anti-(2RS,3SR)-3-Hydroxy-2-(4'-methoxyphenyl)-3-(2'',4'',6''-trimethylphenyl)propiononitrile

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: anti-(2RS,3SR)-3-Hydroxy-2-(4'-methoxyphenyl)-3-(2'',4'',6''-trimethylphenyl)propiononitrile
• 英文别名: (2R,3R)-3-hydroxy-2-(4-methoxyphenyl)-3-(2,4,6-trimethylphenyl)propanenitrile
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: AMGPNIGXSBQXRA-PKOBYXMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4,6-三甲基苯甲醛 、 对甲氧基苯乙腈 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 syn-(2RS,3SR)-3-Hydroxy-2-(4'-methoxyphenyl)-3-(2'',4'',6''-trimethylphenyl)propiononitrile 、 anti-(2RS,3SR)-3-Hydroxy-2-(4'-methoxyphenyl)-3-(2'',4'',6''-trimethylphenyl)propiononitrile
  参考文献：
  名称：

  Anti-Selective Aldol Reaction of Benzylic Nitriles and Synthesis of .gamma.-Amino Alcohols

  摘要：

  The stereochemistry of the aldol reaction of seven benzylic nitriles 1a-g and four aldehydes 2-5 has been studied. In all cases studied the reaction is anti-selective. Good to excellent selectivity (10:1->20:1) can be obtained if aldehydes with bulky secondary or tertiary substituents are used. The resulting aldols 6-9 are easily transformed to the corresponding gamma-amino alcohols 12-15, which may possess useful antidepressant activity.

  DOI：

  10.1021/jo00128a025

文献信息

• Anti-Selective Aldol Reaction of Benzylic Nitriles and Synthesis of .gamma.-Amino Alcohols
  作者：Paul R. Carlier、Kam Moon Lo、Michael M-C. Lo、Ian D. Williams

  DOI：10.1021/jo00128a025

  日期：1995.11

  The stereochemistry of the aldol reaction of seven benzylic nitriles 1a-g and four aldehydes 2-5 has been studied. In all cases studied the reaction is anti-selective. Good to excellent selectivity (10:1->20:1) can be obtained if aldehydes with bulky secondary or tertiary substituents are used. The resulting aldols 6-9 are easily transformed to the corresponding gamma-amino alcohols 12-15, which may possess useful antidepressant activity.