(S)-3-(4-cyano-3-(trifluoromethyl)phenyl)-1-(1-phenylethyl)-2-thioxotetrahydropyrimidin-4(1H)-one | 1380413-08-0

• 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: (S)-3-(4-cyano-3-(trifluoromethyl)phenyl)-1-(1-phenylethyl)-2-thioxotetrahydropyrimidin-4(1H)-one
• 英文别名: 4-[6-oxo-3-[(1S)-1-phenylethyl]-2-sulfanylidene-1,3-diazinan-1-yl]-2-(trifluoromethyl)benzonitrile
• CAS: 1380413-08-0
• 化学式: C₂₀H₁₆F₃N₃OS
• 分子量: 403.428
• InChiKey: IKDFCXZMFQAUQO-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-cyano-3-(trifluoromethyl)phenyl)-1-(1-phenylethyl)-2-thioxotetrahydropyrimidin-4(1H)-one 、 4-氯苄溴 在 lithium hexamethyldisilazane 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以14%的产率得到(S)-3-(4-cyano-3-(trifluoromethyl)phenyl)-5-(4-chlorobenzyl)-1-((S)-1-phenylethyl)-2-thioxotetrahydropyrimidin-4(1H)-one
  参考文献：
  名称：

  Additive controlled, stereoselective benzylation of 2-thioxotetrahydropyrimidin-4(1H)-ones via chiral induction from a remote stereocenter

  摘要：

  Stereoselective alkylation reactions of 3-aryl-1-alkyl-2-thioxotetrahydropyrimidin-4(1H)-one derivatives were studied. The reaction conditions were optimized to obtain the monobenzylated adduct with improved diastereoselectivity by regulating the reaction kinetics using HMPA as the additive and chiral ethyl lactate as the quencher. The absolute configuration of the product was established by NMR experiments, computational calculations, and single crystal X-ray analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.04.002
• 作为产物：
  描述：

  (αS)-methyl N-α-methylbenzyl-3-aminopropanoate 、 4-异硫代氰酰基-2-(三氟甲基)苯甲腈 在 lithium perchlorate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.2h， 以85%的产率得到(S)-3-(4-cyano-3-(trifluoromethyl)phenyl)-1-(1-phenylethyl)-2-thioxotetrahydropyrimidin-4(1H)-one
  参考文献：
  名称：

  Additive controlled, stereoselective benzylation of 2-thioxotetrahydropyrimidin-4(1H)-ones via chiral induction from a remote stereocenter

  摘要：

  Stereoselective alkylation reactions of 3-aryl-1-alkyl-2-thioxotetrahydropyrimidin-4(1H)-one derivatives were studied. The reaction conditions were optimized to obtain the monobenzylated adduct with improved diastereoselectivity by regulating the reaction kinetics using HMPA as the additive and chiral ethyl lactate as the quencher. The absolute configuration of the product was established by NMR experiments, computational calculations, and single crystal X-ray analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.04.002