(E)-1-(4-(3,3,3-trifluoro-1-(p-tolylthio)prop-1-enyl)phenyl)ethanone | 1147999-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-(4-(3,3,3-trifluoro-1-(p-tolylthio)prop-1-enyl)phenyl)ethanone
• 英文别名: 1-[4-[(E)-3,3,3-trifluoro-1-(4-methylphenyl)sulfanylprop-1-enyl]phenyl]ethanone
• CAS: 1147999-79-8
• 化学式: C₁₈H₁₅F₃OS
• 分子量: 336.378
• InChiKey: ZLUIWVOODHTIHQ-GZTJUZNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-碘代苯乙酮 、 (Z)-tributyl(3,3,3-trifluoro-1-(p-tolylthio)prop-1-enyl)-stannane 在 四(三苯基膦)钯 、 噻吩-2-甲酸亚铜(I) 、 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以87%的产率得到(E)-1-(4-(3,3,3-trifluoro-1-(p-tolylthio)prop-1-enyl)phenyl)ethanone
  参考文献：
  名称：

  β-Trifluoromethyl-α-functionalized-vinyl sulfides as a potential synthetic intermediate

  摘要：

  The beta-(trifluoromethyl)vinyl sulfides on treatment with n-BuLi/TMEDA at -78 degrees C were readily lithiated at an a-position of the Sulfanyl group, and the generated (beta-trifluoromethyl-alpha-sulfanylvinyl anions were reacted with a variety of electrophiles to give the corresponding beta-trifluoromethyl-alpha-functionalized-vinyl sulfides 4aa-4aq in good to excellent yields. The reactivity of some products has been examined. The palladium-catalysed cross-coupling reaction as well as homo-coupling reaction of Oaf provided the corresponding products in good yields, respectively. The Diels-Alder reaction of cyclic dienes and 14 derived from 4ao provided the desired six-membered cyclic products with high endo-trifluoromethyl group selectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.097