(S)-6-(4-Dimethylaminophenyl)-4-hydroxyhex-5-en-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (S)-6-(4-Dimethylaminophenyl)-4-hydroxyhex-5-en-2-one
• 英文别名: (S)-Cynol；(E,4S)-6-[4-(dimethylamino)phenyl]-4-hydroxyhex-5-en-2-one
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: WROVZQVBUZKYAT-VIIAAUOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  rac-6-(4-Dimethylaminophenyl)-4-hydroxyhex-5-en-2-one 在 phosphate buffered saline 、 aldolase antibodies 84G₃ 作用下， 以 甲苯 为溶剂， 反应 340.0h， 生成 3-(4-dimethylamino-phenyl)-propenal 、 丙酮 、 (R)-6-(4-Dimethylaminophenyl)-4-hydroxyhex-5-en-2-one 、 (S)-6-(4-Dimethylaminophenyl)-4-hydroxyhex-5-en-2-one
  参考文献：
  名称：

  An Efficient Benchtop System for Multigram-Scale Kinetic Resolutions Using Aldolase Antibodies

  摘要：

  The preparative scale kinetic resolution of racemic aldols 1-4 using aldolase antibodies 38C2 (Aldrich no. 47995-0) and 84G3 (Aldrich no. 52785-8) is described. These reactions use a biphasic aqueous/organic solvent system that allows the catalyst to be reused. Reaction scales range from miligrams to grams, with 0.0086 to 0.12 mol% of antibody binding sites. Because antibodies 38C2 and 84G3 have opposite enantioselectivities, both aldol product enantiomers are accessible by kinetic resolution.

  DOI：

  10.1002/1521-3765(20000804)6:15<2772::aid-chem2772>3.0.co;2-j

文献信息

• ANTIBODY CATALYSIS OF ENANTIO- AND DIASTEREO-SELECTIVE ALDOL REACTIONS
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：EP1228087B1

  公开（公告）日：2010-06-09
• An Efficient Benchtop System for Multigram-Scale Kinetic Resolutions Using Aldolase Antibodies
  作者：James M. Turner、Tommy Bui、Richard A. Lerner、Carlos F. Barbas III、Benjamin List

  DOI：10.1002/1521-3765(20000804)6:15<2772::aid-chem2772>3.0.co;2-j

  日期：2000.8.4

  The preparative scale kinetic resolution of racemic aldols 1-4 using aldolase antibodies 38C2 (Aldrich no. 47995-0) and 84G3 (Aldrich no. 52785-8) is described. These reactions use a biphasic aqueous/organic solvent system that allows the catalyst to be reused. Reaction scales range from miligrams to grams, with 0.0086 to 0.12 mol% of antibody binding sites. Because antibodies 38C2 and 84G3 have opposite enantioselectivities, both aldol product enantiomers are accessible by kinetic resolution.