N'-(2-hydroxynaphthylidene)-4-chlorobenzohydrazide | 73703-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N'-(2-hydroxynaphthylidene)-4-chlorobenzohydrazide
• 英文别名: INP0400；p-Chlorbenzoesaeure-naphthalhydrazid；4-chloro-N-[(2-hydroxynaphthalen-1-yl)methylideneamino]benzamide
• CAS: 73703-08-9
• 化学式: C₁₈H₁₃ClN₂O₂
• mdl: MFCD01057515
• 分子量: 324.766
• InChiKey: IPAUMSQKBXLIJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N'-(2-hydroxynaphthylidene)-4-chlorobenzohydrazide 在 三氟化硼乙醚 、 lead(IV) tetraacetate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (1-(4-chlorobenzoyl)naphthalen-2-yl)(2,4,6-trimethoxyphenyl)methanone
  参考文献：
  名称：

  BF3-催化的2-甲酰基芳基酮与富电子芳烃/杂芳烃的串联反应：异苯并呋喃的集合体。

  摘要：

  已经描述了一种高效率且高产率的，由BF 3 ·Et 2 O催化的化学选择性合成多种1,3-二芳基异苯并呋喃的方法。该反应通过2-甲酰基芳基酮与富电子芳烃/杂芳烃之间的依次加氢芳基化-环化进行。所开发方法的优点包括操作简便，广泛的底物范围以及对克级合成的适用性。异苯并呋喃衍生物作为二烯的用途扩展到了用DMAD合成[4 + 2]环加合物和高产率合成1,2-二羰基芳烃。

  DOI：

  10.1039/d0cc02760j
• 作为产物：
  描述：

  4-氯苯甲酰肼 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到N'-(2-hydroxynaphthylidene)-4-chlorobenzohydrazide
  参考文献：
  名称：

  一种高效的三官能团联苯的Pd（II）配合物，用于芳基溴化物的Heck反应

  摘要：

  报告了空气和热稳定的三官能O，N和O-叔齿苯并PPd（II）配合物的合成，并通过元素分析，光谱方法和单晶X射线晶体学技术对其进行了表征。这种新型可重复使用的均相催化剂已在温和的反应条件下有效地用于活化和失活的芳基溴化物与各种烯烃的Mizoroki-Heck反应，产率高达99％，优良率极高。

  DOI：

  10.1016/j.tetlet.2015.05.016

文献信息

• Synthesis and molecular structure of ruthenium(III) benzoylhydrazone complexes: Substituents effect on transfer hydrogenation of ketones
  作者：Appukutti Kanchanadevi、Rengan Ramesh、Nattamai Bhuvanesh

  DOI：10.1016/j.jorganchem.2015.04.032

  日期：2015.7

  in these complexes. Further, the complexes 1–5 have been proven to catalyse the transfer hydrogenation of linear, cyclic and aromatic ketones to their corresponding secondary alcohols in the presence of i-PrOH/KOH at 82 °C and the maximum conversion is up to 99%. The effect of other variables on the transfer hydrogenation reaction such as solvent, base, temperature, time and catalyst loading is also

  已经报道了容易且方便地合成具有通式[Ru（L）Cl（PPh 3）2 ]的苯甲酰hydr（其中L ＝ 2-羟基-1-萘醛苯甲酰hydr）的一系列新的八面体钌（III）配合物。所有配合物的组成均已通过微分析，红外，电子，磁性和EPR光谱技术明确表征。取代的苯甲酰hydr配体表现为双阴离子三齿O，N和O供体，并通过酚氧，偶氮甲碱氮和去质子化的酰胺氧。该络合物在可见光区域显示出适度强的配体-金属电荷转移跃迁，在UV区域显示出配体内跃迁。配合物的磁矩（298 K）在1.72–1.97μB的范围内，表明在金属中心存在一个不成对的电子。低自旋单核Ru（III）苯甲酰hydr配合物在冷冻溶液中显示菱形EPR光谱图。两种配合物的分子结构已通过单晶X射线晶体学确定，表明这些配合物中存在八面体几何形状失真。此外，复合物1 - 5业已证明，在i -PrOH / KOH存在下，在82°C的条件下，催化线性，环状和芳
• Synthesis, structural characterization, electrochemistry and catalytic transfer hydrogenation of ruthenium(II) carbonyl complexes containing tridentate benzoylhydrazone ligands
  作者：Rupesh Narayana Prabhu、Rengan Ramesh

  DOI：10.1016/j.jorganchem.2012.08.002

  日期：2012.11

  metal-to-ligand charge transfer (MLCT) transitions in the visible region and display one quasi-reversible reduction and two irreversible oxidations. Further, the catalytic efficiency of the complexes has been investigated in the case of transfer hydrogenation of ketones to the corresponding secondary alcohols. The influence of base, reaction temperature and catalyst loading in transfer hydrogenation reaction was

  方便合成八种具有通式[Ru（L）（CO）（EPh 3）2 ]（其中E = P或As； H 2 L =苯甲酰hydr配体，两个H's ）的八面体钌（II）羰基苯甲酰hydr络合物描述了两个可解离的质子）。取代的苯甲酰hydr配体表现为双阴离子三齿O，N和O供体（L），并通过酚盐氧，偶氮甲碱氮和去质子化的酰胺氧与钌配位。配合物的组成已通过元素分析和光谱方法（FT-IR，1 H NMR，13 C NMR，UV-vis）确定。配合物之一[Ru（L2）（CO）（PPh 3）的晶体结构2 ]（2）已通过单晶X射线晶体学解决，表明这些配合物中存在八面体几何形状的扭曲。所有的配合物在可见光区域都表现出金属到配体的电荷转移（MLCT）跃迁，并显示出一种准可逆的还原反应和两种不可逆的氧化反应。此外，在将酮转移氢化为相应的仲醇的情况下，已经研究了配合物的催化效率。还评估了碱，反应温度和催化剂在转移加氢反应中的影
• Palladium complexes catalyzed regioselective arylation of 2-oxindole via in situ C(sp2)−OH activation mediated by PyBroP
  作者：A. Vignesh、Werner Kaminsky、N. Dharmaraj

  DOI：10.1016/j.jorganchem.2016.09.026

  日期：2016.12

  Pd(II) complexes appended with ONO pincer type ligand were synthesized, structurally characterized and successfully applied as catalysts for regieoselective C−2 arylation of 2-oxindole via in situ C (sp2)−OH activation in aqueous-organic media under an open atmosphere at room-temperature. This catalyst was reused up to four cycles. Favourably, the present protocol doesn't require the addition of any

  合成，结构表征并附加了ONO钳型配体的Pd（II）配合物，已成功地用作在开放环境下通过水-有机介质中原位C（sp 2）-OH活化的2-氧吲哚的选择性C-2芳基化的催化剂室温下的气氛。该催化剂可重复使用多达四个循环。有利地，本方案不需要添加任何外部氧化剂，添加剂或相转移剂。
• An efficient trifunctional benzhydrazone ligated Pd(II) complex for Heck reaction of aryl bromides
  作者：Subramanian Muthumari、Nanjan Mohan、Rengan Ramesh

  DOI：10.1016/j.tetlet.2015.05.016

  日期：2015.7

  methods, and single crystal X-ray crystallographic technique. The new and reusable homogeneous catalyst has been effectively applied to the Mizoroki–Heck reaction of activated and deactivated aryl bromides with various olefins under mild reaction conditions in good to excellent yields up to 99%.

  报告了空气和热稳定的三官能O，N和O-叔齿苯并PPd（II）配合物的合成，并通过元素分析，光谱方法和单晶X射线晶体学技术对其进行了表征。这种新型可重复使用的均相催化剂已在温和的反应条件下有效地用于活化和失活的芳基溴化物与各种烯烃的Mizoroki-Heck反应，产率高达99％，优良率极高。
• Diarylacylhydrazones: Clostridium-selective antibacterials with activity against stationary-phase cells
  作者：Chao Chen、Naveen K. Dolla、Gabriele Casadei、John B. Bremner、Kim Lewis、Michael J. Kelso

  DOI：10.1016/j.bmcl.2013.12.015

  日期：2014.1

  Current antibiotics for treating Clostridium difficile infections (CDI), that is, metronidazole, vancomycin and more recently fidaxomicin, are mostly effective but treatment failure and disease relapse remain as significant clinical problems. The shortcomings of these agents are attributed to their low selectivity for C. difficile over normal gut microflora and their ineffectiveness against C. difficile spores. This Letter reports that certain diarylacylhydrazones identified during a high-throughput screening/counter-screening campaign show selective activity against two Clostridium species (C. difficile and Clostridium perfringens) over common gut commensals. Representative examples are shown to possess activity similar to vancomycin against clinical C. difficile strains and to kill stationary-phase C. difficile cells, which are responsible for spore production. Structure-activity relationships with additional synthesised analogues suggested a protonophoric mechanism may play a role in the observed activity/selectivity and this was supported by the well-known protonophore carbonyl cyanide m-chlorophenyl hydrazone (CCCP) showing selective anti-Clostridium effects and activity similar to diarylacylhydrazones against stationary-phase C. difficile cells. Two diarylacylhydrazones were shown to be non-toxic towards human FaDu and Hep G2 cells indicating that further studies with the class are warranted towards new drugs for CDI. (C) 2013 Elsevier Ltd. All rights reserved.