[(1Z)-2-(ethylthio)-3,3,3-trifluoro-1-propenyl]benzene | 136000-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1Z)-2-(ethylthio)-3,3,3-trifluoro-1-propenyl]benzene
• 英文别名: (Z)-(2-Ethylsulfanyl-3,3,3-trifluoro-propenyl)-benzene；[(Z)-2-ethylsulfanyl-3,3,3-trifluoroprop-1-enyl]benzene
• CAS: 136000-20-9
• 化学式: C₁₁H₁₁F₃S
• 分子量: 232.27
• InChiKey: QQNWHVDHBXIWAY-NTMALXAHSA-N

物化性质

• 沸点：
  289.7±40.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 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：
  25.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1Z)-2-(ethylthio)-3,3,3-trifluoro-1-propenyl]benzene 在 (E)-2-cyclohexyl-1-trifluoromethylvinyl ethylsulfoxide 、 perfluoro-cis-2-n-butyl-3-n-propyloxaziridine 作用下， 以 氯仿 、 一氟三氯甲烷 为溶剂， 反应 0.5h， 生成 ((Z)-2-Ethanesulfonyl-3,3,3-trifluoro-propenyl)-benzene
  参考文献：
  名称：

  Chemoselective Synthesis of Trifluoromethylvinyl Sulfoxides and Sulfones Through Oxidation of Corresponding Sulfides

  摘要：

  在低温条件下，全氟-顺式-2,3-二烷基噁嗪类化合物 4 会将 1-三氟甲基乙烯基硫化物 1 氧化为相应的硫氧化物 2，产量可观。在室温下使用 3-氯过氧苯甲酸或相同的噁嗪类，只能生成砜 3。

  DOI：

  10.1055/s-1996-4207
• 作为产物：
  描述：

  3-chloro-4,4,4-trifluoro-2-phenyl-but-2-enal 在 氢氧化钾 作用下， 以 二氯甲烷 为溶剂， 生成 [(1Z)-2-(ethylthio)-3,3,3-trifluoro-1-propenyl]benzene
  参考文献：
  名称：

  Synthesis of trifluoromethylalkenes and alkynes. Trifluoromethyl captodative olefins

  摘要：

  beta-ethylthio-beta-trifluoromethylketones 3 and aldehydes 4 are easily prepared from beta-chloroolefines 5 and 6. Trifluoromethylalkynes 7 and captodative alkenes 8 are obtained by reaction of KOH on aldehydes 6 or 4.

  DOI：

  10.1016/0040-4039(91)80692-y

文献信息

• Z-trifluoromethyl thioenol ethers, enol ethers, and enamines; reactivity towards organolithium reagents
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Michael H. Rock

  DOI：10.1016/0040-4039(95)02118-3

  日期：1996.1

  conjugated with an unsaturation in the β-position undergo addition/elimination reactions with organolithium reagents to yield the corresponding trifluoromethyl alkenes while preserving the geometry of the double bond. Trifluoromethyl enamines exhibit a different reactivity towards organolithium reagents with a vinyl anion being formed in preference to addition/elimination products.

  与有机锂试剂进行加/消除反应的，在β位上与不饱和键合的三氟甲基烯醇醚和硫代烯醇醚，生成相应的三氟甲基烯烃，同时保留了双键的几何形状。三氟甲基烯胺对有机锂试剂表现出不同的反应性，其中乙烯基阴离子优先于加成/消除产物而形成。
• New approach to the synthesis of trifluoromethylvinyl sulfides
  作者：V. M. Muzalevskiy、A. V. Shastin、E. S. Balenkova、V. G. Nenajdenko

  DOI：10.1007/s11172-007-0236-4

  日期：2007.8

  Nucleophilic substitution reaction of halogen atom in β-chloro-and β-bromo-β-trifluoromethylstyrenes by thiolates was studied. Stereo-and regioselectivity of the reaction with respect to the electronic and sterical properties of substituents in the aromatic ring of starting styrenes was investigated. Regioisomer with geminal trifluoromethyl and alkyl-or arylthio groups was found to be formed predominantly or exclusively. The reaction proceeds stereoselectively in nearly quantitative yields. On this basis, a new convenient stereoselective method for the synthesis of trifluoromethylvinyl sulfides was elaborated.

  研究了β-氯和β-溴-β-三氟甲基苯乙烯中的卤素原子与硫醇的亲核取代反应。研究了反应的立体选择性和区域选择性与起始苯乙烯芳环上取代基的电子和立体性质的关系。发现该反应主要或只形成带有三氟甲基和烷基或芳硫基的区域异构体。该反应以接近定量的收率进行立体选择性反应。在此基础上，详细阐述了合成三氟甲基乙烯基硫化物的一种新的简便立体选择性方法。
• Short and efficient preparation of trifluoromethyl vinyl sulphides
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Abderrahim M'Bida

  DOI：10.1016/s0040-4039(00)61556-3

  日期：1993.11

  S-Alkyl trifluorothioacetate 2 reacts with stabilized and non-stabilized phosphoranes 1 to afford a new and general route to a wide range of trifluoromethyl vinyl sulphides 3. Until now, no general methods allowed the preparation of these interesting compounds.

  S-烷基trifluorothioacetate 2层发生反应以稳定的和未稳定化膦1，得到一种新的和一般途径的广泛的三氟甲基乙烯基硫化物3。迄今为止，还没有通用的方法可以制备这些有趣的化合物。
• Synthesis of Hindered and Functionalized 1-CF₃ Substituted Olefins via a Carbolithiation−Elimination−Metalation Cascade
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Denis Bouvet、Michael H. Rock

  DOI：10.1021/jo961356p

  日期：1996.1.1

  Addition of organolithium reagents to trifluoromethyl enol ethers 1a-d and thio enol ethers 2a provided stereoselectively the corresponding trisubstituted fluoroalkenes 3a-d in 70-90% yields. The products could themselves react with organolithium reagents and undergo a vinyl metalation providing, after trapping with an electrophile, tetrasubstituted olefins in excellent yields and with stereoselectivity. This method can be applied to other fluoroalkyl enol ethers (Rf = C2F5). The product, tetrasubstituted olefin, can be obtained directly from enol ether with 2 equiv of reagent through a carbolithiation-elimination-metalation cascade.
• A selective conversion of sulfide to sulfoxide in hexafluoro-2-propanol
  作者：K.S. Ravikumar、Jean-Pierre Bégué、Danièle Bonnet-Delpon

  DOI：10.1016/s0040-4039(98)00498-5

  日期：1998.5

  A facile, selective and efficient method for the oxidation of sulfides to sulfoxides by aqueous 30% H2O2 in hexafluoro-2-propanol at room temperature is described. Specific role of the solvent in the selectivity is exhibited. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.