1,4‑di(4‑methylphenyl)‑1,4‑diaza‑2,3‑methyl‑1,3‑butadiene | 19215-50-0

• 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: 1,4‑di(4‑methylphenyl)‑1,4‑diaza‑2,3‑methyl‑1,3‑butadiene
• 英文别名: N-(3-(4-methylphenylimino)butan-2-ylidene)-4-methylbenzenamine；1,4-Bis(4-methylphenyl)-2,3-dimethyl-1,4-diazabutadien；butane-2,3-dione-bis-p-tolylimine；Butan-2,3-dion-bis-p-tolylimin；2,3-Me2-p-tolilDAB；Diacetyl-bis(4-methyl-anil)；2,3-Butanediimine, N,N'-bis(4-methylphenyl)-；2-N,3-N-bis(4-methylphenyl)butane-2,3-diimine
• CAS: 19215-50-0
• 化学式: C₁₈H₂₀N₂
• 分子量: 264.37
• InChiKey: FHELVLYESJUGRR-UHFFFAOYSA-N

物化性质

• 熔点：
  110.2-111.6 °C
• 沸点：
  407.3±48.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4‑di(4‑methylphenyl)‑1,4‑diaza‑2,3‑methyl‑1,3‑butadiene 在 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以67%的产率得到N-(3-(2-chloro-4-methylphenylimino)butan-2-ylidene)-2-chloro-4-methylbenzenamine
  参考文献：
  名称：

  Potassium Tellurocyanate Mediated Coupling Reactions ofN-(1-Chloroethylidene)Arylamines

  摘要：

  The reaction of potassium tellurocyanate (prepared in situ) with N-(1-chloroethylidene)arylamines (i.e., 4-RC6H4N = C(CH3)Cl, where R = H, Cl, CH3 and NO2) in DMSO solution gave unexpectedly, after hydrolysis, the corresponding N-(3-(arylamino)butan-2-ylidene)arylamines in 63-78%. Reaction of N-(3-(arylamino)butan-2-ylidene)arylamines with SOCl2 or with Br-2 resulted in the substitution of a halogen on the aromatic rings. The presence of a water molecule within the structure of the synthesized diimines was rationalized theoretically by Density Functional Theory (DFT). All compounds were characterized by elemental analysis, IR, NMR and mass spectroscopic data.

  DOI：

  10.1080/10426507.2014.902830
• 作为产物：
  描述：

  N-(1-chloroethylidene)-4-methylbenzenamine 在 potassium tellurocyanate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.5h， 以76%的产率得到1,4‑di(4‑methylphenyl)‑1,4‑diaza‑2,3‑methyl‑1,3‑butadiene
  参考文献：
  名称：

  Potassium Tellurocyanate Mediated Coupling Reactions ofN-(1-Chloroethylidene)Arylamines

  摘要：

  The reaction of potassium tellurocyanate (prepared in situ) with N-(1-chloroethylidene)arylamines (i.e., 4-RC6H4N = C(CH3)Cl, where R = H, Cl, CH3 and NO2) in DMSO solution gave unexpectedly, after hydrolysis, the corresponding N-(3-(arylamino)butan-2-ylidene)arylamines in 63-78%. Reaction of N-(3-(arylamino)butan-2-ylidene)arylamines with SOCl2 or with Br-2 resulted in the substitution of a halogen on the aromatic rings. The presence of a water molecule within the structure of the synthesized diimines was rationalized theoretically by Density Functional Theory (DFT). All compounds were characterized by elemental analysis, IR, NMR and mass spectroscopic data.

  DOI：

  10.1080/10426507.2014.902830

文献信息

• Lysosome-targeted potent half-sandwich iridium(III) α-diimine antitumor complexes
  作者：Deliang Kong、Lihua Guo、Meng Tian、Shumiao Zhang、Zhenzhen Tian、Huayun Yang、Ye Tian、Zhe Liu

  DOI：10.1002/aoc.4633

  日期：2019.1

  F6 (Cpx = Cp*, tetramethyl(phenyl)cyclopentadienyl (Cpxph) or tetramethyl(biphenyl)cyclopentadienyl (Cpxbiph); N^N = diamine) have been synthesized and characterized. The molecular structure of 1A was determined using single‐crystal X‐ray diffraction analysis. The hydrolysis of 1A–5C was monitored using UV–visible spectra. Complexes 3A–3C showed catalytic activity for the oxidation of NADH to NAD+

  十五有机金属铱（III）半夹心络合物（1A - 5C）具有通式[（η 5 -Cp X）IR（N ^ N）CL] PF 6（CP X =的Cp *，四甲基（苯基）环戊二烯基（已经合成并表征了Cp xph）或四甲基（联苯）环戊二烯基（Cp xbiph； N ^ N =二胺）。1A的分子结构使用单晶X射线衍射分析确定。1A – 5C的水解使用紫外可见光谱进行监测。配合物3A – 3C显示出将NADH氧化为NAD的催化活性+，其中3C在450分钟内显示最高的29.9营业额。在药物治疗24或48小时后，针对两种人类癌细胞系（HeLa和A549）进行了MTT分析的细胞毒性检查。该复合物显示出高效能，其中最有效的复合物（3C； IC 50  = 3.4μM）在暴露24小时后对A549细胞的活性是顺铂的六倍。随着Cp环上的苯基取代，对A549细胞的细胞毒性作用增强：Cp xbiph > Cp xph > Cp
• [EN] COMPOSITIONS COMPRISING ORGANOMETALLIC MOLYBDENUM COMPOUNDS FOR TREATING CANCER<br/>[FR] COMPOSITIONS COMPRENANT DES COMPOSES DE MOLYBDENE ORGANOMETALLIQUES POUR LE TRAITEMENT DU CANCER
  申请人：IBET INST DE BIOLOG EX E TECNO

  公开号：WO2005087783A1

  公开（公告）日：2005-09-22

  The invention provides several molybdenum (II) complexes (see classes I and II, figure 1) as well as pharmaceutical compositions comprising these compounds, that are useful for treating cancer and describes synthetic methods and intermediates useful for preparing the compounds.

  该发明提供了几种钼（II）配合物（见I类和II类，图1），以及包括这些化合物的药物组合物，用于治疗癌症，并描述了用于制备这些化合物的合成方法和中间体。
• One‐Step Access to Heteroatom‐Functionalized Imidazol(in)ium Salts
  作者：Dmitry V. Pasyukov、Maxim A. Shevchenko、Konstantin E. Shepelenko、Oleg V. Khazipov、Julia V. Burykina、Evgeniy G. Gordeev、Mikhail E. Minyaev、Victor M. Chernyshev、Valentine P. Ananikov

  DOI：10.1002/anie.202116131

  日期：2022.2.21

  and imidazolinium salts in one step via cascade reactions of easily available 1,4-diaza-1,3-butadienes with trialkyl orthoformates and heteroatomic nucleophiles was developed. Feasibility of the new imidazol(in)ium salts for direct metallation to give M/NHC complexes (M=Pd, Ni, Cu, Ag, Au) was demonstrated.

  开发了一种通过容易获得的1,4-二氮杂-1,3-丁二烯与原甲酸三烷基酯和杂原子亲核试剂的级联反应一步合成多种杂原子官能化咪唑鎓和咪唑啉鎓盐的新策略。证明了新的咪唑（in）鎓盐直接金属化以产生 M/NHC 配合物（M=Pd、Ni、Cu、Ag、Au）的可行性。
• The hydroboration of α-diimines
  作者：Stephen J. Geier、Justin F. Binder、Christopher M. Vogels、Lara K. Watanabe、Charles L. B. Macdonald、Stephen A. Westcott

  DOI：10.1039/d1nj01025e

  日期：——

  The uncatalyzed addition of catecholborane to α-diimines has been examined. Reactions proceed smoothly at room temperature in the absence of a catalyst or additive, providing bis-hydroboration products with 3-coordinate boron centres or mono-hydroboration products with 4-coordinate boron centres, depending on the nature of the diimine reagent.

  已经研究了儿茶酚硼烷未催化添加到α-二亚胺中。反应在室温下在没有催化剂或添加剂的情况下平稳进行，根据二亚胺试剂的性质，可提供具有3坐标硼中心的双氢硼化产物或具有4坐标硼中心的单氢硼化产物。
• The formation of dinuclear trichloro-bridged and mononuclear ruthenium complexes from the reactions of dichlorotris(p-tolylphosphine)ruthenium(II) with diazabutadiene ligands
  作者：Meng Guan Tay、Ying Ying Chia、Suzie Hui Chin Kuan、Tze Pei Phan

  DOI：10.1007/s11243-018-00293-0

  日期：2019.4

  Meanwhile, two mononuclear Ru(II) complexes [RuCl2(P(p-tolyl)3)2(R-DAB)] were obtained from the reactions of the [RuCl2P(p-tolyl)3}] precursor with R-DAB ligands in THF. The two trans-mononuclear complexes were characterized by X-ray crystallography and solid-state 31P NMR. A temperature-dependent 31P NMR study was carried out to monitor the formation of dinuclear and mononuclear complexes.

  已经制备了具有二氮杂丁二烯 (R-DAB) 配体的 Ru(II) 配合物。RuCl3·nH2O 与 P(p-tolyl)3 反应得到 [RuCl2P(p-tolyl)3}] 前体，其与甲苯中的 R-DAB 反应得到双核三氯桥连 Ru(II) 配合物 [Ru2Cl3 (P(p-tolyl)3)2(R-DAB)2](BF4) 已通过光谱方法表征。此外，使用 X 射线晶体学表征了其中一种配合物。同时，由 [RuCl2P(p-tolyl)3}] 前驱体与 R-反应得到两个单核 Ru(II) 配合物 [RuCl2(P(p-tolyl)3)2(R-DAB)]。 THF 中的 DAB 配体。这两种反式单核配合物通过 X 射线晶体学和固态 31 P NMR 进行了表征。进行温度依赖性 31P NMR 研究以监测双核和单核复合物的形成。