(2S,4S)-2-hydroxy-6-phenyl-4-thiophen-2-yl-2-(trifluoromethyl)-3,4-dihydropyran-5-carbonitrile

• 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: (2S,4S)-2-hydroxy-6-phenyl-4-thiophen-2-yl-2-(trifluoromethyl)-3,4-dihydropyran-5-carbonitrile
• 化学式: C₁₇H₁₂F₃NO₂S
• 分子量: 351.349
• InChiKey: XXCBDYZBAVMTHU-LRDDRELGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  81.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,4S)-2-hydroxy-6-phenyl-4-thiophen-2-yl-2-(trifluoromethyl)-3,4-dihydropyran-5-carbonitrile 在 乙酸铵 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 2-phenyl-4-(2-thienyl)-6-(trifluoromethyl)-1,4-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  Efficient route to 6-CF3-substituted nicotinic acid derivatives

  摘要：

  A novel synthetic sequence for preparation of CF3-pyridines is presented. Reaction of alpha,beta-unsaturated trifluoromethylketones with alpha-cyanoketones leads to alpha-hydroxydihydropyranes I containing CF3-group. alpha-Hydroxydihydropyranes can be easily transformed to alpha-hydroxytetrahydropyridines, 1,4-dihydropyridines and CF3-pyridines. All CF3-pyridine derivatives were obtained in good yields. This route can be applied for preparation of CF3-pyridines containing various substituents with further possible modification on cyano-group. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2006.03.007
• 作为产物：
  描述：

  苯甲酰乙腈 、 (E)-1,1,1-trifluoro-4-(thiophen-2-yl)but-3-en-2-one 在 potassium fluoride 作用下， 以 异丙醇 为溶剂， 以80%的产率得到(2S,4S)-2-hydroxy-6-phenyl-4-thiophen-2-yl-2-(trifluoromethyl)-3,4-dihydropyran-5-carbonitrile
  参考文献：
  名称：

  Diastereoselective synthesis of α-hydroxydihydropyrans containing the CF3 group

  摘要：

  A new method for the stereoselective synthesis of 2-trifluoromethyl-2-hydroxy-4,6-diaryl-5-cyano-2,3-dihydropyrans using reactions of alpha,beta-unsaturated trifluoromethyl ketones with substituted alpha-cyanoacetophenones is proposed.

  DOI：

  10.1070/mc2006v016n03abeh002283

文献信息

• Highly enantio- and diastereoselective synthesis of α-trifluoromethyldihydropyrans using a novel bifunctional piperazine-thiourea catalyst
  作者：Peng Li、Zhuo Chai、Sheng-Li Zhao、Ying-Quan Yang、Hai-Feng Wang、Chang-Wu Zheng、Yue-Peng Cai、Gang Zhao、Shi-Zheng Zhu

  DOI：10.1039/b915210e

  日期：——

  The first enantioselective Michael addition of alpha-cyanoketones to alpha,beta-unsaturated trifluoromethyl ketones using a novel piperazine-thiourea catalyst was described. The resulting alpha-trifluoromethyldihydropyrans were obtained in high yields and with up to 95% ee within a short reaction time. A useful transformation of the chiral adduct was also illustrated.

  描述了使用新型哌嗪-硫脲催化剂将α-氰基酮向α，β-不饱和三氟甲基酮的第一对映选择性迈克尔加成。在短时间内，以高收率和高达95％ee获得了所得的α-三氟甲基二氢吡喃。还说明了手性加合物的有用转化。
• Diastereoselective synthesis of α-hydroxydihydropyrans containing the CF3 group
  作者：Valentine G. Nenajdenko、Sergey V. Druzhinin、Elizabeth S. Balenkova

  DOI：10.1070/mc2006v016n03abeh002283

  日期：2006.1

  A new method for the stereoselective synthesis of 2-trifluoromethyl-2-hydroxy-4,6-diaryl-5-cyano-2,3-dihydropyrans using reactions of alpha,beta-unsaturated trifluoromethyl ketones with substituted alpha-cyanoacetophenones is proposed.
• Efficient route to 6-CF3-substituted nicotinic acid derivatives
  作者：Valentine G. Nenajdenko、Sergey V. Druzhinin、Elizabeth S. Balenkova

  DOI：10.1016/j.jfluchem.2006.03.007

  日期：2006.7

  A novel synthetic sequence for preparation of CF3-pyridines is presented. Reaction of alpha,beta-unsaturated trifluoromethylketones with alpha-cyanoketones leads to alpha-hydroxydihydropyranes I containing CF3-group. alpha-Hydroxydihydropyranes can be easily transformed to alpha-hydroxytetrahydropyridines, 1,4-dihydropyridines and CF3-pyridines. All CF3-pyridine derivatives were obtained in good yields. This route can be applied for preparation of CF3-pyridines containing various substituents with further possible modification on cyano-group. (c) 2006 Elsevier B.V. All rights reserved.