N,N'-(1,4-phenylenebis(methan-1-yl-1-ylidene))bis(4-chloroaniline) | 904-70-1

• 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: N,N'-(1,4-phenylenebis(methan-1-yl-1-ylidene))bis(4-chloroaniline)
• 英文别名: 1,4-bis<(4-chlorophenyl)iminomethyl>benzene；terephthalaldehyde bis-(4-chloro-phenylimine)；Terephthalaldehyd-bis-(4-chlor-phenylimin)；N-(4-chlorophenyl)-1-[4-[(4-chlorophenyl)iminomethyl]phenyl]methanimine
• CAS: 904-70-1
• 化学式: C₂₀H₁₄Cl₂N₂
• 分子量: 353.251
• InChiKey: ITCBZDBGGMJBQB-UHFFFAOYSA-N

物化性质

• 沸点：
  513.4±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2921590090

反应信息

• 作为反应物：
  描述：

  N,N'-(1,4-phenylenebis(methan-1-yl-1-ylidene))bis(4-chloroaniline) 、 四氯苯醌 以 乙酸乙酯 为溶剂， 反应 72.0h， 生成 2,5-二(4-氯苯胺基)-3,6-二氯苯醌
  参考文献：
  名称：

  Aly; Hassan; Mohamed, Pharmazie, 1997, vol. 52, # 4, p. 282 - 287

  摘要：

  DOI：
• 作为产物：
  描述：

  对苯二甲醛 、 对氯苯胺 生成 N,N'-(1,4-phenylenebis(methan-1-yl-1-ylidene))bis(4-chloroaniline)
  参考文献：
  名称：

  Novel Reaction between 3,4,5,6-Tetrachloro-1,2-benzoquinone and Bis-azomethines

  摘要：

  3,4,5,6-四氯-1,2-苯醌（o-CHL）与N,N'-二环己基-1,2-乙二亚胺1a反应，形成了一种短暂的缩合产物，随后与另一分子1a发生[4 + 2]环加成反应。另一方面，利用N,N'-二芳基-1,2-乙二亚胺1b,c作为双烯亲和体，首先生成取代的o-CHL，然后与另一分子1b,c进行[4 + 2]环加成反应。在N,N'-二(烷基/芳基)-对-二亚苯1a—f与同一受体的反应中，观察到了类似的行为。

  DOI：

  10.1246/bcsj.69.2249

文献信息

• Exploration of imidazole and imidazopyridine dimers as anticancer agents: Design, synthesis, and structure–activity relationship study
  作者：Sangeetha Meenakshisundaram、Manoj Manickam、Thanigaimalai Pillaiyar

  DOI：10.1002/ardp.201900011

  日期：2019.12

  Dimerization of proteins/receptors plays a critical role in various cellular processes, including cell proliferation and differentiation. Therefore, targeting such dimeric proteins/receptors by dimeric small molecules could be a potential therapeutic approach to treating various diseases, including inflammation‐associated diseases like cancer. A novel series of bis‐imidazoles (13–18) and bis‐imidazo[1,2‐a]pyridines

  蛋白质/受体的二聚化在各种细胞过程中起着关键作用，包括细胞增殖和分化。因此，通过二聚体小分子靶向此类二聚体蛋白/受体可能是治疗各种疾病（包括癌症等炎症相关疾病）的潜在治疗方法。一系列新型双咪唑 (13-18) 和双咪唑并 [1,2-a] 吡啶 (19-28) 因具有抗癌活性而由席夫碱二聚体 (1-12) 设计和合成。筛选了所有合成的化合物对三种癌细胞系的抗癌活性，包括宫颈癌 (HeLa)、乳腺癌 (MDA-MB-231) 和肾癌 (ACHN)。从构效关系研究中，咪唑并[1,2-a]吡啶（19-28）显示出显着的细胞毒活性，化合物 19 和 24 显示出对所有三种细胞系的最佳抑制活性。特别是，19 和 24 对乳腺癌细胞系都非常有效（19，GI50 = 0.43 µM；24，GI50 = 0.3 µM），超过了对照阿霉素的活性（GI50 = 0.51 µM）。化合物 19 和 24 的体内抗
• Bis-imine-cyclometalated macrocycles: synthesis, characterization and observation of solution behaviour
  作者：Hao Li、Ying-Feng Han、Guo-Xin Jin

  DOI：10.1039/c0dt01377c

  日期：——

  A novel class of cyclometalated macrocycles [(Cp*Ir)2(R–NC–C6H2–CN–R)2]2(pyrazine)2·(OTf)4 [R = Ph (4a), p-MeOC6H4 (4b), p-MeC6H4 (4c), p-ClC6H4 (4d), Me (4e)]; [(Cp*Rh)2(R–NC–C6H2–CN–R)2]2(pyrazine)2·(OTf)4 [R = Ph (4a′), p-MeOC6H4 (4b′), p-MeC6H4 (4c′)] and [(Cp*Ir)2(R–CN–C6H4–NC–R)2]2(pyrazine)2·(OTf)4 [R = Ph (5a), p-MeOC6H4 (5b)] was stepwise constructed through the double-site C–H activation of aromatic bis-imine substrates. The structures of binuclear complexes and tetranuclear macrocycles were confirmed by single-crystal X-ray diffraction. Isomers were found both in binuclear species and macrocyclic complexes. Flexible substrates led to the existence of isomers for binuclear species, yet gave no isomers after macrocyclic constructions; rigid ones, in contrast, led to isomers only for macrocyclic species. The isomers of tetranuclear macrocycles were thermodynamically stable to reversible transformation on a scale of days. Robust bonding and a certain degree of rigidity were invoked to explain the existence of isomers. This is the first example, to our knowledge, in which coordinated macrocycles containing half-sandwich Cp*M (M = Ir, Rh) fragments have been constructed, without a dynamic reversible process.

  一类新型环金属化大环 \([(\textCp*}\textIr})_2(\textR–NC–C}_6\textH}_2\text–CN–R})_2] _2(\textpyrazine})_2·(\textOTf})_4\) \[R = \textPh (4a)}, \textp-MeOC}_6\textH}_4\text (4b)}, \textp-MeC}_6\textH}_4\text (4c)}, \textp-ClC}_6\textH}_4\text (4d)}, \textMe (4e)}\]; \([(\textCp*}\textRh})_2(\textR–NC–C}_6\textH}_2\text–CN–R})_2] _2(\textpyrazine})_2·(\textOTf})_4\) \[R = \textPh (4a′)}, \textp-MeOC}_6\textH}_4\text (4b′)}, \textp-MeC}_6\textH}_4\text (4c′)}\] 和 \([(\textCp*}\textIr})_2(\textR–CN–C}_6\textH}_4\text–NC–R})_2] _2(\textpyrazine})_2·(\textOTf})_4\) \[R = \textPh (5a)}, \textp-MeOC}_6\textH}_4\text (5b)}\] 通过对芳香双亚胺底物进行双位点C–H活化，逐步构建而成。双核配合物和大环结构的确认通过单晶X射线衍射完成。在双核物种和大环配合物中都发现了异构体。柔性底物导致双核物种存在异构体，但在大环构建后没有异构体；相反，刚性底物仅导致大环物种的异构体。四核大环异构体在几天的时间尺度上是热力学稳定的，可逆转变。引入强键合和一定程度的刚性来解释异构体的存在。据我们所知，这是首次在没有动态可逆过程的情况下构建含有半三明治Cp*M (M = Ir, Rh)片段的配位大环的例子。
• An extending evidence of molecular conformation on spectroscopic properties of symmetrical bis-Schiff bases
  作者：Zhengjun Fang、Chenzhong Cao、Jianfang Chen、Xingchen Deng

  DOI：10.1016/j.molstruc.2014.01.073

  日期：2014.4

  Abstract The relationship between the molecular conformation and spectroscopic properties of symmetrical bis-Schiff bases, was explored experimentally. The synthesis, crystal structures, and spectroscopic behaviors of symmetrical bis-Schiff bases derived from 1,4-Phthalaldehyde, p -Y C 6 H 4 N CHC 6 H 4 CH NC 6 H 4 p -Y (Y = OMe, Me, H, Cl, or F) were reported. The results show when the effect of distance

  摘要 通过实验研究了对称双席夫碱的分子构象与光谱性质之间的关系。衍生自 1,4-苯甲醛的对称双席夫碱的合成、晶体结构和光谱行为，p -YC 6 H 4 N CHC 6 H 4 CH NC 6 H 4 p -Y (Y = OMe, Me, H 、Cl 或 F)。结果表明，当考虑X或Y与亚胺碳之间距离的影响时，对称双席夫碱的υ max 或δ C (CN) 与取代基参数之间具有良好的相关性。相关结果表明，对于衍生自 1,4-苯二胺和 1,4-苯二醛的对称双席夫碱，紫外吸收光谱取决于苯胺环上的取代基和二面角 τ ，并且术语 sin( τ ) 适合修改取代对 υ max 的影响。然而，实验研究表明，二面角 τ 对 δ C (CN) 值的影响有限。这项研究提供了分子构象对对称双席夫碱光谱性质影响的扩展证据。
• Efficient formation of organoiridium macrocycles via C–H activation directed self-assembly
  作者：Ying-Feng Han、Hao Li、Lin-Hong Weng、Guo-Xin Jin

  DOI：10.1039/b923335k

  日期：——

  Versatile and efficient procedures for the construction and modification of organometallic macrocycles with half-sandwich Ir corners via C–H activation and self-assembly have been developed.

  通过C-H活化和自组装，已经开发出用于构建和修饰具有半三明治Ir角的有机金属大环的通用且高效的程序。
• Muzalewski, Feliks; Gawinecki, Ryszard, Polish Journal of Chemistry, 1981, vol. 55, # 3, p. 565 - 572
  作者：Muzalewski, Feliks、Gawinecki, Ryszard

  DOI：——

  日期：——