(3R,4S)-2-(trimethylsilyl)ethyl 4-(((2R,3R)-3-(2-bromo-6-methoxyquinolin-4-yl)oxiran-2-yl)methyl)-3-vinylpiperidine-1-carboxylate | 1246028-61-4

• 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: (3R,4S)-2-(trimethylsilyl)ethyl 4-(((2R,3R)-3-(2-bromo-6-methoxyquinolin-4-yl)oxiran-2-yl)methyl)-3-vinylpiperidine-1-carboxylate
• 英文别名: 2-trimethylsilylethyl (3R,4S)-4-[[(2R,3R)-3-(2-bromo-6-methoxyquinolin-4-yl)oxiran-2-yl]methyl]-3-ethenylpiperidine-1-carboxylate
• CAS: 1246028-61-4
• 化学式: C₂₆H₃₅BrN₂O₄Si
• 分子量: 547.564
• InChiKey: SUSOERKQJLWEPI-WBEAWWQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl (3R,4S)-4-(2-oxoethyl)-3-vinylpiperidine-1-carboxylate 、 (1S,3S,4R)-2-((2-bromo-6-methoxyquinolin-4-yl)methyl)-3-((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)-2-thioniabicyclo[2.2.1]heptane tetrafluoroborate 在 potassium hydroxide 作用下， 以 乙腈 、 叔丁醇 为溶剂， 反应 48.0h， 生成 (3R,4S)-2-(trimethylsilyl)ethyl 4-(((2S,3S)-3-(2-bromo-6-methoxyquinolin-4-yl)oxiran-2-yl)methyl)-3-vinylpiperidine-1-carboxylate 、 (3R,4S)-2-(trimethylsilyl)ethyl 4-(((2R,3R)-3-(2-bromo-6-methoxyquinolin-4-yl)oxiran-2-yl)methyl)-3-vinylpiperidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of quinine and quinidine using sulfur ylide-mediated asymmetric epoxidation as a key step

  摘要：

  The epoxidation of meroquinene aldehyde with a chiral sulfur ylide as the key step in the synthesis of quinine and quinidine is described. The epoxidation reactions proceed under reagent control with high selectivity and good yield. The effect of sulfide and ylide substituents on the stereochemical outcome of the reaction is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.046

文献信息

• Synthesis of quinine and quinidine using sulfur ylide-mediated asymmetric epoxidation as a key step
  作者：Muhammad Arshad、M. Alejandro Fernández、Eoghan M. McGarrigle、Varinder K. Aggarwal

  DOI：10.1016/j.tetasy.2010.04.046

  日期：2010.7

  The epoxidation of meroquinene aldehyde with a chiral sulfur ylide as the key step in the synthesis of quinine and quinidine is described. The epoxidation reactions proceed under reagent control with high selectivity and good yield. The effect of sulfide and ylide substituents on the stereochemical outcome of the reaction is discussed. (C) 2010 Elsevier Ltd. All rights reserved.