ethyl (E)-4,4,4-trifluoro-2-(p-tolylthio)but-2-enoate

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl (E)-4,4,4-trifluoro-2-(p-tolylthio)but-2-enoate
• 英文别名: ethyl (E)-4,4,4-trifluoro-2-(4-methylphenyl)sulfanylbut-2-enoate
• 化学式: C₁₃H₁₃F₃O₂S
• 分子量: 290.306
• InChiKey: HXSAWVCIQWCAHN-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲苯硫酚 在 氢氧化钾 、 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 0.25h， 生成 ethyl (E)-4,4,4-trifluoro-2-(p-tolylthio)but-2-enoate
  参考文献：
  名称：

  Facile synthesis of α-functionalized vinyl sulfides bearing β-trifluoromethyl group: a highly potential CF3-containing building blocks

  摘要：

  The beta-(trifluoromethyl)vinylsulfides on treatment with n-BuLi/TMEDA were readily lithiated at a-position of the sulfanyl group, and the generated alpha-lithiovinylsulfides were trapped with a variety of electrophiles to give the corresponding beta-trifluoromethyl-alpha-functionalized vinylsulfides in good to high yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.105

文献信息

• β-Trifluoromethyl-α-functionalized-vinyl sulfides as a potential synthetic intermediate
  作者：Takeshi Hanamoto、Ryoko Anno、Kenji Yamada、Kousuke Ryu、Ryoko Maeda、Kazuya Aoi、Hiroshi Furuno

  DOI：10.1016/j.tet.2009.01.097

  日期：2009.4

  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.
• Facile synthesis of α-functionalized vinyl sulfides bearing β-trifluoromethyl group: a highly potential CF3-containing building blocks
  作者：Takeshi Hanamoto、Ryoko Anno、Kenji Yamada、Kousuke Ryu

  DOI：10.1016/j.tetlet.2007.03.105

  日期：2007.5

  The beta-(trifluoromethyl)vinylsulfides on treatment with n-BuLi/TMEDA were readily lithiated at a-position of the sulfanyl group, and the generated alpha-lithiovinylsulfides were trapped with a variety of electrophiles to give the corresponding beta-trifluoromethyl-alpha-functionalized vinylsulfides in good to high yields. (c) 2007 Elsevier Ltd. All rights reserved.