(E)-1,1,1-trichloro-4-(2,4-dichlorophenyl)but-3-en-2-one | 1280199-16-7

• 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: (E)-1,1,1-trichloro-4-(2,4-dichlorophenyl)but-3-en-2-one
• CAS: 1280199-16-7
• 化学式: C₁₀H₅Cl₅O
• 分子量: 318.414
• InChiKey: ZSCUBDDBHLSDAA-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-1,1,1-trichloro-4-(2,4-dichlorophenyl)but-3-en-2-one 、 苯甲酰乙腈 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 36.0h， 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
• 作为产物：
  描述：

  (E)-3-(2,4-dichlorophenyl)acrylaldehyde 在 manganese(IV) oxide 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (E)-1,1,1-trichloro-4-(2,4-dichlorophenyl)but-3-en-2-one
  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.