(E)-1-(4-chlorophenyl)-2-(4-methoxyphenyl)diazene | 21650-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: (E)-1-(4-chlorophenyl)-2-(4-methoxyphenyl)diazene
• 英文别名: trans-4-chloro-4'-methoxyazobenzene
• CAS: 21650-60-2
• 化学式: C₁₃H₁₁ClN₂O
• 分子量: 246.696
• InChiKey: QMQOBXQDTKWUBW-FOCLMDBBSA-N

物化性质

• 沸点：
  379.7±22.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.95
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-chlorophenyl)-2-(4-methoxyphenyl)diazene 在 [2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 氘代二甲亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.5h， 生成 4-(4-((4-methoxyphenyl)diazenyl)phenyl)-3-oxo-N-(2-oxotetrahydrofuran-3-yl)butanamide
  参考文献：
  名称：

  Easily Accessible, Highly Potent, Photocontrolled Modulators of Bacterial Communication

  摘要：

  External control of bacterial communication quorum sensing allows for the regulation of a multitude of biological processes. Herein, we describe the development of a new synthetic methodology, as well as the characterization, photoisomerization, and biological evaluation of a privileged series of novel photoswitchable quorum-sensing agonists and antagonists. The presented method allows for the rapid and convenient synthesis of previously unknown photoswitchable agonists with up to 70% quorum-sensing induction and inhibitors reaching up to 40% inhibition, which significantly extends the level of photocontrol over bacterial communication achieved before, Remarkably, for the lead photoswitchable agonist, a >700-fold difference in activity was observed between the irradiated and non-irradiated forms, which allows for antagonismto-agonism switching upon exposure to light, showing levels of control unprecedented in photopharmacology, Finally, utilizing this system, we were able to regulate toxin production in Pseudomonas aeruginosa with light.

  DOI：

  10.1016/j.chempr.2019.03.005
• 作为产物：
  描述：

  4-氯-偶氮苯 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 (E)-1-(4-chlorophenyl)-2-(4-methoxyphenyl)diazene
  参考文献：
  名称：

  偶氮染料：旧模板上新的钯和铜催化的偶联反应

  摘要：

  纪念穆罕默德·拉希德·谢赫（Muhammad Rashid Sheikh） 抽象的 据报道，使用多种过渡金属催化的反应（Stille，Heck，Ullmann和Suzuki偶联）对偶氮染料进行了精制。该方法学已被用于功能化香豆素偶氮染料共轭物的合成，这些底物可能在新传感器的开发中具有潜在的应用。 据报道，使用多种过渡金属催化的反应（Stille，Heck，Ullmann和Suzuki偶联）对偶氮染料进行了精制。该方法学已被用于功能化香豆素偶氮染料共轭物的合成，这些底物可能在新传感器的开发中具有潜在的应用。

  DOI：

  10.1055/s-0036-1591571

文献信息

• First use of p-tert-butylcalix[4]arene-tetra-O-acetate as a nanoreactor having tunable selectivity towards cross azo-compounds by trapping silver ions
  作者：Piyali Sarkar、Chhanda Mukhopadhyay

  DOI：10.1039/c5gc01859e

  日期：——

  p-tert-Butylcalix[4]arene-tetra-O-acetate was established for the first time as a member of the nanoreactor series, even without having any –OH group.

  p-tert-Butylcalix[4]arene-tetra-O-acetate首次被确定为纳米反应器系列的一员，即使没有任何-OH基团。

• Phenyliodine(III) Diacetate (PIDA) Mediated Synthesis of Aromatic Azo Compounds through Oxidative Dehydrogenative Coupling of Anilines: Scope and Mechanism
  作者：Kamarul Monir、Monoranjan Ghosh、Subhajit Mishra、Adinath Majee、Alakananda Hajra

  DOI：10.1002/ejoc.201301209

  日期：2014.2

  An efficient and environmentally benign method has been developed for the synthesis of symmetrical and unsymmetrical aromatic azo compounds through phenyliodine(III) diacetate (PIDA) mediated oxidative dehydrogenative coupling of anilines in high yields. The scope of the reaction is broad for both homo- and cross-dimerization. A plausible reaction mechanism has been proposed based on a structurally

  已经开发了一种高效且环境友好的方法，用于通过二乙酸苯碘 (III) (PIDA) 介导的苯胺氧化脱氢偶联以高产率合成对称和不对称的芳香偶氮化合物。该反应的范围对于均二聚和交叉二聚都很宽泛。基于结构特征的关键中间体提出了一种合理的反应机制，表明乙醇参与了反应途径。快速反应、无金属条件和官能团耐受性是这种方法的优点。
• Influence of the environment on kinetics and electronic structure of asymmetric azobenzene derivatives — experiment and quantum-chemical calculations
  作者：K Matczyszyn、W Bartkowiak、J Leszczynski

  DOI：10.1016/s0022-2860(01)00457-4

  日期：2001.5

  Abstract The kinetics of thermally driven cis – trans isomerisation of asymmetrically substituted azobenzenes dissolved in solvents of various polarities was measured spectrophotometrically. The solvatochromic effect was observed in 4-nitro-4′-aminoazobenzene as well as in 4-nitro-4′methoxyazobenzene. The experiment has been supplemented with quantum-chemical calculations. The solvent effect was taken

  摘要 用分光光度法测量了溶解在各种极性溶剂中的不对称取代偶氮苯的热驱动顺反异构化动力学。在 4-硝基-4'-氨基偶氮苯和 4-硝基-4'甲氧基偶氮苯中观察到溶剂化变色效应。该实验补充了量子化学计算。使用量子力学朗之万偶极子/蒙特卡罗 (QM/LD/MC) 方法考虑了溶剂效应。已在状态总和 (SOS) 方法中计算了所研究分子的一阶超极化张量。这两种方法都在全价方法 GRINDOL 中实现。
• Zr(OH) ₄ ‐Catalyzed Controllable Selective Oxidation of Anilines to Azoxybenzenes, Azobenzenes and Nitrosobenzenes
  作者：Jiaheng Qin、Yu Long、Fangkun Sun、Pan‐Pan Zhou、Wei David Wang、Nan Luo、Jiantai Ma

  DOI：10.1002/anie.202112907

  日期：2022.1.10

  Zr(OH)4 can catalyze the selective oxidation of anilines to azoxybenzenes, symmetric/unsymmetric azobenzenes and nitrosobenzenes for a wide range of substrates. Control experiments and DFT calculations reveal that the activation of H2O2 and O2 can be attributed to the bridging hydroxyl and terminal hydroxyl groups of Zr(OH)4, respectively.

  Zr(OH) 4可以催化苯胺选择性氧化为偶氮苯、对称/不对称偶氮苯和亚硝基苯，适用于多种底物。对照实验和 DFT 计算表明，H 2 O 2和 O 2的活化可分别归因于 Zr(OH) 4的桥接羟基和末端羟基。
• The selective synthesis of <i>N</i>-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents
  作者：Po-Yi Chen、Chi-Wei Hsu、Tong-Ing Ho、Jinn-Hsuan Ho

  DOI：10.1039/d0ra10068d

  日期：——

  The solvent-controllable photoreaction of 4-methoxyazobenzenes to afford 1-aryl-1H-benzimidazoles or N-arylbenzene-1,2-diamines has been studied. The irradiation of 4-methoxyazobenzenes in DMF containing 0.5 M hydrochloric acid provided N 2-aryl-4-methoxybenzene-1,2-diamines as the major product, while irradiation in acetal containing 0.16 M hydrochloric acid led to 1-aryl-6-methoxy-2-methyl-1H-benzimidazoles

  研究了 4-甲氧基偶氮苯的溶剂可控光反应得到 1-芳基-1H-苯并咪唑或 N-芳基苯-1,2-二胺。4-甲氧基偶氮苯在含有 0.5 M 盐酸的 DMF 中辐照产生 N 2-aryl-4-methoxybenzo-1,2-diamines 作为主要产物，而在含有 0.16 M 盐酸的乙缩醛中辐照产生 1-aryl-6-主要产品为甲氧基-2-甲基-1H-苯并咪唑。还讨论了解释选择性的可能反应机制。