N-(4-chlorophenyl)-N'-(picolinylidene)-hydrazine | 119259-99-3

• 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-(4-chlorophenyl)-N'-(picolinylidene)-hydrazine
• 英文别名: pyridine-2-carboxaldehyde-4-chlorobenzoylhydrazone；2-pyridinecarboxaldehyde-p-chlorobenzoylhydrazone；2-formylpyridine-para-chlorophenyl hydrazone；N-(C6H4ClCO)-N'-(picolinylidene)hydrazine；4-chloro-N-(pyridin-2-ylmethylideneamino)benzamide
• CAS: 119259-99-3
• 化学式: C₁₃H₁₀ClN₃O
• mdl: MFCD00434648
• 分子量: 259.695
• InChiKey: OSEOOXCLAYRSPE-UHFFFAOYSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)-N'-(picolinylidene)-hydrazine 在 碘 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以66%的产率得到2-(4-chlorophenyl)-5-(pyridin-2-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Preparation and Acetylcholinesterase Inhibitory Activities of Pyridine-Based 1,3,4-Oxadiazole Derivatives

  摘要：

  DOI：

  10.3987/com-20-14266
• 作为产物：
  描述：

  吡啶-2-甲醛 、 4-氯苯甲酰肼 在 甲酸 作用下， 以 二甲基亚砜 为溶剂， 生成 N-(4-chlorophenyl)-N'-(picolinylidene)-hydrazine
  参考文献：
  名称：

  Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor

  摘要：

  A systematically generated series of hydrazones were analyzed as potential inhibitors of anthrax lethal factor. The hydrazones were screened using one UV-based and two fluorescence-based in vitro assays. The study identified several inhibitors with IC50 values in the micromolar range, and importantly, significant differences in the types of inhibition were observed with the different assays. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2006.07.004

文献信息

• Synthesis, structure and catalytic applications of octahedral nickel(II) benzoylhydrazone complex: Suzuki–Miyaura cross-coupling reaction of aryl bromides with arylboronic acid
  作者：Pandimuni Kalpaga Suganthy、Rupesh Narayana Prabhu、Venugopal Shanmugham Sridevi

  DOI：10.1016/j.ica.2016.05.015

  日期：2016.8

  Abstract A simple route for the synthesis of a new octahedral nickel(II) complex (1) containing 4-chloro-benzoic acid pyridin-2-ylmethylene-hydrazide ligand (HL, where H represents the dissociable proton) has been described. The characterization of the complex having the formula [Ni(μ3-O,N,N-L)2] has been established by elemental analysis, ESI-MS, spectral methods and single crystal X-ray crystallography

  摘要描述了一种简单的合成新的八面体镍（II）配合物的方法，该配合物包含4-氯-苯甲酸吡啶-2-基亚甲基-酰肼配体（HL，其中H表示可解离的质子）。已通过元素分析，ESI-MS，光谱方法和单晶X射线晶体学建立了具有式[Ni（μ3-O，N，NL）2]的配合物的表征。此外，在溶剂，碱和催化剂负载的优化条件下，发现新的络合物可作为取代的芳基溴化物（单溴化物和二溴化物）与各种具有不同电子效应的芳基硼酸的Suzuki-Miyaura反应的活性均相催化剂。联苯和三苯衍生物的分离产率中等至优异。
• Ruthenium(ii) complexes containing RuN4O2 spheres assembled via pyridine-imine-amide coordination. Syntheses, structures, properties and protonation behaviour of coordinated amide
  作者：Satyanarayan Pal、Samudranil Pal

  DOI：10.1039/b110912j

  日期：2002.4.26

  A series of ruthenium(II) complexes of general formula [RuL2] with the pyridine-N, the imine-N and the amide-O donor N-(aroyl)-N′-(picolinylidene)hydrazines (HL) has been synthesized. The ligands differ on the substituent at the para position of the aroyl fragment. The complexes have been characterized by analytical, 1H NMR, electronic absorption spectroscopy and cyclic voltammetry. X-Ray structures of representative complexes have been determined. The lowest energy MLCT (Ru(dπ) → L(π*)) transitions for these complexes are observed at essentially identical wavelength (544 ± 1 nm). The complexes display a metal centred oxidation and a ligand centred reduction in the potential ranges 0.44 to 0.59 V and −1.49 to −1.35 V (vs. Ag/AgCl), respectively. The differences in the metal and ligand redox potentials (ΔE1/2) are practically same (1.94 ± 0.01 V) for all the complexes. The identical MLCT band positions and the same ΔE1/2 values suggest that in this series of complexes, the energy gap between the metal-dπ and the ligand-π* levels is constant. The effective pKa values of the species obtained by protonation of the coordinated amide functionalities in one of the complexes have been evaluated by spectrophotometric titration. The corresponding diprotonated species has been characterized by X-ray crystallography.

  我们合成了一系列通式为[RuL2]的钌(II)配合物，它们具有吡啶-N、亚胺-N 和酰胺-O 供体 N-（酰基）-N′-（偏吡啶基）肼（HL）。这些配体在芳基片段对位的取代基上有所不同。这些配合物通过分析、1H NMR、电子吸收光谱和循环伏安法进行了表征。代表性复合物的 X 射线结构已经确定。这些配合物的最低能量 MLCT（Ru(dπ) → L(π*)）转变的波长（544 ± 1 nm）基本相同。在 0.44 至 0.59 V 和 -1.49 至 -1.35 V（相对于 Ag/AgCl）的电位范围内，这些配合物分别显示出以金属为中心的氧化和以配体为中心的还原。所有配合物的金属和配体氧化还原电位（ΔE1/2）几乎相同（1.94 ± 0.01 V）。相同的 MLCT 带位置和相同的 ΔE1/2 值表明，在这一系列配合物中，金属-π 级和配体-π* 级之间的能隙是恒定的。通过分光光度滴定法评估了其中一个配合物中配位酰胺官能团质子化后得到的物种的有效 pKa 值。相应的二质子化物种已通过 X 射线晶体学进行了表征。
• Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor
  作者：M. Leslie Hanna、Theodore M. Tarasow、Julie Perkins

  DOI：10.1016/j.bioorg.2006.07.004

  日期：2007.2

  A systematically generated series of hydrazones were analyzed as potential inhibitors of anthrax lethal factor. The hydrazones were screened using one UV-based and two fluorescence-based in vitro assays. The study identified several inhibitors with IC50 values in the micromolar range, and importantly, significant differences in the types of inhibition were observed with the different assays. (c) 2006 Elsevier Inc. All rights reserved.
• Some trans-chlorobis(triphenylphosphine)ruthenium(II) complexes with N,N,O-donor N-(aroyl)-N′-(picolinylidene)hydrazines
  作者：Raji Raveendran、Samudranil Pal

  DOI：10.1016/j.poly.2004.09.027

  日期：2005.1

  The reactions of [Ru(PPh3)(3)Cl-2] and N-(aroyl)-N'-(picolinylidene)hydrazines (HL): derived from 2-pyridinecarbaldehyde and 4-substituted aroylhydrazines in boiling methanol provide mixed-ligand complexes having the general formula trans-[RuL(PPh3)(2)Cl]. The complexes were characterized by analytical, spectroscopic and electrochemical measurements. The +2 oxidation state of the metal ions in these complexes is confirmed by their diamagnetic nature in the solid state and electrically non-conducting behavior in solution. The X-ray structure of a representative complex has been determined. The metal ion is in a distorted octahedral N2OP2Cl coordination sphere. The monoanionic pyridine-N. imine-N and deprotonated amide-O donor ligand and the chlorine atom form an N2OCl square-plane around the metal centre and the P-atoms of the PPh3 Molecules OCCUPY the remaining two axial sites. The P-31 NMR spectra of all the complexes in CDCl3 solutions are consistent with the irons orientation of the PPh3 molecules. Electronic spectra of the complexes in dichloromethane solution display several bands in the range 590-261 nm due to metal-to-ligand charge transfer and intraligand transitions. Cyclic voltammograms of the complexes in dimethylformamide solution display the reversible Ru(III)/Ru(II) couple in the potential range 0.40-0.52 V (versus saturated calomel electrode). The trend in these potential values reflects the polar effect of the substituents on the aroyl moiety of the ligand (L-). (C) 2004 Elsevier Ltd. All rights reserved.
• Dynamic Acylhydrazone Metal Ion Complex Libraries: A Mixed–Ligand Approach to Increased Selectivity in Extraction
  作者：Seema Choudhary、Janet R. Morrow

  DOI：10.1002/1521-3773(20021104)41:21<4096::aid-anie4096>3.0.co;2-0

  日期：2002.11.4