N-(2-methylquinolin-8-yl)-2,2,2-trifluoroacetamide | 444935-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(2-methylquinolin-8-yl)-2,2,2-trifluoroacetamide
• 英文别名: 2,2,2-trifluoro-N-(2-methylquinolin-8-yl)acetamide；2,2,2-trifluoro-N-(2-methyl-8-quinolinyl)acetamide
• CAS: 444935-89-1
• 化学式: C₁₂H₉F₃N₂O
• mdl: MFCD02606049
• 分子量: 254.211
• InChiKey: OQPXWXNHOKPRTE-UHFFFAOYSA-N

物化性质

• 沸点：
  370.8±42.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-methylquinolin-8-yl)-2,2,2-trifluoroacetamide 、 四苯硼钠 在 碘 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以78%的产率得到(κ²-(N,N′)-2-methyl-8-trifluoroacetylaminoquinolate) diphenylborane
  参考文献：
  名称：

  Iodine-Catalyzed Synthesis of N,N′-Chelate Organoboron Aminoquinolate

  摘要：

  We disclose a novel method for the synthesis of fluorescent N, N'-chelate organoboron compounds in high efficiency by treatment of aminoquinolates with NaBAr4/R'COOH in the presence of an iodine catalyst. These compounds display high air and thermal stability. A possible catalytic mechanism based on the results of control experiments has been proposed. Fluorescence quantum yield of 3b is up to 0.79 in dichloromethane.

  DOI：

  10.1021/acs.joc.0c01649
• 作为产物：
  描述：

  8-氨基喹哪啶 、 三氟乙酸 在 三氯化磷 作用下， 以 甲苯 为溶剂， 反应 6.25h， 以80.1%的产率得到N-(2-methylquinolin-8-yl)-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Synthesis and Characterization of Dialkylaluminum Amidates and Their Ring-Opening Polymerization of ε-Caprolactone

  摘要：

  The stoichiometric reactions of N-(2-methylquinolin-8-yl) (R)amides (L1-L8; L1, R = Ph; L2, R = p-FPh; L3, R = p-ClPh; L4, R = p-(MeO)Ph; L5, R = o-MePh; L6, R = p-MePh; L7, R = Me; L8, R = CF3) with Me3Al afforded the corresponding dimethylaluminum amidate complexes [Me2AlL] (C1-C8). The treatment of N-(2-methylquinolin-8-yl)picolinamide (L9) with 1 or 2 equiv of Me3Al formed Me(2)AlL9 (C9) or Me(2)AlL9 center dot Me(3)A1 (C10), respectively; meanwhile, the stoichiometric reaction of L9 with iBu(3)Al gave iBu(2)AlL9 (C11). All organoaluminum amidate complexes were fully characterized by H-1/C-13 NMR spectroscopy and elemental analysis, and the unambiguous structures of complexes C2, C4, C9, and C11 were further determined by single-crystal X-ay diffraction. With the assistance of 1 equiv of BnOH, all dialkylaluminum amidate complexes showed appreciable activities toward the ring-opening polymerization of epsilon-caprolactone and produced polycaprolactones with narrow polydispersity; the nature of the active species was also investigated.

  DOI：

  10.1021/om2008343

文献信息

• 一种新型外消旋手性有机硼氮荧光化合物及 其制备方法
  申请人：湖南大学

  公开号：CN107338043B

  公开（公告）日：2020-04-24

  本发明为一种新型手性有机硼氮荧光化合物及其制备方法。其特征在于，以喹啉酰胺化合物、廉价的四苯硼钠类衍生物、羧酸类衍生物为原料，以廉价、易得的单质碘作为催化剂，以常用的有机溶剂作反应溶剂，反应在一定温度下反应一定时间，高产率、高选择性地得到一种新型手性有机硼氮荧光化合物。该催化剂稳定性好，可回收，并且在醛酮缩合反应中有非常好的非对应异构选择性。本方法具有成本较低，产率高，操作简便、无污染等优点，对于实现其工业化生产具有一定的可行性。
• Carbon–Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)–CF₃ Bond Cleavage
  作者：Longzhi Zhu、Liyuan Le、Mingpan Yan、Chak-Tong Au、Renhua Qiu、Nobuaki Kambe

  DOI：10.1021/acs.joc.9b00583

  日期：2019.5.3

  The reaction of trifluoroacetyl amides with Grignard reagent for the substitution of CF3 group with various alkyl or aryl groups is described. A variety of aryl, quinolin-8-yl, and (hetero)alkyl functional groups as well as F, Cl, and Br atoms are well tolerated. These moisture-stable and easily available trifluoroacetyl amides can be conveniently obtained and used as new versatile precursors for isocyanates

  描述了三氟乙酰酰胺与格氏试剂的反应，以用各种烷基或芳基取代CF 3基团。各种芳基，喹啉-8-基和（杂）烷基官能团以及F，Cl和Br原子均具有良好的耐受性。这些水分稳定且易于获得的三氟乙酰基酰胺可以方便地获得，并用作异氰酸酯的新型通用前体。对照实验表明，反应是通过异氰酸酯中间体和/或醇盐/酰胺双阴离子中间体进行的。
• Iodine-Catalyzed Synthesis of <i>N,N</i>′-Chelate Organoboron Aminoquinolate
  作者：Tianbao Yang、Xin Cao、Xing-Xing Zhang、Yifeng Ou、Chak-Tong Au、Shuang-Feng Yin、Renhua Qiu

  DOI：10.1021/acs.joc.0c01649

  日期：2020.10.2

  We disclose a novel method for the synthesis of fluorescent N, N'-chelate organoboron compounds in high efficiency by treatment of aminoquinolates with NaBAr4/R'COOH in the presence of an iodine catalyst. These compounds display high air and thermal stability. A possible catalytic mechanism based on the results of control experiments has been proposed. Fluorescence quantum yield of 3b is up to 0.79 in dichloromethane.
• Synthesis and Characterization of Dialkylaluminum Amidates and Their Ring-Opening Polymerization of ε-Caprolactone
  作者：Wenjuan Zhang、Youhong Wang、Ji Cao、Lin Wang、Yi Pan、Carl Redshaw、Wen-Hua Sun

  DOI：10.1021/om2008343

  日期：2011.11.28

  The stoichiometric reactions of N-(2-methylquinolin-8-yl) (R)amides (L1-L8; L1, R = Ph; L2, R = p-FPh; L3, R = p-ClPh; L4, R = p-(MeO)Ph; L5, R = o-MePh; L6, R = p-MePh; L7, R = Me; L8, R = CF3) with Me3Al afforded the corresponding dimethylaluminum amidate complexes [Me2AlL] (C1-C8). The treatment of N-(2-methylquinolin-8-yl)picolinamide (L9) with 1 or 2 equiv of Me3Al formed Me(2)AlL9 (C9) or Me(2)AlL9 center dot Me(3)A1 (C10), respectively; meanwhile, the stoichiometric reaction of L9 with iBu(3)Al gave iBu(2)AlL9 (C11). All organoaluminum amidate complexes were fully characterized by H-1/C-13 NMR spectroscopy and elemental analysis, and the unambiguous structures of complexes C2, C4, C9, and C11 were further determined by single-crystal X-ay diffraction. With the assistance of 1 equiv of BnOH, all dialkylaluminum amidate complexes showed appreciable activities toward the ring-opening polymerization of epsilon-caprolactone and produced polycaprolactones with narrow polydispersity; the nature of the active species was also investigated.