4-(3,3,3-trifluoro-1-(p-tolylthio)prop-1-enylthio)-1-methylbenzene | 1147999-69-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(3,3,3-trifluoro-1-(p-tolylthio)prop-1-enylthio)-1-methylbenzene
• CAS: 1147999-69-6
• 化学式: C₁₇H₁₅F₃S₂
• 分子量: 340.433
• InChiKey: YMEUKJYUNYMYHH-UHFFFAOYSA-N

物化性质

• 熔点：
  57.5-59.0 °C
• 沸点：
  442.8±45.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (E)-1-(4-tolylthio)-3,3,3-trifluoroprop-1-ene 、 4-甲基苯硫代磺酸 S-(4-甲基苯基)酯 在 四甲基乙二胺 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.42h， 以58%的产率得到4-(3,3,3-trifluoro-1-(p-tolylthio)prop-1-enylthio)-1-methylbenzene
  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

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.