N,N'-bis(8-quinolyl)-2,2-dimethylmalonamide

• 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,N'-bis(8-quinolyl)-2,2-dimethylmalonamide
• 英文别名: 2,2-dimethyl-N,N'-di(quinolin-8-yl)propanediamide
• 化学式: C₂₃H₂₀N₄O₂
• 分子量: 384.437
• InChiKey: MGBBUWCWGHTMKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis(8-quinolyl)-2,2-dimethylmalonamide 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Bio-inspired Cu(ii) amido-quinoline complexes as catalysts for aromatic C–H bond hydroxylation

  摘要：

  Cu(ii)-tetradentate 氨基喹啉配合物在没有外部碱的情况下，以 H2O2 为氧化剂，通过非自由基途径（TON ≥720）有效催化了芳香族 C-H 羟基化反应，对酚的选择性高达约 90%。

  DOI：

  10.1039/d2dt03242b
• 作为产物：
  描述：

  二甲基丙二酸二乙酯 在 吡啶 、 草酰氯 、 sodium hydroxide 作用下， 以 乙醇 、 苯 为溶剂， 反应 18.0h， 生成 N,N'-bis(8-quinolyl)-2,2-dimethylmalonamide
  参考文献：
  名称：

  Design of bisquinolinyl malonamides as Zn2+ ion-selective fluoroionophores based on the substituent effect

  摘要：

  A series of malonamides possessing two quinoline moieties were synthesized and characterized as fluoroionophores for the Zn2+ ion. We focused on the relationship between the substituents introduced to the C2-position of the malonamides and their Zn2+ ion-selectivity, exploiting the structural effect of the substituents in the design of the fluoroionophores with high selectivity. The substituents introduced to the malonamides were the methyl, benzyl and naphthalenylmethyl groups. In dimethyl sulfoxide solvent, all substituted bisquinolinyl malonamides showed excellent fluorescence sensing for the Zn2+ ion, while unsubstituted bisquinolinyl malonamide 1 displayed ratiometric sensing for the Co2+ ion. N,N'-Bis(8-quinolyI)-2-methyl-2-naphthalenylmethyl malonamide 4 exhibited the highest Zn2+ ion-selectivity against the Cd2+ ion. Although the substituents introduced into the C2-position are spatially distant from the quinoline recognition moiety, this study indicated that they greatly influenced the ion selectivities of the bisquinolinyl malonamides. Furthermore, it was demonstrated that visible fluorescence analyses could be performed on malonamide 4. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.11.016

文献信息

• C–H bond chlorination using nickel(<scp>ii</scp>) complexes of tetradentate amido-quinoline ligands
  作者：Sanjay Adhikari、Aniruddha Sarkar、Basab Bijayi Dhar

  DOI：10.1039/d2cc00639a

  日期：——

  Ni(II)-tetradentate amido-quinoline complexes effectively catalysed C–H chlorination of a series of hydrocarbons in the presence of NaOCl and acetic acid. The bond dissociation energy of the C(sp3)–H bond of the substrates varies from 99.3 kcal mol−1 (cyclohexane) to 87 kcal mol−1 (ethyl benzene). Exclusively chlorinated products (TON: 220 for cyclohexane) were obtained without any hydroxylated products

  Ni( II )-四齿酰胺-喹啉配合物在 NaOCl 和乙酸存在下有效催化一系列烃的 C-H 氯化反应。底物的C(sp 3 )-H键的键解离能从99.3 kcal mol -1 (环己烷)到87 kcal mol -1 (乙苯)不等。获得了没有任何羟基化产物的完全氯化产物（环己烷的 TON：220），从而模拟了卤化酶的活性。