2-phenyl-3-ethylthio-4,4,4-trifluoromethyl-but-2-en-1-al | 149508-60-1

• 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: 2-phenyl-3-ethylthio-4,4,4-trifluoromethyl-but-2-en-1-al
• 英文别名: 3-ethylsulfanyl-4,4,4-trifluoro-2-phenylbutenal
• CAS: 149508-60-1
• 化学式: C₁₂H₁₁F₃OS
• 分子量: 260.28
• InChiKey: HBVXNGHXZXWYAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-氨基丙烷-1-磷酸 、 2-phenyl-3-ethylthio-4,4,4-trifluoromethyl-but-2-en-1-al 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.83h， 生成
  参考文献：
  名称：

  A Convenient One-Pot Synthesis of β -(Trifluoromethyl)allylaminophosphonic and Benzylaminophosphonic Acids

  摘要：

  The reductive condensation of aminoalkylphosphonic acids with beta-chloro- or beta-ethylthio-(beta-trifluoromethyl)acroleins leads to secondary (trifluoromethyl)allylaminophosphonic acids in moderate to good yields. The method appears to be useful for the preparation of benzylaminophosphonic acids.

  DOI：

  10.1080/10426500902737364
• 作为产物：
  描述：

  ethanethiolate 、 3-chloro-4,4,4-trifluoro-2-phenyl-but-2-enal 以90%的产率得到2-phenyl-3-ethylthio-4,4,4-trifluoromethyl-but-2-en-1-al
  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

• Reactivity of β-(trifluoromethyl) acroleins towards primary alkyl (or aryl) amines: synthesis of (trifluoromethyl)-1-aza-1,3-dienes and secondary (trifluoromethyl) allylamines
  作者：A. Selmi、M.M. El Gaied、G. Alvernhe

  DOI：10.1016/0022-1139(94)03166-w

  日期：1995.5

  Vilsmeier's reaction on trifluoroketones leads to β-chloro-β-(trifluoromethyl)acroleins. The addition of primary alkyl- or aryl-amines to these acroleins leads in all cases to the formation of stable (trifluoromethyl)-1-aza-1,3-dienes which can be transformed quantitatively into secondary (trifluoromethyl) allylamines by reduction with sodium borohydride.

  Vilsmeier对三氟酮的反应导致生成β-氯-β-（三氟甲基）丙烯醛。在所有情况下，向这些丙烯醛中添加伯烷基胺或芳基胺会导致形成稳定的（三氟甲基）-1-氮杂-1,3-二烯，可以通过用钠还原将其定量转化为仲（三氟甲基）烯丙基胺。硼氢化物。
• Application of Sonogashira and Baylis–Hillman Reactions with β-Trifluoromethylated Acroleins
  作者：Emna Zouaoui、Mohamed Moncef El Gaïed

  DOI：10.3184/030823409x12608085606117

  日期：2010.1

  The reaction of alkynes with 2-phenyl-3-iodo-4,4,4-trifluorobut-2-enal in the presence of palladium (0) is reported (Sonogashira reaction). Moreover, 2-(hydroxytrifluoromethylalkenyl)cyclohexenones have been prepared by the reaction of cyclohexenone and β-trifluromethylacroleins in the presence of N-methylimidazole catalysis.

  据报道，炔烃与 2-苯基-3-碘-4,4,4-三氟丁烯-2-烯醛在钯（0）存在下发生了反应（Sonogashira 反应）。此外，环己烯酮和 β-三氟甲基丙烯醛在 N-甲基咪唑催化下发生反应，制备了 2-（羟基三氟甲基烯基）环己烯酮。
• Trifluoromethyl substitution affects the regiochemistry of cyclising condensation in 1,4 substitution processes
  作者：Gérard M. Alvernhe、André J. Laurent、Isabelle M. Le Dréan、Abdelaziz Selmi

  DOI：10.1016/s0040-4039(00)60447-1

  日期：1993.4

  Beta-Trifluoromethyl beta-chloroacrolein 2 reacts with 2-mercaptoethylamine 3 to produce thiazolidine 5 instead of the expected thiazepine 8. The reason of this behaviour is the formation of the tetrahedral intermediate 6 because of stabilisation by the trifluoromethyl group ; an intramolecular substitution takes place faster than a 1,4 addition-elimination process.