C6H4(Me)CHNC6H3(iPr)2

• 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: C6H4(Me)CHNC6H3(iPr)2
• 英文别名: N-[2,6-di(propan-2-yl)phenyl]-1-(2-methylphenyl)methanimine
• 化学式: C₂₀H₂₅N
• 分子量: 279.425
• InChiKey: BHCDYYHFMUYVKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  双(乙腈)氯化钯(II) 、 C6H4(Me)CHNC6H3(iPr)2 在 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以56%的产率得到
  参考文献：
  名称：

  Preparation, characterization and evaluation of novel 1,3,5-triaza-7-phosphaadamantane (PTA)-based palladacycles as anti-cancer agents

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2017.09.005
• 作为产物：
  描述：

  2,6-二异丙基苯胺 、 2-甲基苯甲醛 在 5% sulfaneted anatase-titania (TiO₂-SO₄^-2) 作用下， 以 neat (no solvent) 为溶剂， 反应 0.67h， 以82%的产率得到C6H4(Me)CHNC6H3(iPr)2
  参考文献：
  名称：

  Kumar; Krishnakumar; Sobral, Abilio J.F.N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, p. 1231 - 1238

  摘要：

  DOI：

文献信息

• Palladium(II)-Catalyzed CH Bond Arylation of Electron-Deficient Arenes at Room Temperature
  作者：Matthew J. Tredwell、Moises Gulias、Nadine Gaunt Bremeyer、Carin C. C. Johansson、Beatrice S. L. Collins、Matthew J. Gaunt

  DOI：10.1002/anie.201005990

  日期：2011.2.1

  Mild and tolerant: A novel PdII‐catalyzed CH bond arylation with aryl‐BF3K salts transforms various electron‐deficient arenes under mild reaction conditions. Benzaldehydes are functionalized in the ortho position using a temporary imine directing group that controls the cyclopalladation. A broad range of benzaldimines are compatible with this process (see scheme).

  轻度和宽容：一种新颖的钯II催化的Ç  H键与芳基化芳基- BF 3个温和反应条件下钾盐变换各种缺电子芳烃。使用控制环palpalladation的临时亚胺导向基团在邻位将苯甲醛官能化。各种各样的苯扎二胺与此工艺兼容（请参阅方案）。
• Kumar; Krishnakumar; Sobral, Abiiio J. F. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 10, p. 1231 - 1238
  作者：Kumar、Krishnakumar、Sobral, Abiiio J. F. N.、Subash、Swaminathan、Sankaran

  DOI：——

  日期：——
• Kumar; Krishnakumar; Sobral, Abilio J.F.N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, p. 1231 - 1238
  作者：Kumar、Krishnakumar、Sobral, Abilio J.F.N.、Subash、Swaminathan、Sankaran

  DOI：——

  日期：——
• 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.