4-methyl-N-(2-methylquinolin-8-yl)benzamide | 901350-67-2

• 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: 4-methyl-N-(2-methylquinolin-8-yl)benzamide
• CAS: 901350-67-2
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: XKIARZIYZHIDIB-UHFFFAOYSA-N

物化性质

• 沸点：
  388.4±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：

  4-methyl-N-(2-methylquinolin-8-yl)benzamide 在 Iron(III) nitrate nonahydrate 、 copper(II) choride dihydrate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 5.0h， 以70%的产率得到4-methyl-N-(2-methyl-5,7-dinitroquinolin-8-yl)benzamide
  参考文献：
  名称：

  以Fe（NO 3）3 ·9H 2 O为促进剂和硝基源的8-氨基喹啉酰胺的区域和化学选择性单和双硝化反应

  摘要：

  通过使用经济，无毒的Fe（NO 3）3 ·9H 2 O作为促进剂和硝基源，开发了一种高效且区域选择性的8-氨基喹啉酰胺远程C（5）–H硝化方法。此外，当使用CuCl 2 ·2H 2 O作为催化剂时，主要将8-氨基喹啉酰胺进行双硝化以得到5,7-二硝基-8-氨基喹啉酰胺。值得注意的是，这是第一个例子，其中Fe（NO 3）3 ·9H 2 O既起螯合促进剂又起硝化剂的双重作用，而CuCl 2 ·2H 2 O则起喹啉双硝化的有效催化剂的作用。

  DOI：

  10.1021/acs.orglett.6b02998
• 作为产物：
  描述：

  8-氨基喹哪啶 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-methyl-N-(2-methylquinolin-8-yl)benzamide
  参考文献：
  名称：

  与格氏试剂通过C（O）-CF 3键裂解形成三氟乙酰酰胺的碳-碳键形成

  摘要：

  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。

  DOI：

  10.1021/acs.joc.9b00583

文献信息

• Trimetallic yttrium N-(2-methylquinolin-8-yl)benzamides: synthesis, structure and use in ring-opening polymerization (ROP) of ε-caprolactone
  作者：Wenjuan Zhang、Shaofeng Liu、Wen-Hua Sun、Xiang Hao、Carl Redshaw

  DOI：10.1039/c2nj40711f

  日期：——

  A series of trimetallic yttrium complexes, L7Y3Cl2 [L = N-(2-methylquinolin-8-yl)-p-R-benzamides, 1: R = H; 2: R = OMe; 3: R = Me; 4: R = Cl], has been synthesized by the stoichiometric reaction of YCl3(THF)2 with the corresponding potassium amidates. All complexes have been characterized by elemental analysis and NMR spectroscopy. The molecular structure of complex 1 bearing seven amidate ligands was confirmed by single-crystal X-ray diffraction. Screening of these complexes, in the presence of BnOH, for ring-opening polymerization of caprolactone (ε-CL) revealed effective activities.

  通过 YCl3(THF)2 与相应酰胺酸钾的化学反应，合成了一系列三金属钇配合物 L7Y3Cl2 [L = N-(2-甲基喹啉-8-基)-p-R-苯甲酰胺，1：R = H；2：R = OMe；3：R = Me；4：R = Cl]。所有络合物都通过元素分析和核磁共振光谱进行了表征。单晶 X 射线衍射证实了含有七个酰胺配体的复合物 1 的分子结构。在有 BnOH 存在的情况下，对这些配合物进行筛选，发现它们对己内酰胺（δ-CL）的开环聚合具有有效的活性。
• 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.
• Syntheses, Characterization, and Ethylene (Co-)Polymerization Screening of Amidate Half-Titanocene Dichlorides
  作者：Shaofeng Liu、Wen-Hua Sun、Yanning Zeng、Deligeer Wang、Wenjuan Zhang、Yan Li

  DOI：10.1021/om1000748

  日期：2010.6.14

  A series of amidate half-titanocene dichlorides, Cp/TiLCl(2) [Cp' = Cp (as eta(5)-C(5)H(5)) or Cp* (as eta(5)-C(5)Me(5)), L = N-(2-methylquinolin-8-yl)-p-R-benzamides; C1: Cp' = Cp, R = OMe; C2: Cp' = Cp, R = Me; C3: Cp' = Cp, R = H; C4: Cp' = Cp, R = F; C5: Cp' = Cp, R = Cl; C6: Cp' = Cp*, R = OMe; C7: Cp' = Cp*, R = Me], have been synthesized by the stoichiometric reaction of Cp'TiCl(3) with the corresponding potassium amidates. All complexes are fully characterized by elemental and NMR analyses. The molecular structures of complexes C2 and C4 are confirmed by single-crystal X-ray diffraction, and the amidate moieties coordinate the titanium center by imino and alkoxide groups. The systems C1-C7/MAO show much higher activities toward ethylene polymerization than CpTiCl(3)/MAO or Cp*TiCl(3)/MAO systems. The procatalysts (C6 and C7) bearing a Cp* ligand exhibit higher activities than their analogues (C1-C5) containing a Cp ligand, while the amidate ligands containing electron-donating groups positively affect the catalytic behavior. Both increasing the ratio of MAO to titanium and reducing reaction temperature enhance the productivities; however, the molecular weights of the resultant polymers decrease with higher activities. Moreover, the C6/MAO system performs with high activity in the copolymerization of ethylene and 1-hexene or 1-octene.
• Regio- and Chemoselective Mono- and Bisnitration of 8-Amino quinoline Amides with Fe(NO₃)₃·9H₂O as Promoter and Nitro Source
  作者：Yan He、Ningning Zhao、Liqi Qiu、Xinying Zhang、Xuesen Fan

  DOI：10.1021/acs.orglett.6b02998

  日期：2016.12.2

  An efficient and regioselective remote C(5)–H nitration of 8-aminoquinoline amides by using the economical and nontoxic Fe(NO3)3·9H2O as promoter and nitro source has been developed. Furthermore, when CuCl2·2H2O was used as a catalyst, 8-aminoquinoline amides dominantly underwent bisnitration to give 5,7-dinitro-8-aminoquinoline amides. Notably, this is the first example in which Fe(NO3)3·9H2O plays

  通过使用经济，无毒的Fe（NO 3）3 ·9H 2 O作为促进剂和硝基源，开发了一种高效且区域选择性的8-氨基喹啉酰胺远程C（5）–H硝化方法。此外，当使用CuCl 2 ·2H 2 O作为催化剂时，主要将8-氨基喹啉酰胺进行双硝化以得到5,7-二硝基-8-氨基喹啉酰胺。值得注意的是，这是第一个例子，其中Fe（NO 3）3 ·9H 2 O既起螯合促进剂又起硝化剂的双重作用，而CuCl 2 ·2H 2 O则起喹啉双硝化的有效催化剂的作用。
• 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。