1,1,1-trifluoro-3-phenyl-3-phenylthio-2-propanone | 177747-66-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,1,1-trifluoro-3-phenyl-3-phenylthio-2-propanone
• 英文别名: 1,1,1-Trifluoro-3-phenyl-3-phenylsulfanylpropan-2-one
• CAS: 177747-66-9
• 化学式: C₁₅H₁₁F₃OS
• 分子量: 296.313
• InChiKey: NMDGLIVXMPYRTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  1,1,1-trifluoro-3-phenyl-3-phenylthio-2-propanone 在 Candida lipolytica CBS 2074 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 (S)-2-Phenyl-propionic acid (R)-2,2,2-trifluoro-1-((R)-phenyl-phenylsulfanyl-methyl)-ethyl ester
  参考文献：
  名称：

  微生物还原α，α，α-三氟-α'-亚磺酰基酮

  摘要：

  几种微生物已被用于还原两个α，α，α-三氟-α′-亚磺酰基酮。它们中的一些在非对映体和对映体的高选择性下产生相应的醇，在生物转化条件下，起始酮的外消旋化确保了单个对映体的高转化率。还描述了所获得的亚磺酰基-三氟甲基-醇向三氟甲基-环氧化物的转化。

  DOI：

  10.1016/0040-4039(96)00685-5
• 作为产物：
  描述：

  (2S,3R)-2-ethoxy-3-phenyl-2-(trifluoromethyl)oxirane 、 苯硫酚 在 六氟异丙醇 作用下， 反应 2.0h， 以82%的产率得到1,1,1-trifluoro-3-phenyl-3-phenylthio-2-propanone
  参考文献：
  名称：

  Comparative study of the ring opening of 1-CF3-epoxy ethers mediated by Brönsted acids and hexafluoro-2-propanol

  摘要：

  In order to evaluate more deeply the nature of the activation of oxirane ring opening reactions by HFIP, ring opening of both CF3-epoxy ethers 1a (R = Ph) and 1b (R = CH2CH2Ph) with HFIP alone, and with hard (MeOH) or soft (PhSH) nucleophiles in HFIP, were investigated and compared to reactions performed with Bronsted acids. Nucleophilic ring opening reactions in HFIP were facilitated with PhSH and only alpha-substituted trifluoromethyl ketone 5 was isolated (nucleophilic ring opening), while with MeOH, both processes, nucleophile and electrophile-assisted ring opening were in competition. In the Bronsted acid-catalysed ring opening of 1-CF3-epoxy ethers 1 in HFIP, only the acid-catalysed ring opening process occurred with an inversed regioselectivity. (c) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.12.008

文献信息

• Synthesis of 3-(Alkylthio and Phenylthio)-1,1,1-trifluoroalkan-2-ones via Ring Opening of Epoxy Ethers
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Andrei Kornilov

  DOI：10.1055/s-1996-4235

  日期：1996.4

  Regioselective ring opening of 1-trifluoromethyl epoxy ethers 2 was achieved with alkyl and phenyl sodium thiolates to afford new 3-(alkylthio and phenylthio)-1,1,1-trifluoroalkan-2-ones 3-5 in good yields.

  1-三氟甲基环氧乙烷2的选择性开环反应通过烷基和苯基硫醇钠实现，以良好产率得到了新型3-(烷硫基和苯硫基)-1,1,1-三氟代烷-2-酮3-5。
• Comparative study of the ring opening of 1-CF3-epoxy ethers mediated by Brönsted acids and hexafluoro-2-propanol
  作者：Jernej Iskra、Danièle Bonnet-Delpon、Jean-Pierre Bégué

  DOI：10.1016/j.jfluchem.2004.12.008

  日期：2005.4

  In order to evaluate more deeply the nature of the activation of oxirane ring opening reactions by HFIP, ring opening of both CF3-epoxy ethers 1a (R = Ph) and 1b (R = CH2CH2Ph) with HFIP alone, and with hard (MeOH) or soft (PhSH) nucleophiles in HFIP, were investigated and compared to reactions performed with Bronsted acids. Nucleophilic ring opening reactions in HFIP were facilitated with PhSH and only alpha-substituted trifluoromethyl ketone 5 was isolated (nucleophilic ring opening), while with MeOH, both processes, nucleophile and electrophile-assisted ring opening were in competition. In the Bronsted acid-catalysed ring opening of 1-CF3-epoxy ethers 1 in HFIP, only the acid-catalysed ring opening process occurred with an inversed regioselectivity. (c) 2004 Elsevier B.V. All rights reserved.
• Microbial reduction of α,α,α-trifluoro-α′-sulfenylketones
  作者：Alberto Arnone、Giuditta Biagini、Rosanna Cardillo、Giuseppe Resnati、Jean-Pierre Bégué、Daniele Bonnet-Delpon、Andrei Kornilov

  DOI：10.1016/0040-4039(96)00685-5

  日期：1996.5

  Several microorganisms have been employed in the reduction of two α,α,α-trifluoro-α′-sulfenylketones. Some of them produce corresponding alcohols in high diastero- and enantioselection, the high conversion in a single enantiomer being secured by the racemization of starting ketones in the biotransformation conditions. Transformation of obtained sulfenyl-trifluoromethyl-alcohols into trifluoromethyl-epoxides

  几种微生物已被用于还原两个α，α，α-三氟-α′-亚磺酰基酮。它们中的一些在非对映体和对映体的高选择性下产生相应的醇，在生物转化条件下，起始酮的外消旋化确保了单个对映体的高转化率。还描述了所获得的亚磺酰基-三氟甲基-醇向三氟甲基-环氧化物的转化。