thioacetic acid S-[4-(trifluoromethyl)benzyl] ester | 873463-88-8

• 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: thioacetic acid S-[4-(trifluoromethyl)benzyl] ester
• 英文别名: S-4-(trifluoromethyl)benzyl thioacetate；S-[4-(trifluoromethyl)benzyl] ethanethioate；S-4-(trifluoromethyl)benzyl ethanethioate；S-[[4-(trifluoromethyl)phenyl]methyl] ethanethioate
• CAS: 873463-88-8
• 化学式: C₁₀H₉F₃OS
• 分子量: 234.242
• InChiKey: FZQGAAPWGZKBSM-UHFFFAOYSA-N

物化性质

• 沸点：
  258.1±40.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  thioacetic acid S-[4-(trifluoromethyl)benzyl] ester 在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 5a-[4-(trifluoromethyl)benzylsulfanyl]dihydrobicyclomycin
  参考文献：
  名称：

  Fluorine-substituted dihydrobicyclomycins: Synthesis and biochemical and biological properties

  摘要：

  Many studies show that selective introduction of fluorine within pharmacological agents leads to improved activities. In this study, we determine the effects of aryl fluorine substitution in 5a-(benzylsulfanyl)-dihydrobicyclomycin (3) on the in vitro inhibition of Escherichia coli rho-dependent ATPase activity. Compound 3 is an analog of bicyclomycin (1), which is the only known selective inhibitor of rho, and I and 3 have comparable in vitro inhibitory activities. We demonstrate that aryl fluorine substitution of 3 leads to increase in inhibitory activity but that the beneficial effects due to fluorine were dependent upon the site and number of fluorine substituents. The bioactivitics are rationalized in terms of the bond moment created by the aryl fluoride bond within the 5a-aryl dihydrobicyclomycin-rho-binding pocket. Use of this hypothesis led to file design of dihydrobicyclomycin derivatives with superior in vitro rho inhibitory activities. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.075
• 作为产物：
  描述：

  1-溴-三氟对二甲苯 、 potassium thioacetate 以 丙酮 为溶剂， 反应 18.0h， 以62%的产率得到thioacetic acid S-[4-(trifluoromethyl)benzyl] ester
  参考文献：
  名称：

  钯催化的硫代乙酸苄酯和卤代芳烃的交叉偶联

  摘要：

  已经开发并优化了利用苄基硫代乙酸酯的原位脱保护作为游离硫醇的替代物来制备苄基芳基硫醚的方法。获得具有良好的空气稳定性，无异味且易于制备的硫代酯的各种苄基芳基硫醚，具有良好或优异的收率。还已经证明了一种由一锅的卤化物，一硫代乙酸钾和一芳基溴形成苄基芳基硫醚的一锅法方案。

  DOI：

  10.1021/ol201564j

文献信息

• New Protocol for the Synthesis of S‐Thioesters from Benzylic, Allylic and Tertiary Alcohols with Thioacetic Acid
  作者：Abdelhak Lachguar、Uchchhal Bandyopadhyay、Mehdi Ech‐Chariy、Sandrine Vincendeau、Catherine Audin、Jean‐Claude Daran、Eric Manoury、Rinaldo Poli、Eric Deydier

  DOI：10.1002/chem.202302551

  日期：2024.1.2

  Reaction of activated alcohols with neat thioacetic acid catalyzed by HBF4 provides a convenient entry into thioacetates, protected version of the corresponding thiols; the generation of intermediate acetates and thionoacetates and the mechanism of their further conversion to the final products has been fully rationalized.

  活化醇与纯硫代乙酸在 HBF 4催化下发生反应，可以方便地生成硫代乙酸酯，即相应硫醇的受保护形式；中间体乙酸酯和硫代乙酸酯的生成及其进一步转化为最终产品的机制已完全合理化。
• Fluorine-substituted dihydrobicyclomycins: Synthesis and biochemical and biological properties
  作者：Boon-Saeng Park、William Widger、Harold Kohn

  DOI：10.1016/j.bmc.2005.07.075

  日期：2006.1

  Many studies show that selective introduction of fluorine within pharmacological agents leads to improved activities. In this study, we determine the effects of aryl fluorine substitution in 5a-(benzylsulfanyl)-dihydrobicyclomycin (3) on the in vitro inhibition of Escherichia coli rho-dependent ATPase activity. Compound 3 is an analog of bicyclomycin (1), which is the only known selective inhibitor of rho, and I and 3 have comparable in vitro inhibitory activities. We demonstrate that aryl fluorine substitution of 3 leads to increase in inhibitory activity but that the beneficial effects due to fluorine were dependent upon the site and number of fluorine substituents. The bioactivitics are rationalized in terms of the bond moment created by the aryl fluoride bond within the 5a-aryl dihydrobicyclomycin-rho-binding pocket. Use of this hypothesis led to file design of dihydrobicyclomycin derivatives with superior in vitro rho inhibitory activities. (c) 2005 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Cross-Coupling of Benzyl Thioacetates and Aryl Halides
  作者：Krista M. Wager、Matthew H. Daniels

  DOI：10.1021/ol201564j

  日期：2011.8.5

  for preparing benzyl aryl thioethers utilizing an in situ deprotection of benzyl thioacetates as an alternative to free thiols as starting materials has been developed and optimized. Good to excellent yields of diverse benzyl aryl thioethers are obtained with air-stable, odor-free, and easy to prepare thioesters. A one-pot protocol for forming benzyl aryl thioethers from a benzyl halide, potassium thioacetate

  已经开发并优化了利用苄基硫代乙酸酯的原位脱保护作为游离硫醇的替代物来制备苄基芳基硫醚的方法。获得具有良好的空气稳定性，无异味且易于制备的硫代酯的各种苄基芳基硫醚，具有良好或优异的收率。还已经证明了一种由一锅的卤化物，一硫代乙酸钾和一芳基溴形成苄基芳基硫醚的一锅法方案。