(E)-1-(4-tolylthio)-3,3,3-trifluoroprop-1-ene | 940881-02-7

• 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)-1-(4-tolylthio)-3,3,3-trifluoroprop-1-ene
• 英文别名: [(3,3,3-Trifluoro-1-propen-1-yl)thio]toluene；1-methyl-4-[(E)-3,3,3-trifluoroprop-1-enyl]sulfanylbenzene
• CAS: 940881-02-7
• 化学式: C₁₀H₉F₃S
• 分子量: 218.243
• InChiKey: XUOIOTQFOOCXAQ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-tolylthio)-3,3,3-trifluoroprop-1-ene 在 正丁基锂 、 四甲基乙二胺 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以91%的产率得到(Z)-(3,3,3-trifluoro-1-iodoprop-1-enyl)(p-tolyl)sulfane
  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
• 作为产物：
  描述：

  (Z)-1-(p-tolylthio)-3,3,3-trifluoroprop-1-en-2-yl trifluoromethanesulfonate 在 三乙基硅烷 、 palladium diacetate 、 三苯基膦 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以95%的产率得到(E)-1-(4-tolylthio)-3,3,3-trifluoroprop-1-ene
  参考文献：
  名称：

  钯催化的（Z）-三氟甲基链烯基三氟甲磺酸酯的几何选择性加氢：（Z）或（E）-3,3,3-三氟丙烯基衍生物的有效方法

  摘要：

  描述了钯催化的（Z）-三氟甲基链烯基三氟甲磺酸酯的加氢反应，可提供（Z）-或（E）-3,3,3-三氟丙烯基衍生物，且具有良好的发散几何控制，且收率高。在Pd（OAc）2 / PPh 3的催化下，用HSiEt 3还原（Z）-三氟甲基链烯基三氟甲磺酸酯，得到（E）-3,3,3-三氟丙烯基衍生物，同时使用HCOOH / Et 3 N作为还原剂，（Z）-异构体是通过消除/氢化串联途径获得的。两种转化均显示出优异的几何选择性。

  DOI：

  10.1039/c7ob00970d

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.
• [EN] COMPOUNDS INCLUDING PIMELIC ACID DERIVATIVES AS HDAC INHIBITORS<br/>[FR] COMPOSÉS COMPRENANT DES DÉRIVÉS D'ACIDE PIMÉLIQUE EN TANT QU'INHIBITEURS DE HDAC
  申请人：REPLIGEN CORP

  公开号：WO2010028193A1

  公开（公告）日：2010-03-11

  HDAC inhibitors of Formulas I, II, and III are provided. Also provided are methods of treating a neurological conditions by administering the compounds and the use of the compounds as medicaments.
• 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.
• Palladium-catalyzed geometrically selective hydrogenation of (Z)-trifluoromethyl alkenyl triflate: an efficient approach to (Z) or (E)-3,3,3-trifluoropropenyl derivatives
  作者：Yilong Zhao、Yuhan Zhou、Chunxia Zhang、Huan Wang、Jinfeng Zhao、Kun Jin、Jihong Liu、Jianhui Liu、Jingping Qu

  DOI：10.1039/c7ob00970d

  日期：——

  hydrogenation of (Z)-trifluoromethyl alkenyl triflate providing either (Z)- or (E)-3,3,3-trifluoropropenyl derivatives with excellent divergent geometric control in good yield is described. Catalyzed by Pd(OAc)2/PPh3, the reduction of (Z)-trifluoromethyl alkenyl triflates with HSiEt3 gave (E)-3,3,3-trifluoropropenyl derivatives, and while using HCOOH/Et3N as the reducing agent, the (Z)-isomers were obtained

  描述了钯催化的（Z）-三氟甲基链烯基三氟甲磺酸酯的加氢反应，可提供（Z）-或（E）-3,3,3-三氟丙烯基衍生物，且具有良好的发散几何控制，且收率高。在Pd（OAc）2 / PPh 3的催化下，用HSiEt 3还原（Z）-三氟甲基链烯基三氟甲磺酸酯，得到（E）-3,3,3-三氟丙烯基衍生物，同时使用HCOOH / Et 3 N作为还原剂，（Z）-异构体是通过消除/氢化串联途径获得的。两种转化均显示出优异的几何选择性。