methyl 2-pyridyl ketone benzoylhydrazone (E-isomer)

• 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: methyl 2-pyridyl ketone benzoylhydrazone (E-isomer)
• 英文别名: (E)-N'-(1-(pyridine-2-yl)ethylidene)benzohydrazide；(E)-N'-(1-(pyridin-2-yl)ethylidene)benzohydrazide；(E)-N'-[1-(pyridin-2-yl)ethylidene]benzohydrazide；(E)-2-acetylpyridine benzoylhydrazone；2-acetylpyridine benzoylhydrazone；2-acetylpyridine phenylhydrazone；N'-[(E)-1-(2-pyridinyl)ethylidene]benzohydrazide；N-[(E)-1-pyridin-2-ylethylideneamino]benzamide
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: CNLUCMLHJNZXRT-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  三氯化锑 、 methyl 2-pyridyl ketone benzoylhydrazone (E-isomer) 以 甲醇 为溶剂， 反应 4.0h， 以69%的产率得到[2-acetylpyridinephenylhydrazonato(dichloro)antimony(III)]
  参考文献：
  名称：

  Effect of coordination to antimony(III) on the antifungal activity of 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones

  摘要：

  Antimony(III) [Sb(L)Cl-2] complexes were obtained with 2-acetylpyridine-phenylhydrazone (H2AcPh), 2-acetylpyridine-para-chloro-phenylhydrazone (H2AcpClPh), 2-acetylpyridine-para-nitro-phenylhydrazone (H2AcpNO(2)Ph) and 2-acetylpyridine-para-hydroxy-phenylhydrazone (H2AcpOHPh) along with the 2-benzoylpyridine-phenylhydrazone analogs H2BzPh, H2BzpClPh, H2BzpNO(2)Ph, H2BzpOHPh (HL). [Sb(2BzpClPh)Cl-2], complex (6), (IC50 = 4.91 +/- 1.20 mu mol L-1) was as active as nystatin (IC50= 4.44 +/- 0.76 mu mol L-1) and twofold more active than H2BzpClPh (IC50= 10.05 +/- 0.67 mu mol L-1) against Candida dubliniensis. While H2BzpClPh proved to be inactive against Candida glabrata, 6 (IC50 = 10.11 +/- 0.64 mu mol L-1) was more active than miconazole nitrate (IC50= 19.50 +/- 4.53 mu mol L-1). Similarly, H2BzpNO(2)Ph revealed to be inactive against Candida lusitaniae whereas complex [Sb(2BzpNO(2)Ph)Cl-2] (7) (IC50 = 8.54 +/- 2.21 mu mol L-1) proved to be as active as nystatin (IC50 = 5.31 +/- 0.84 mu mol L-1). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.05.004
• 作为产物：
  描述：

  2-乙酰基吡啶 、 苯甲酰肼 反应 6.0h， 以65%的产率得到methyl 2-pyridyl ketone benzoylhydrazone (E-isomer)
  参考文献：
  名称：

  仿生的氧代，二氧代和氧代过氧肼基钒（IV / V）配合物

  摘要：

  [VO（acac）2 ]与HL反应（HL是hydrHacpy-inh I或Hacpy-bhz II；acpy =乙酰吡啶，inh = 异烟酸酰肼，bhz =苯甲酰肼）在干燥状态下 甲醇得到氧杂钒（IV）配合物[VOL（acac）]（HL ＝ I：1，HL ＝ II：3）。二氧钒钒（V）络合物[VO 2 L]（HL = I：2，HL = II：4）是通过在1和3中进行空气氧化得到的。甲醇。用H 2 O 2处理1和3或2和4 产生oxoperoxovanadium（V）络合物[VO（O 2）L]（HL = I：5，HL = II：6）。在......的存在下儿茶酚 或者 苯氧肟酸，1和3得到的混合螯合物[VOL（猫）]（HL = 我：7，HL = II：8）或[VOL（BHA）]（HL = 我：9，HL = II：10）。过氧配合物5和6与DMF中的PPh 3进行氧转移反应。在DMF和二甲基亚砜，7，8，9

  DOI：

  10.1039/b202852m

文献信息

• Stereoselective, solvent free, highly efficient synthesis of aldo- and keto-N-acylhydrazones applying grindstone chemistry
  作者：José Maurício dos Santos Filho、Savio Moita Pinheiro

  DOI：10.1039/c7gc00730b

  日期：——

  A mild and efficient synthesis of N-acylhydrazones has been developed, applying a simple grindstone procedure, leading to a library of 51 examples exhibiting a broad variety of structural features, 21 of them described for the first time in this paper. This methodology works without any organic solvent under the catalysis of acetic acid at room temperature, promotes the formation of essentially pure

  已经开发出了温和而有效的N-酰基hydr酮合成方法，该方法采用了简单的磨石程序，从而产生了51个实例，这些实例均显示出多种结构特征，其中21个实例首次在本文中进行了描述。该方法在室温下在乙酸催化下无需任何有机溶剂即可工作，可促进形成基本纯净的粗产物，并避免繁琐的后处理和有害溶剂的使用以及能耗。另外，如NMR分析所支持的，其导致N-酰基hydr的立体选择性形成。
• Mild, Stereoselective, and Highly Efficient Synthesis of<i>N</i>-Acylhydrazones Mediated by CeCl₃·7H₂O in a Broad Range of Solvents
  作者：José Maurício dos Santos Filho

  DOI：10.1002/ejoc.201402609

  日期：2014.10

  This method uses a minimal catalytic amount of cerium(III), is stereoselective, and offers several unique features, such as compatibility with aryl, heterocyclic, alkenyl, and sensitive functional groups as well as the ability to prepare N-acylhydrazones from highly hindered substrates. More strikingly, cerium(III) efficiently mediated the reaction with less reactive substrates such as diaryl and alkyl

  在一种温和而实用的方法中，酰肼和醛在氯化铈 (III) 介导下发生缩合反应，迅速转化为 N-酰基腙。该方法使用最低催化量的铈 (III)，具有立体选择性，并提供了几个独特的功能，例如与芳基、杂环、烯基和敏感官能团的相容性以及从高度受阻的底物制备 N-酰基腙的能力. 更引人注目的是，当没有催化剂的经典方案无效时，铈 (III) 可以有效地介导与反应性较低的底物（如二芳基和烷基芳基酮）的反应。该方法能够合成结构多样的 N-酰基腙库，这些库在合成和药物化学中具有应用。
• Potentially Tridentate Hydrazonic Ligands in the Synthesis of Methyl and Acetyl Palladium(II) Complexes
  作者：Paolo Pelagatti、Mauro Carcelli、Francesca Franchi、Corrado Pelizzi、Alessia Bacchi、Andrea Fochi、Hans-Werner Frühauf、Kees Goubitz、Kees Vrieze

  DOI：10.1002/(sici)1099-0682(200003)2000:3<463::aid-ejic463>3.0.co;2-6

  日期：2000.3

  tridentate hydrazonic ligands of the type HNNO have been used in the synthesis of some methyl palladium(II) complexes. Depending on the applied experimental conditions two different kinds of complexes are obtained. Thus, the reactions between HL1–HL5 and (COD)PdMeCl in diethyl ether led to the formation of bidentate methyl complexes of the type Pd(HNN)MeCl (1–5), where the ligands maintain a neutral character

  HNNO 类型的潜在三齿腙配体已用于合成一些甲基钯 (II) 配合物。根据所应用的实验条件，可以获得两种不同的配合物。因此，HL1-HL5 和 (COD)PdMeCl 在乙醚中的反应导致形成 Pd(HNN)MeCl (1-5) 类型的二齿甲基配合物，其中配体保持中性特征。然而，在碱如 Et3N 或 NaOMe 的存在下，配体去质子化，随后形成 Pd(NNO)Me (7-10) 类型的三齿甲基配合物。在溶液中，配合物 1-5 往往会随着甲烷的消除和三齿氯化物配合物 Pd(NNO)Cl 的形成而失去腙质子 (6)；这种趋势可能与已确定的游离配体的酸度相关。将一氧化碳通过 1-5 的溶液鼓泡，形成相应的乙酰配合物 Pd(HNN)[C(O)Me]Cl (11-15)，其中存在顺式和反式异构体。它们的摩尔比是根据基于电子考虑的分子模型研究的结果合理化的。在三齿配合物 7-10 的羰基化中发现了一种显
• Fast Synthesis of <i>N</i>-Acylhydrazones Employing a Microwave Assisted Neat Protocol
  作者：Marta M. Andrade、Maria Teresa Barros

  DOI：10.1021/cc9001444

  日期：2010.3.8

  A variety of N-acylhydrazones were synthesized Under microwave irradiation within 2.5-10 min, starting from benzo, salicyloyl, and isonicotinic hydrazides. The protocol developed employs microwave irradiation in the absence of solvents and catalysts, leading to high yields. The results are reproducible in a 500 mg to 5 g scale.
• Synthesis, characterization, crystal structure, and DNA binding of two copper(II)–hydrazone complexes
  作者：Madshusudan Nandy、David L. Hughes、Georgina M. Rosair、Raj Kumar Bhubon Singh、Samiran Mitra

  DOI：10.1080/00958972.2014.964697

  日期：2014.10.18

  Two new Cu(II)-hydrazone complexes, [Cu(L)(Hbpe)ClO4]center dot ClO4 center dot[Cu(L)Cl] (1) and [Cu (HL)(2)]center dot 1.5ClO(4)center dot 0.5OH (2) (where HL = (E)-N'-(1-(pyridine-2-yl)ethylidene)benzohydrazide and bpe = trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene), have been synthesized and characterized by physicochemical methods. The structures of the complexes have been established by single-crystal X-ray diffraction direct methods, which reveal that the metal ions have distorted square-pyramidal and square-planar geometries in 1, and a distorted octahedral geometry in 2. DNA binding of HL, 1, and 2, performed by UV-vis titration in tris-buffer medium, yielded binding constants, which are 9.5 x 10(3), 1.88 x 10(4), and 4.66 x 10(4) M-1, respectively. Viscosity measurements suggest a surface or groove-binding mode of interaction between CT-DNA with HL, 1, and 2.