2,2,2-trifluoro-1-(1-(pentan-3-yl)-1H-pyrazol-4-yl)ethanone | 1506300-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-trifluoro-1-(1-(pentan-3-yl)-1H-pyrazol-4-yl)ethanone
• 英文别名: 2,2,2-Trifluoro-1-(1-pentan-3-ylpyrazol-4-yl)ethanone；2,2,2-trifluoro-1-(1-pentan-3-ylpyrazol-4-yl)ethanone
• CAS: 1506300-86-2
• 化学式: C₁₀H₁₃F₃N₂O
• 分子量: 234.221
• InChiKey: YYGHBQVPXHKCRO-UHFFFAOYSA-N

物化性质

• 沸点：
  258.8±35.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-1-(1-(pentan-3-yl)-1H-pyrazol-4-yl)ethanone 在 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 、 水 、 重水 作用下， 以 乙酸乙酯 为溶剂， 反应 90.0h， 生成 C₁₀H₁₃⁽²⁾H₂FN₂O
  参考文献：
  名称：

  氟代烷基酮渐进式（氘代）加氢脱氟的卡宾策略

  摘要：

  报道了一种用于氟代烷基酮顺序（氘代）加氢脱氟的卡宾策略。该方法允许从芳基和烷基取代的全氟烷基酮以高产率可控制备二氟烷基酮和单氟烷基酮，并具有优异的官能团耐受性。

  DOI：

  10.1002/anie.202116190
• 作为产物：
  描述：

  三氟乙酸甲酯 、 4-Bromo-1-pentan-3-ylpyrazole 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以67%的产率得到2,2,2-trifluoro-1-(1-(pentan-3-yl)-1H-pyrazol-4-yl)ethanone
  参考文献：
  名称：

  Difluoromethyl ketones: Potent inhibitors of wild type and carbamate-insensitive G119S mutant Anopheles gambiae acetylcholinesterase

  摘要：

  Malaria is a devastating disease in sub-Saharan Africa, and current vector control measures are threatened by emerging resistance mechanisms. With the goal of developing new, selective, resistance-breaking insecticides we explored alpha-fluorinated methyl ketones as reversible covalent inhibitors of Anopheles gambiae acetylcholinesterase (AgAChE). Trifluoromethyl ketones 5 demonstrated remarkable volatility in microtiter plate assays, but 5c,e-h exhibited potent (1-100 nM) inhibition of wild type (WT) AgAChE and weak inhibition of resistant mutant G119S mutant AgAChE. Fluoromethyl ketones 10c-i exhibited submicromolar to micromolar inhibition of WT AgAChE, but again only weakly inhibited G119S AgAChE. Interestingly, difluoromethyl ketone inhibitors 9c and 9g had single digit nanomolar inhibition of WT AgAChE, and 9g had excellent potency against G119S AgAChE. Approach to steady-state inhibition was quite slow, but after 23 h incubation an IC50 value of 25.1 +/- 1.2 nM was measured. We attribute the slow, tight-binding G119S AgAChE inhibition of 9g to a balance of steric size and electrophilicity. However, toxicities of 5g, 9g, and 10g to adult A. gambiae in tarsal contact, fumigation, and injection assays were lower than expected based on WT AgAChE inhibition potency and volatility. Potential toxicity-limiting factors are discussed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.019

文献信息

• Direct electrochemical hydrodefluorination of trifluoromethylketones enabled by non-protic conditions
  作者：John R. Box、Alexander P. Atkins、Alastair J. J. Lennox

  DOI：10.1039/d1sc01574e

  日期：——

  The electrochemical hydrodefluorination of trifluoromethylketones under non-protic conditions make this single-step reaction at deeply reductive potentials uniquely amenable to challenging electron-rich substrates and reductively sensitive functionalities.

  三氟甲基酮在非质子条件下的电化学脱氟反应使得这种单步反应在深度还原电位下对富电子底物和还原敏感官能团具有独特的适应性。
• Direct Noncatalytic Electrophilic Trifluoroacetylation of Electron-Rich Pyrazoles
  作者：Pavel Mykhailiuk、Dmytro Yarmoliuk、Viatcheslav Arkhipov、Maksym Stambirskyi、Yurii Dmytriv、Oleg Shishkin、Andrei Tolmachev

  DOI：10.1055/s-0033-1340840

  日期：——

  Abstract Electron-rich N-substituted pyrazoles smoothly reacted with trifluoroacetic anhydride in pyridine to form the corresponding trifluoromethyl ketones in good yields. Electron-rich N-substituted pyrazoles smoothly reacted with trifluoroacetic anhydride in pyridine to form the corresponding trifluoromethyl ketones in good yields.

  摘要 富电子的N-取代的吡唑与吡啶中的三氟乙酸酐平稳反应，以高收率形成相应的三氟甲基酮。 富电子的N-取代的吡唑与吡啶中的三氟乙酸酐平稳反应，以高收率形成相应的三氟甲基酮。
• Difluoromethyl ketones: Potent inhibitors of wild type and carbamate-insensitive G119S mutant Anopheles gambiae acetylcholinesterase
  作者：Eugene Camerino、Dawn M. Wong、Fan Tong、Florian Körber、Aaron D. Gross、Rafique Islam、Elisabet Viayna、James M. Mutunga、Jianyong Li、Maxim M. Totrov、Jeffrey R. Bloomquist、Paul R. Carlier

  DOI：10.1016/j.bmcl.2015.09.019

  日期：2015.10

  Malaria is a devastating disease in sub-Saharan Africa, and current vector control measures are threatened by emerging resistance mechanisms. With the goal of developing new, selective, resistance-breaking insecticides we explored alpha-fluorinated methyl ketones as reversible covalent inhibitors of Anopheles gambiae acetylcholinesterase (AgAChE). Trifluoromethyl ketones 5 demonstrated remarkable volatility in microtiter plate assays, but 5c,e-h exhibited potent (1-100 nM) inhibition of wild type (WT) AgAChE and weak inhibition of resistant mutant G119S mutant AgAChE. Fluoromethyl ketones 10c-i exhibited submicromolar to micromolar inhibition of WT AgAChE, but again only weakly inhibited G119S AgAChE. Interestingly, difluoromethyl ketone inhibitors 9c and 9g had single digit nanomolar inhibition of WT AgAChE, and 9g had excellent potency against G119S AgAChE. Approach to steady-state inhibition was quite slow, but after 23 h incubation an IC50 value of 25.1 +/- 1.2 nM was measured. We attribute the slow, tight-binding G119S AgAChE inhibition of 9g to a balance of steric size and electrophilicity. However, toxicities of 5g, 9g, and 10g to adult A. gambiae in tarsal contact, fumigation, and injection assays were lower than expected based on WT AgAChE inhibition potency and volatility. Potential toxicity-limiting factors are discussed. (C) 2015 Elsevier Ltd. All rights reserved.
• A Carbene Strategy for Progressive (Deutero)Hydrodefluorination of Fluoroalkyl Ketones
  作者：Xiaolong Zhang、Xinyu Zhang、Qingmin Song、Paramasivam Sivaguru、Zikun Wang、Giuseppe Zanoni、Xihe Bi

  DOI：10.1002/anie.202116190

  日期：2022.2.7

  A carbene strategy for the sequential (deutero)hydrodefluorination of fluoroalkyl ketones is reported. This method allowed for the controllable preparation of difluoroalkyl- and monofluoroalkyl ketones from aryl- and alkyl-substituted perfluoroalkyl ketones in high yield with excellent functional group tolerance.

  报道了一种用于氟代烷基酮顺序（氘代）加氢脱氟的卡宾策略。该方法允许从芳基和烷基取代的全氟烷基酮以高产率可控制备二氟烷基酮和单氟烷基酮，并具有优异的官能团耐受性。