(4S,6S)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile | 1280199-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,6S)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile
• 英文别名: (2S,4S)-4-(2,4-dichlorophenyl)-2-hydroxy-6-phenyl-2-(trichloromethyl)-3,4-dihydropyran-5-carbonitrile
• CAS: 1280199-27-0
• 化学式: C₁₉H₁₂Cl₅NO₂
• 分子量: 463.575
• InChiKey: OUBJCZNDDREWDO-KDOFPFPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (E)-3-(2,4-dichlorophenyl)acrylaldehyde 在 manganese(IV) oxide 、 (S)-1-(1-(4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl)-3-phenylpropan-2-yl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea 、 potassium hydroxide 作用下， 以 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 (4R,6R)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile 、 (4S,6S)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile
  参考文献：
  名称：

  Highly enantioselective synthesis of α-trichloromethyldihydropyrans catalyzed by bifunctional organocatalysts

  摘要：

  The enantioselective Michael addition of alpha-cyanoketones to alpha,beta-unsaturated trichloromethyl ketones was firstly reported. With a phenylalanine-derived bifunctional piperazine/thiourea catalyst, a series of alpha-trichloromethyldihydropyrans were obtained with up to 95% ee and 99% yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.043

文献信息

• Highly enantioselective synthesis of α-trichloromethyldihydropyrans catalyzed by bifunctional organocatalysts
  作者：Hai-Feng Wang、Peng Li、Hai-Feng Cui、Xiao-Wei Wang、Jun-Kang Zhang、Wen Liu、Gang Zhao

  DOI：10.1016/j.tet.2011.01.043

  日期：2011.3

  The enantioselective Michael addition of alpha-cyanoketones to alpha,beta-unsaturated trichloromethyl ketones was firstly reported. With a phenylalanine-derived bifunctional piperazine/thiourea catalyst, a series of alpha-trichloromethyldihydropyrans were obtained with up to 95% ee and 99% yield. (C) 2011 Elsevier Ltd. All rights reserved.