2,2,2-trifluoro-1-(pyren-1-yl)ethan-1-one | 169295-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2,2,2-trifluoro-1-(pyren-1-yl)ethan-1-one
• 英文别名: 1-(trifluoroacetyl)pyrene；2,2,2-Trifluoro-1-pyren-1-ylethanone
• CAS: 169295-60-7
• 化学式: C₁₈H₉F₃O
• 分子量: 298.264
• InChiKey: ZSOLGSRXUCXTAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  418.6±40.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-1-(pyren-1-yl)ethan-1-one 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (+/-)-2,2,2-trifluoro-1-(1-pyrenyl)ethyl chloroacetate
  参考文献：
  名称：

  Enzymatic Resolution of 2,2,2-Trifluoro-1-(1-pyrenyl)ethanol with Lipases

  摘要：

  利用脂肪酶实现了(±)-2,2,2-三氟-1-(1-芘基)乙醇的光学解析。尤其是铜绿假单胞菌脂肪酶（脂肪酶 LIP）在醇解标题化合物的氯乙酰酯时表现出很高的对映选择性（E = > 100）和反应活性。脂肪酶 LIP 催化的对映体选择性醇解氯乙酸酯与 1-己醇的反应活性远高于醇与乙酸乙烯酯乙酰化的反应活性。

  DOI：

  10.1271/bbb.61.194
• 作为产物：
  描述：

  芘 、 三氟乙酸酐 在 二甲基硫 、 三氟化硼 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到2,2,2-trifluoro-1-(pyren-1-yl)ethan-1-one
  参考文献：
  名称：

  Acylation of activated aromatic substrates under mild conditions with (RCO)2O/Me2S/BF3

  摘要：

  An efficient procedure for acylation and perfluoroacylation of activated aromatic substrates under mild conditions using the system (RCO)(2)O/Me(2)S/BF3 in CH2Cl2 is described. It is believed that dimethylacylsulfonium salts, RCOSMe(2)+ RCO(2)BF(3)-, are the active acylating agents.

  DOI：

  10.1016/0040-4039(95)00699-d

文献信息

• Transition‐Metal‐Free C2‐Functionalization of Pyridines through Aryne Three‐Component Coupling
  作者：Avishek Guin、Subrata Bhattacharjee、Akkattu T. Biju

  DOI：10.1002/chem.202102005

  日期：2021.10

  C2-functionalization of pyridines through a transition-metal-free protocol by using aryne multicomponent coupling is demonstrated. The reaction allowed a broad-scope synthesis of C2-substituted pyridine derivatives bearing the −CF3 group in good yields with α,α,α-trifluoroacetophenones as the third component. Activated keto esters could also be employed as the third component in this formal 1,2-di(hetero)arylation

  展示了通过使用芳炔多组分耦合通过无过渡金属协议直接对吡啶进行 C2 功能化。该反应允许以良好的收率广泛合成带有-CF 3基团的C2-取代的吡啶衍生物，其中α,α,α-三氟苯乙酮作为第三组分。活化的酮酯也可以用作酮的这种正式的 1,2-二（杂）芳基化中的第三组分。在稀释条件下进行反应抑制了竞争性吡啶-芳烃聚合途径。最初生成的亚吡啶中间体对羰基进行亲核攻击，然后进行类似于 Smiles 重排的 S N Ar 过程，得到所需的产物。
• N‐Heterocyclic Carbene‐Catalyzed Formal [6+2] Annulation Reaction via Cross‐Conjugated Aza‐Trienolate Intermediates
  作者：Kuruva Balanna、Krishnaprasad Madica、Subrata Mukherjee、Arghya Ghosh、Thomas Poisson、Tatiana Besset、Garima Jindal、Akkattu T. Biju

  DOI：10.1002/chem.201905177

  日期：2020.1.16

  The diverse reactivity of N-heterocyclic carbenes (NHCs) in organocatalysis is due to the possibility of different modes of action. Although NHC-bound enolates and dienolates are known, the related NHC-bound cross-conjugated aza-trienolates remain elusive. Herein, we demonstrate the NHC-catalyzed formal [6+2] annulation of nitrogen-containing heterocyclic aldehydes with α,α,α-trifluoroacetophenones

  N-杂环卡宾（NHC）在有机催化中的不同反应性是由于可能存在不同作用方式的缘故。尽管已知与NHC结合的烯酸酯和二烯酸酯，但相关的与NHC结合的交叉偶联的氮杂三烯酸酯仍然难以捉摸。在这里，我们证明了NHC催化的含氮杂环醛与[α，α，α-三氟苯乙酮]的正式[6 + 2]环化反应，导致形成通用的吡咯并恶唑酮（29个例子）。催化生成的交叉共轭氮杂三烯酸酯（氮杂富烯型）与亲电子酮进行平稳的[6 + 2]环合，在温和条件下以中等至良好的收率得到产物。还提供了有关该机制的初步DFT研究。
• Preparation and behavior of (R)- and (S)-2,2,2-trifluoro-1-(1-pyrenyl)ethanol as chiral solvating agents: study of the diastereomeric association by Job's plots, intermolecular NOE and binding constants
  作者：Anna Muñoz、Albert Virgili

  DOI：10.1016/s0957-4166(02)00370-1

  日期：2002.8

  Racemic 2,2,2-trifluoro-1-(1-pyrenyl)ethanol 2, was prepared and the (R)- and (S)-enantiomers obtained by preparative chiral HPLC. The behavior of these compounds as chiral solvating agents is studied with mixtures of several enantiomeric aromatic alcohols and amines. The non-linear distribution of aromatic rings in the pyrene appears to enhance the enantiodiscrimination capacity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Acylation of activated aromatic substrates under mild conditions with (RCO)2O/Me2S/BF3
  作者：Alexander S. Kiselyov、Ronald G. Harvey

  DOI：10.1016/0040-4039(95)00699-d

  日期：1995.6

  An efficient procedure for acylation and perfluoroacylation of activated aromatic substrates under mild conditions using the system (RCO)(2)O/Me(2)S/BF3 in CH2Cl2 is described. It is believed that dimethylacylsulfonium salts, RCOSMe(2)+ RCO(2)BF(3)-, are the active acylating agents.
• Enzymatic Resolution of 2,2,2-Trifluoro-1-(1-pyrenyl)ethanol with Lipases
  作者：Katsuya Kato、Masato Katayama、Shozo Fujii、Hiroshi Kimoto

  DOI：10.1271/bbb.61.194

  日期：1997.1

  The optical resolution of (±)-2,2,2-trifluoro-1-(1-pyrenyl)ethanol was achieved by using lipases. In particular, Pseudomonas aeruginosa lipase (lipase LIP) showed high enantioselectivity (E = > 100) and reactivity in the alcoholysis of the chloroacetyl ester of the title compound. The reactivity of the lipase LIP-catalyzed enantioselective alcoholysis of the chloroacetate with 1-hexanol was much higher than that of the acetylating the alcohol with vinyl acetate.

  利用脂肪酶实现了(±)-2,2,2-三氟-1-(1-芘基)乙醇的光学解析。尤其是铜绿假单胞菌脂肪酶（脂肪酶 LIP）在醇解标题化合物的氯乙酰酯时表现出很高的对映选择性（E = > 100）和反应活性。脂肪酶 LIP 催化的对映体选择性醇解氯乙酸酯与 1-己醇的反应活性远高于醇与乙酸乙烯酯乙酰化的反应活性。