2-chlorobenzylidene-2,6-diisopropylphenylamine | 780786-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chlorobenzylidene-2,6-diisopropylphenylamine
• 英文别名: 1-(2-chlorophenyl)-N-[2,6-di(propan-2-yl)phenyl]methanimine
• CAS: 780786-31-4
• 化学式: C₁₉H₂₂ClN
• 分子量: 299.843
• InChiKey: NMKFNWLPTQCEDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chlorobenzylidene-2,6-diisopropylphenylamine 在 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 生成 [PdCl(triphenylphosphine)(2-chlorobenzylidene-2,6-diisopropylphenylamine(-1H))]
  参考文献：
  名称：

  Cationic palladacycles as catalyst precursors for phenyl acetylene polymerization

  摘要：

  Novel cationic palladacycles based on benzylidene-2,6-diisopropylphenylimines were prepared via C-H activation using Pd(CH(3)CN)(2)Cl(2) as metal precursor. The complexes were fully characterized by IR and NMR spectroscopy, mass spectrometry and elemental analysis. The cationic palladacycles were found to be active catalysts for the polymerization of phenylacetylene producing largely trans-cisoidal PPA. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.07.044
• 作为产物：
  描述：

  2,6-二异丙基苯胺 、 2-氯苯甲醛 以 乙醇 为溶剂， 生成 2-chlorobenzylidene-2,6-diisopropylphenylamine
  参考文献：
  名称：

  通过镍催化的 C-Cl 键活化和芳基化引入 (2-CF3) 苯基

  摘要：

  描述了通过 C-Cl 键活化的简单和温和的催化芳基化。通过氯芳烃与有机锌试剂双(2-(三氟甲基)苯基)锌、四(三甲基膦)镍(0)之间的C,C-偶联反应，将含有2-三氟甲基的苯基引入到芳族亚胺分子中络合物作为有效的催化剂。在催化条件下，氯化苯甲亚胺被定量转化为预期的具有三氟甲基的苯甲亚胺。

  DOI：

  10.1002/zaac.201400609

文献信息

• Phenylacetylene polymerisation mediated by cationic cyclometallated palladium(<scp>ii</scp>) complexes bearing benzylidene 2,6-diisopropylphenylamine and its derivatives as ligands
  作者：M. Cassiem. Joseph、Andrew J. Swarts、Selwyn F. Mapolie

  DOI：10.1039/c8dt02728e

  日期：——

  A series of novel cationic palladacycle complexes bearing benzylidene-2,6-diisopropylphenylamine derivatives as ligands and with the general formula [Pd(MeCN)(L)(R-C6H3)CHN2,6-iPr2-C6H3}][B(3,5-(CF3)2-C6H3)] (R = H, Cl, Br, F, OMe and L = 1,3,5-triaza-7-phosphaadamantane (PTA), tricyclohexylphosphine (PCy3) and triphenylphosphine (PPh3)) were prepared and characterized by a range of analytical techniques

  一系列带有亚苄基-2,6-二异丙基苯基胺衍生物作为配体且通式为[Pd（MeCN）（L）（RC 6 H 3）CH N 2,6- i Pr 2 -C 6的新型阳离子palladacycle配合物H 3 }] [B（3,5-（CF 3）2 -C 6 H 3）]（R = H，Cl，Br，F，OMe和L = 1,3,5-triaza-7-phosphaadamantane（ PTA），三环己基膦（PCy 3）和三苯膦（PPh 3））的制备方法，并通过一系列分析技术进行了表征。发现这些阳离子的palladacycle配合物是用于苯乙炔聚合的活性预催化剂。该元的环金属化的环上的-取代被发现有关于该复合物，其包含吸电子取代基的催化剂的性能有显着影响，被认为是最活跃的在聚合过程。此外，增加膦配体的空间体积导致产生更高分子量的聚苯乙炔（PPA）。在25进行的聚合反应℃下，得到的两个的混合物CI S-TRAnsoidal和TRAN
• Preparation, characterization and evaluation of novel 1,3,5-triaza-7-phosphaadamantane (PTA)-based palladacycles as anti-cancer agents
  作者：A. Blanckenberg、S. Aliwaini、S.W. Kimani、A. van Niekerk、A. Neumann-Mufweba、S. Prince、S.F. Mapolie

  DOI：10.1016/j.jorganchem.2017.09.005

  日期：2017.11

  A series of novel mononuclear 1,3,5-triaza-7-phosphaadamantane (PTA)-based palladacycles were prepared by cleaving m-Cl binuclear orthopalladated dimers of substituted benzylidene-2,6-diisopropylphenylamines. All complexes were fully characterized using IR and NMR spectroscopy, mass spectrometry as well as elemental analysis. In-vitro evaluation of the complexes as anti-cancer agents against the breast-cancer cell lines MCF7 and MDA-MB 231 as well the melanoma cell line ME1402 shows that four of the five complexes tested are active. These palladacycles exhibit their cytotoxicity by inducing DNA damage which subsequently triggers apoptosis. DNA binding studies using electrophoresis and spectroscopic techniques, such as UV-Vis and circular dichroism spectroscopy, confirms that the palladacycle, C2 definitely interacts with DNA. Results from these DNA binding experiments seem to rule out co-valent and intercalative binding, pointing rather to a non-covalent interaction, with electrostatic binding being the most likely possibility. It is envisioned that this would probably involve a hydrolysed or solvated derivative of C2. (C) 2017 Elsevier B.V. All rights reserved.