯 、 三乙基硼氢化锂 、 potassium carbonate 、 N,N-二异丙基乙胺 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 19.83h， 生成 2,2,2-trifluoro-N-((2RS,3SR)-2-(3-methoxyphenyl)-1-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinolin-3-yl)acetamide
  参考文献：
  名称：

  Reductive Nitro-Mannich Route for the Synthesis of 1,2-Diamine Containing Indolines and Tetrahydroquinolines

  摘要：

  A one-pot, 1,4-hydride addition nitro-Mannich reaction between a set of nitroalkenes 3 and a wide range of N-p-methoxyphenyl-protected aldimines, derived from alkyl, aryl and heteroaryl aldehydes, followed by Zn/HCl reduction leads to stereochemically defined 1,2-diamines. These underwent palladium-catalyzed cyclization and depending upon the presence or not of the trifluoroacetamide protecting group gave either tetrahydroquinolines 18 or indolines 14 in high overall yield and diastereoselectivity (19 examples each). In each case, the more nucleophilic pendant amine cyclizes to give a benzofused saturated heterocyclic 5- or 6-membered ring, with an additional vicinal amino stereocenter in each.

  DOI：

  10.1021/jo3010827

文献信息

• Reductive Nitro-Mannich Route for the Synthesis of 1,2-Diamine Containing Indolines and Tetrahydroquinolines
  作者：James C. Anderson、Adam Noble、Derek A. Tocher

  DOI：10.1021/jo3010827

  日期：2012.8.17

  A one-pot, 1,4-hydride addition nitro-Mannich reaction between a set of nitroalkenes 3 and a wide range of N-p-methoxyphenyl-protected aldimines, derived from alkyl, aryl and heteroaryl aldehydes, followed by Zn/HCl reduction leads to stereochemically defined 1,2-diamines. These underwent palladium-catalyzed cyclization and depending upon the presence or not of the trifluoroacetamide protecting group gave either tetrahydroquinolines 18 or indolines 14 in high overall yield and diastereoselectivity (19 examples each). In each case, the more nucleophilic pendant amine cyclizes to give a benzofused saturated heterocyclic 5- or 6-membered ring, with an additional vicinal amino stereocenter in each.