(E)-4,4,4-trifluoro-2-(p-tolylthio)but-2-en-1-ol | 1147999-87-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (E)-4,4,4-trifluoro-2-(p-tolylthio)but-2-en-1-ol
• 英文别名: (E)-4,4,4-trifluoro-2-(4-methylphenyl)sulfanylbut-2-en-1-ol
• CAS: 1147999-87-8
• 化学式: C₁₁H₁₁F₃OS
• 分子量: 248.269
• InChiKey: YWUPHAPTCOAKJJ-UXBLZVDNSA-N

物化性质

• 沸点：
  326.0±42.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-4,4,4-trifluoro-2-(p-tolylthio)but-2-en-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到(E)-(1-bromo-4,4,4-trifluorobut-2-en-2-yl)(p-tolyl)sulfane
  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
• 作为产物：
  描述：

  methyl (E)-4,4,4-trifluoro-2-(p-tolylthio)but-2-enoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以88%的产率得到(E)-4,4,4-trifluoro-2-(p-tolylthio)but-2-en-1-ol
  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.