(4R,6S)-2-(4-fluorophenyl)-6-hydroxy-4-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile | 1280199-31-6

• 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: (4R,6S)-2-(4-fluorophenyl)-6-hydroxy-4-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile
• 英文别名: (2S,4R)-6-(4-fluorophenyl)-2-hydroxy-4-phenyl-2-(trichloromethyl)-3,4-dihydropyran-5-carbonitrile
• CAS: 1280199-31-6
• 化学式: C₁₉H₁₃Cl₃FNO₂
• 分子量: 412.675
• InChiKey: XTJRMLHBPSJYLC-QAPCUYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 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：
  4

反应信息

• 作为产物：
  描述：

  4-氟苯甲酰基乙腈 、 1,1,1-Trichloro-4-phenylbut-3-en-2-one 在 (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 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 96.0h， 生成 (4R,6S)-2-(4-fluorophenyl)-6-hydroxy-4-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile 、 (4S,6R)-2-(4-fluorophenyl)-6-hydroxy-4-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.