2-methyl-N-(2-methylquinolin-8-yl)benzamide | 438471-63-7

• 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: 2-methyl-N-(2-methylquinolin-8-yl)benzamide
• CAS: 438471-63-7
• 化学式: C₁₈H₁₆N₂O
• mdl: MFCD02605614
• 分子量: 276.338
• InChiKey: JUUQGRGXLKFGCU-UHFFFAOYSA-N

物化性质

• 沸点：
  387.1±30.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-N-(2-methylquinolin-8-yl)benzamide 、 三甲基铝 以 甲苯 为溶剂， 以85.2%的产率得到dimethylaluminum 2-methyl-N-(2-methylquinolin-8-yl)benzamidate
  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
• 作为产物：
  描述：

  对甲苯甲酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-methyl-N-(2-methylquinolin-8-yl)benzamide
  参考文献：
  名称：

  铑催化含炔烃的芳酰胺中C–H键的烯基化

  摘要：

  据报道，铑通过炔烃催化芳族酰胺的C–H键的烯基化。包括OMe，OAc，Br，Cl甚至NO 2在内的各种官能团均适用于该反应，以生成相应的氢芳基化产物。8-氨基喹啉基团作为导向基团的存在对于反应成功至关重要。

  DOI：

  10.1021/acs.orglett.7b00709

文献信息

• Rhodium-Catalyzed Alkenylation of C–H Bonds in Aromatic Amides with Alkynes
  作者：Kaname Shibata、Satoko Natsui、Naoto Chatani

  DOI：10.1021/acs.orglett.7b00709

  日期：2017.5.5

  The rhodium-catalyzed alkenylation of C–H bonds of aromatic amides with alkynes is reported. A variety of functional groups, including OMe, OAc, Br, Cl, and even NO2, are applicable to this reaction to give the corresponding hydroarylation products. The presence of an 8-aminoquinoline group as the directing group is crucial for the success of the reaction.

  据报道，铑通过炔烃催化芳族酰胺的C–H键的烯基化。包括OMe，OAc，Br，Cl甚至NO 2在内的各种官能团均适用于该反应，以生成相应的氢芳基化产物。8-氨基喹啉基团作为导向基团的存在对于反应成功至关重要。
• 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.