1-(3-(二甲基氨基)苯基)-2,2,2-三氟乙酮 | 33284-23-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3-(二甲基氨基)苯基)-2,2,2-三氟乙酮
• 英文名称: 2,2,2-trifluoro-1-(3-dimethylaminophenyl)ethanone
• 英文别名: 3-N,N-dimethylanilinyl trifluoromethyl ketone；N.N-Dimethylanilyl-3-trifluormethylketon；1-(3-(Dimethylamino)phenyl)-2,2,2-trifluoroethanone；1-[3-(dimethylamino)phenyl]-2,2,2-trifluoroethanone
• CAS: 33284-23-0
• 化学式: C₁₀H₁₀F₃NO
• 分子量: 217.191
• InChiKey: ZMHBSXYQECXIJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2922399090

反应信息

• 作为反应物：
  描述：

  1-(3-(二甲基氨基)苯基)-2,2,2-三氟乙酮 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 0.5h， 生成 1-(3-Dimethylamino-phenyl)-2,2,2-trifluoro-ethanol
  参考文献：
  名称：

  m-(N,N,N-Trimethylammonio)trifluoroacetophenone: a femtomolar inhibitor of acetylcholinesterase

  摘要：

  m-(N,N,N-Trimethylammonio)trifluoroacetophenone is a potent, reversible, time-dependent inhibitor of acetylcholinesterases. The respective second-order rate constants (k(on)) for binding of the ketone to enzymes from Electrophorus electricus and Torpedo californica are (1.2 +/- 0.2) X 10(5) and (1.0 + 0.2) X 10(5) M-1 s-1, while the corresponding dissociation rate constants (k(off)) are (1.0 +/- 0.2) X 10(-5) and (1.0 +/- 0.3) X 10(-4) s-1. Therefore, the apparent dissociation constants of the enzyme-inhibitor complexes (K(i)app = k(off)/k(on)) are 80 +/- 20 pM and 1.0 +/- 0.3 nM, respectively. Because the free ketone is the form that inhibits acetylcholinesterases, intrinsic dissociation constants were calculated by correcting the K(i)app values for the extent of hydration of the inhibitor. The resulting K(i) values are 1.3 and 15 fM for inhibitions of E. electricus and T. californica acetylcholinesterases, respectively.

  DOI：

  10.1021/ja00075a009
• 作为产物：
  描述：

  间溴苯胺 在 氢氧化钾 、 叔丁基锂 作用下， 以 水 为溶剂， 反应 3.0h， 生成 1-(3-(二甲基氨基)苯基)-2,2,2-三氟乙酮
  参考文献：
  名称：

  m-(N,N,N-Trimethylammonio)trifluoroacetophenone: a femtomolar inhibitor of acetylcholinesterase

  摘要：

  m-(N,N,N-Trimethylammonio)trifluoroacetophenone is a potent, reversible, time-dependent inhibitor of acetylcholinesterases. The respective second-order rate constants (k(on)) for binding of the ketone to enzymes from Electrophorus electricus and Torpedo californica are (1.2 +/- 0.2) X 10(5) and (1.0 + 0.2) X 10(5) M-1 s-1, while the corresponding dissociation rate constants (k(off)) are (1.0 +/- 0.2) X 10(-5) and (1.0 +/- 0.3) X 10(-4) s-1. Therefore, the apparent dissociation constants of the enzyme-inhibitor complexes (K(i)app = k(off)/k(on)) are 80 +/- 20 pM and 1.0 +/- 0.3 nM, respectively. Because the free ketone is the form that inhibits acetylcholinesterases, intrinsic dissociation constants were calculated by correcting the K(i)app values for the extent of hydration of the inhibitor. The resulting K(i) values are 1.3 and 15 fM for inhibitions of E. electricus and T. californica acetylcholinesterases, respectively.

  DOI：

  10.1021/ja00075a009

文献信息

• Fluoroform: an Efficient Precursor for the Trifluoromethylation of Aromatic Esters by Sodium Diisopropylamide with Trialkylamines
  作者：Zhaomeng Han、Sihan Chen、Yongjun Tu、Xiongdong Lian、Gongyong Li

  DOI：10.1002/ejoc.201900250

  日期：2019.8.7

  for the first time by using trialkylamines as cation chelating‐agents to stabilize the isolated –CF3 ion to realize trifluoromethylation reaction. With this strategy, trifluoromethyl aromatic ketones could be effectively synthesized from fluoroform and aromatic esters with diisopropyl aminosodium (NaDA) and trialkylamines.

  短文本：该trifluoromethanide阴离子是首次通过使用三烷基胺如阳离子螯合剂剂以稳定分离制备- CF 3离子，实现三氟甲基化反应。通过这种策略，可以从氟仿和芳族酯与二异丙基氨基钠（NaDA）和三烷基胺有效地合成三氟甲基芳族酮。
• Continuous-Flow Synthesis of Perfluoroalkyl Ketones via Perfluoroalkylation of Esters Using HFC-23 and HFC-125 under a KHMDS–Triglyme System
  作者：Yamato Fujihira、Hiroto Iwasaki、Yuji Sumii、Hiroaki Adachi、Takumi Kagawa、Norio Shibata

  DOI：10.1246/bcsj.20220162

  日期：2022.9.15

  chemical transformation of two HFCs, viz. HFC-23 and HFC-125, based on the continuous-flow perfluoroalkylation of esters to synthesize the pharmaceutically and agrochemically vital trifluoromethyl and pentafluoroethyl ketones. The combination of a potassium base and a glyme solvent system is found to be the most effective. The proposed method is attractive for industrial use because it allows the consumption

  氢氟烃 (HFC) 广泛用作冰箱和空调中的冷却剂以及工业过程中的溶剂。然而，它们的应用受到其高全球变暖潜能值的限制。因此，迫切需要 HFC 分解和有效利用的策略。在这里，我们描述了两种 HFC 的化学转化方法，即。HFC-23 和 HFC-125，基于酯的连续流动全氟烷基化合成医药和农业化学重要的三氟甲基和五氟乙基酮。发现钾碱和甘醇二甲醚溶剂系统的组合是最有效的。所提出的方法对工业用途很有吸引力，因为它可以消耗大量的 HFC，促进高价值药用化合物的合成，
• Pyridyl and N,N-dimethylanilyltrifluoromethylketones forming stable gem-diols
  作者：R.L. Salvador、M. Saucier

  DOI：10.1016/s0040-4020(01)90870-1

  日期：1971.1
• Development of acetophenone ligands as potential neuroimaging agents for cholinesterases
  作者：Courtney T. Jollymore-Hughes、Ian R. Pottie、Earl Martin、Terrone L. Rosenberry、Sultan Darvesh

  DOI：10.1016/j.bmc.2016.08.048

  日期：2016.11

  Association of cholinesterase with beta-amyloid plaques and tau neurofibrillary tangles in Alzheimer's disease offers an opportunity to detect disease pathology during life. Achieving this requires development of radiolabelled cholinesterase ligands with high enzyme affinity. Various fluorinated acetophenone derivatives bind to acetylcholinesterase with high affinity, including 2,2,2-trifluoro-1-(3-dimethylaminophenyl)ethanone (1) and 1-(3-tert-butylphenyl)-2,2,2-trifluoroethanone (2). Such compounds also offer potential for incorporation of radioactive fluorine (F-18) for Positron Emission Tomography (PET) imaging of cholinesterases in association with Alzheimer's disease pathology in the living brain. Here we describe the synthesis of two meta-substituted chlorodifluoroacetophenones using a Weinreb amide strategy and their rapid conversion to the corresponding trifluoro derivatives through nucleophilic substitution by fluoride ion, in a reaction amenable to incorporating F-18 for PET imaging. In vitro kinetic analysis indicates tight binding of the trifluoro derivatives to cholinesterases. Compound 1 has a K-i value of 7 nM for acetylcholinesterase and 1300 nM for butyrylcholinesterase while for compound 2 these values are 0.4 nM and 26 nM, respectively. Tight binding of these compounds to cholinesterase encourages their development for PET imaging detection of cholinesterase associated with Alzheimer's disease pathology. (C) 2016 Elsevier Ltd. All rights reserved.
• KOCHEVA, L. V.
  作者：KOCHEVA, L. V.

  DOI：——

  日期：——