1-phenyl-3-(phenylamino)-3-(4-(trifluoromethyl)-phenyl)propan-1-one | 821794-46-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-phenyl-3-(phenylamino)-3-(4-(trifluoromethyl)-phenyl)propan-1-one
• 英文别名: 3-[4-(trifluoromethyl)phenyl]-1-phenyl-3-(phenylamino)propan-1-one；1-Propanone, 1-phenyl-3-(phenylamino)-3-[4-(trifluoromethyl)phenyl]-；3-anilino-1-phenyl-3-[4-(trifluoromethyl)phenyl]propan-1-one
• CAS: 821794-46-1
• 化学式: C₂₂H₁₈F₃NO
• 分子量: 369.386
• InChiKey: DYYMEEJSEJHPOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 苯胺 、 苯乙酮 在 [{CH₃CpZr(OH₂)₃}₂(μ²-OH)₂][OSO₂C₈F₁₇]₄ 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以98%的产率得到1-phenyl-3-(phenylamino)-3-(4-(trifluoromethyl)-phenyl)propan-1-one
  参考文献：
  名称：

  合成和空气稳定的结构μ 2 -羟基桥连双核络合物的双（甲基环戊二烯基）dizirconium（IV）全氟辛烷磺酸盐及其在路易斯酸催化的反应中的应用

  摘要：

  通过（CH 3 Cp）2 ZrCl 2与C 8 F 17 SO 3 Ag反应成功地合成了双（甲基环戊二烯基）全氟辛烷磺酸锆（1a）的空气稳定双核络合物。化合物1a用不同的技术表征，发现具有空气稳定性，耐水性，热稳定性和强路易斯酸度的性质。此外，它的溶解度高于我们先前报道的单核锆茂双（全氟辛烷磺酸盐）的溶解度。它在烷基芳基醚的Friedel-Crafts酰化反应和Mannich反应中显示出很高的催化效率，可以重复使用。

  DOI：

  10.1016/j.jorganchem.2013.10.004

文献信息

• Strong Lewis Acids of Air-Stable Metallocene Bis(perfluorooctanesulfonate)s as High-Efficiency Catalysts for Carbonyl-Group Transformation Reactions
  作者：Renhua Qiu、Xinhua Xu、Lifeng Peng、Yalei Zhao、Ningbo Li、Shuangfeng Yin

  DOI：10.1002/chem.201103874

  日期：2012.5.14

  that 2 a and 2 b were thermally stable at 300 and 180 °C, respectively. These complexes exhibited unusually high solubility in polar organic solvents. Conductivity measurement showed that the complexes (2 a and 2 b) were ionic dissociation in CH3CN solution. X‐ray analysis result confirmed 2 a⋅3 H2O⋅THF was a cationic organometallic Lewis acid. UV/Vis spectra showed a significant red shift due to the

  强路易斯酸空气中稳定的金属茂双（全氟辛烷磺酸盐）S [M（CP）2 ] [OSO 2 C ^ 8 ˚F 17 ] 2 ⋅ Ñ ħ 2 O⋅THF（M = Zr的（2 ⋅3ħ 2 O⋅THF ），M =的Ti（图2b ⋅2ħ 2 O⋅THF））由[M（CP）的反应合成2 ]氯2（M = Zr的（1），M =的Ti（图1b）），与n BuLi和C 8 F 17 SO 3 H（2当量）或与C 8 F 17 SO 3Ag（2当量）。这些配合物的水合物数（n）是可变的，取决于条件从0变为4。与众所周知的茂金属三氟甲磺酸盐相反，这些络合物在露天环境中一年没有变化。热重-差示扫描量热（TG-DSC）分析表明，2和图2b分别为300和180℃，是热稳定的。这些配合物在极性有机溶剂中显示出异常高的溶解度。电导率测量表明，络合物（2a和2b）在CH 3 CN溶液中呈离子离解。X射线分析结果确认为2 a⋅3H
• An efficient and mild bismuth triflate-catalysed three-component Mannich-type reaction
  作者：Thierry Ollevier、Etienne Nadeau

  DOI：10.1039/b710794c

  日期：——

  In the presence of a catalytic amount of Bi(OTf)(3).4H(2)O, aldehydes together with amines react with silyl enolates to afford the corresponding Mannich-type adducts smoothly. A wide variety of silyl enolates derived from ketones, as well as esters and thioesters, react rapidly to afford the beta-amino ketones or the beta-amino esters in high yields (up to 94%).

  在催化量的Bi（OTf）（3）.4H（2）O的存在下，醛与胺一起与甲硅烷基烯醇酸酯反应，可平稳地提供相应的曼尼希型加合物。多种衍生自酮以及酯和硫代酯的甲硅烷基烯醇化物迅速反应，以高收率（高达94％）提供β-氨基酮或β-氨基酯。
• Bismuth Triflate-Catalyzed Three-Component Mannich-Type Reaction
  作者：Thierry Ollevier、Etienne Nadeau

  DOI：10.1021/jo048617c

  日期：2004.12.1

  Bismuth triflate catalyzes the Mannich-type reaction of a variety of in situ generated aldimines using aldehydes, anilines, and silyl enol ethers in a three-component reaction. The reaction proceeds rapidly and affords the corresponding protected β-amino ketones in high yields (up to 94%).

  在三组分反应中，使用醛，苯胺和甲硅烷基烯醇醚，三氟甲基磺酸铋催化多种原位生成的醛亚胺的曼尼希型反应。反应迅速进行，并以高收率（高达94％）提供相应的被保护的β-氨基酮。
• Synthesis and structure of an air-stable organoantimony complex and its use as a catalyst for direct diastereoselective Mannich reactions in water
  作者：Jun Xia、Renhua Qiu、Shuangfeng Yin、Xiaowen Zhang、Shenglian Luo、Chak-Tong Au、Kai Xia、Wai-Yeung Wong

  DOI：10.1016/j.jorganchem.2010.03.003

  日期：2010.5

  An air-stable organoantimony complex with a 5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine framework was synthesized, characterized, and found to exhibit high catalytic efficiency towards one-pot Mannich reaction with high diastereoselectivity in water. The catalyst can be recycled 10 times without showing any appreciable loss of efficiency. This catalytic system affords a simple and efficient approach for the synthesis of beta-amino ketones. (C) 2010 Elsevier B.V. All rights reserved.
• Synthesis and structure of an air-stable μ2-hydroxy-bridged binuclear complex of bis(methylcyclopentadienyl)dizirconium(IV) perfluorooctanesulfonate and its application in Lewis acid-catalyzed reactions
  作者：Xiaohong Zhang、Cong Lou、Ningbo Li、Xinhua Xu、Renhua Qiu、Shuangfeng Yin

  DOI：10.1016/j.jorganchem.2013.10.004

  日期：2014.1

  Air-stable binuclear complex of bis(methylcyclopentadienyl)zirconium perfluorooctanesulfonate (1a) was successfully synthesized by the reaction of (CH3Cp)2ZrCl2 with C8F17SO3Ag. The compound 1a was characterized by different techniques and found to have the nature of air-stability, water tolerance, thermally-stability and strong Lewis-acidity. In addition, its solubility was higher than that of our

  通过（CH 3 Cp）2 ZrCl 2与C 8 F 17 SO 3 Ag反应成功地合成了双（甲基环戊二烯基）全氟辛烷磺酸锆（1a）的空气稳定双核络合物。化合物1a用不同的技术表征，发现具有空气稳定性，耐水性，热稳定性和强路易斯酸度的性质。此外，它的溶解度高于我们先前报道的单核锆茂双（全氟辛烷磺酸盐）的溶解度。它在烷基芳基醚的Friedel-Crafts酰化反应和Mannich反应中显示出很高的催化效率，可以重复使用。