对硝基苯甲醛苯甲酰腙 | 59394-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 对硝基苯甲醛苯甲酰腙
• 英文名称: (E)-N'-(4-nitrobenzylidene)benzohydrazide
• 英文别名: N'-(4-Nitrobenzylidene)benzohydrazide；N-[(E)-(4-nitrophenyl)methylideneamino]benzamide
• CAS: 59394-91-1
• 化学式: C₁₄H₁₁N₃O₃
• 分子量: 269.26
• InChiKey: MVQGNPRBTFWEMO-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 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：
  87.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对硝基苯甲醛苯甲酰腙 在 potassium permanganate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.25h， 以96%的产率得到2-(4-硝基苯基)-5-苯基-1,3,4-恶二唑
  参考文献：
  名称：

  微波辅助合成2,5-二取代1,3,4-恶二唑

  摘要：

  通过在固体矿物载体的表面上以及在丙酮和水的混合物中于微波辐射下用高锰酸钾氧化1-芳基-2-亚芳基肼来合成2,5-二取代的1,3,4-恶二唑。

  DOI：

  10.1016/j.tetlet.2004.09.095
• 作为产物：
  描述：

  苯甲酸 在 硫酸 、 一水合肼 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成 对硝基苯甲醛苯甲酰腙
  参考文献：
  名称：

  Modulation of estrogen-related receptors subtype selectivity: Conversion of an ERRβ/γ selective agonist to ERRα/β/γ pan agonists

  摘要：

  Estrogen Related Receptors (ERRs) are key regulators of energy homeostasis and play important role in the etiology of metabolic disorders, skeletal muscle related disorders, and neurodegenerative diseases. Among the three ERR isoforms, ERR alpha emerged as a potential drug target for metabolic and neurodegenerative diseases. Although ERR beta/gamma selective agonist chemical tools have been identified, there are no chemical tools that effectively target ERR alpha agonism. We successfully engineered high affinity ERR alpha agonism into a chemical scaffold that displays selective ERR beta/gamma agonist activity (GSK4716), providing novel ERR alpha/beta/gamma pan agonists that can be used as tools to probe the physiological roles of these nuclear receptors. We identified the structural requirements to enhance selectivity toward ERR alpha. Molecular modeling shows that our novel modulators have favorable binding modes in the LBP of ERR alpha and can induce conformational changes where Phe328 that originally occupies the pocket is dislocated to accommodate the ligands in a rather small cavity. The best agonists up-regulated the expression of target genes PGC-1 alpha and PGC-1 beta, which are necessary to achieve maximal mitochondrial biogenesis. Moreover, they increased the mRNA levels of PDK4, which play an important role in energy homeostasis.

  DOI：

  10.1016/j.bioorg.2020.104079

文献信息

• Synthesis, oxidation and dehydrogenation of cyclic N,O- and N,S-acetals. Part III. Transformation of N,O-acetals: 3-acyl-1,3,4-oxadiazolines
  作者：László Somogyi

  DOI：10.1002/jhet.5570440603

  日期：2007.11

  Various aldehyde and ketone acylhydrazones are synthesized and, under acylating conditions, cyclized into 3-acyl-1,3,4-oxadiazolines. The scope and limitations of these cyclizations and the possible side reactions (e.g. formation of the open-chain N,O-acylhydrazinocarbinols) are dissected. For the first time, simple, convenient and efficient dehydrogenations of 3-acyl-1,3,4-oxadiazolines to oxadiazoles

  合成了各种醛和酮酰基hydr，并在酰化条件下将其环化成3-酰基-1,3,4-恶二唑啉。剖析了这些环化作用的范围和局限性以及可能的副反应（例如，形成开链的N，O-酰基肼基碳氢化合物）。首次提出了通过高锰酸钾或更简单地用硝酸铈铈（IV）铵（CAN）处理将3-酰基-1,3,4-恶二唑啉简单，方便，有效地脱氢为恶二唑的方法。2,2-二取代的3-酰基-1,3,4-恶二唑啉以及醛二酰基hydr的CAN氧化（2,5-二取代的3-酰基-1,3,4-恶二唑啉的开链异构体）再生母体羰基化合物。
• Sustainable Synthesis of Oximes, Hydrazones, and Thiosemicarbazones under Mild Organocatalyzed Reaction Conditions
  作者：Sara Morales、José Luis Aceña、José Luis García Ruano、M. Belén Cid

  DOI：10.1021/acs.joc.6b01912

  日期：2016.10.21

  thiosemicarbazones derived from aromatic and aliphatic aldehydes using equimolar amounts of reagents and green solvents. Experimental simplicity and excellent yields after a simple filtration are the main advantages of the method, being an alternative to those currently available especially for the acyl derivatives, which do not work under uncatalyzed conditions. Its application to the synthesis of acyloximes by

  吡咯烷很有效地催化，大概是通过亚胺基活化，使用等摩尔量的试剂和绿色溶剂，形成了芳香族和脂肪族醛衍生的酰基肟，酰基hydr和硫代半氨基甲酮。该方法的主要优点是实验简单，过滤简单后的优异收率，是目前可用于那些特别是酰基衍生物的替代方法，这些方法在未催化条件下不起作用。通过醛和酰基羟胺之间的直接缩合将其用于合成酰基肟的应用是空前的。
• Lanthanide–EDTA complexes covalently bonded on Fe₃O₄@SiO₂ magnetic nanoparticles promote the green, stereoselective synthesis of <i>N</i>-acylhydrazones
  作者：João Batista M. de Resende Filho、Nathália Kellyne S. M. Falcão、Gilvan P. Pires、Luiz Fernando S. de Vasconcelos、Sávio M. Pinheiro、José Maurício dos Santos Filho、Marília Imaculada Frazão Barbosa、Antônio Carlos Doriguetto、Ercules E. S. Teotonio、Juliana A. Vale

  DOI：10.1039/c9nj02916h

  日期：——

  and applicability of green procedures. In this work, lanthanide–EDTA complexes covalently bonded on Fe3O4@SiO2 magnetic nanoparticles (Fe3O4@SiO2-xN-EDTA–Ln3+, with x = 1, 2, or 3 N spacer groups, and Ln3+ = La3+, Ce3+, Sm3+, Eu3+, Gd3+, Tb3+, Er3+ or Yb3+) were prepared and investigated as a heterogeneous catalyst for the synthesis of N-acylhydrazones. The target molecules were obtained in good to excellent

  在最近几年中，已经开发出许多使用磁性纳米材料基催化剂的合成方法，这些方法对于绿色工艺的效率，选择性和适用性具有相当大的优势。在这项工作中，镧系元素-EDTA络合物共价键合在Fe 3 O 4 @SiO 2磁性纳米颗粒上（Fe 3 O 4 @SiO 2 - x N-EDTA-Ln 3+，其中x = 1、2或3 N间隔基并且Ln 3+ = La 3+，Ce 3+，Sm 3+，Eu 3+，Gd 3+，Tb 3+，Er制备了3+或Yb 3+）并作为合成N-酰基hydr的非均相催化剂进行了研究。在温和条件下反应时间短，易回收催化剂的浓度低后，仅以E-非对映异构体的形式获得了高至优异收率的目标分子。
• Allyltrimethoxysilane Addition to<i>N</i>-Acylhydrazones: Two Catalytic Methods Employing CuCl and Fluoride
  作者：Gregory K. Friestad、Hui Ding

  DOI：10.1055/s-2004-829190

  日期：——

  Two alternative reaction conditions developed for allyl­trimethoxysilane addition to N-benzoylhydrazones enable efficient and versatile access to homoallylic α-branched amines. Aldehyde hydrazones, both aromatic and aliphatic, and ketone hydrazones all give good yields. One set of conditions employs catalytic amounts of CuCl and tetrabutylammonium triphenyldifluorosilicate (TBAT); improved yields and reaction times are obtained at 80 °C in the presence of bis(diphenylphosphino)ethane (dppe) and t-BuOH as additives. The second set of conditions employs 20 mol% TBAT as a fluoride source in a metal-free catalytic system; here t-BuOH offers only modest improvement, and ambient temperatures are optimal. For example, under this second set of conditions, the N-benzoylhydrazone from ethyl pyruvate affords the homoallylic tert-alkyl amine adduct in 78% yield.

  针对烯丙基三甲氧基硅烷与 N-苯甲酰肼的加成反应开发出了两种替代反应条件，从而能够高效、多用途地获得均烯丙基δ-±-支链胺。芳香族和脂肪族的醛肼以及酮肼都有很好的产率。其中一套条件使用了催化量的 CuCl 和四丁基三苯基二氟硅酸铵 (TBAT)；在 80 °C 温度下，以双（二苯基膦）乙烷 (dppe) 和 t-BuOH 作为添加剂，可提高产率并缩短反应时间。第二套条件是在无金属催化体系中使用 20 mol% 的 TBAT 作为氟源；t-BuOH 在此条件下只能起到适度的改善作用，而环境温度则是最佳条件。例如，在第二套条件下，丙酮酸乙酯中的 N-苯甲酰基腙可生成均烯丙基叔烷基胺加合物，收率为 78%。
• Crystal structure of benzoic acid 4-nitrobenzylidenhydrazide
  作者：Yu. M. Chumakov、Z. A. Starikova、B. Ya. Antosyak、V. I. Tzapkov、N. M. Samus、A. P. Gulya

  DOI：10.1007/s10947-006-0056-7

  日期：2005.3

  The crystal structure of benzoic acid 4-nitrobenzylidenhydrazide has been determined. Crystal data: crystal system — monoclinic, a = 7.101(9) Å, b = 25.48(3) Å, c = 7.730(11) Å; β = 112.43(9)°, space group P21/n, Z = 4, R = 0.038. The compound under investigation has a non-planar structure in general, and the substituents at azomethine N-C bond are in E-position. Root-mean-square planes of the six-memebered heterocycles make angles of 29.9° and 37.7° to fairly planar hydrazine fragment. In crystalline state the compound forms layers, the molecules within the layers being linked by C-H...O bonds. Neighboring layers are connected by hydrogen bonds between carbonyl oxygen atoms and amide hydrogens.

  确定了苯甲酸 4-硝基亚苄基肼的晶体结构。晶体数据：晶系-单斜，a = 7.101(9) Å，b = 25.48(3) Å，c = 7.730(11) Å；β = 112.43(9)° ，空间群 P21/n，Z = 4，R = 0.038。所研究的化合物总体上具有非平面结构，偶氮甲基 N-C 键上的取代基处于 E 位。六分子杂环的均方根平面与相当平面的肼片段分别成 29.9° 和 37.7° 角。在结晶状态下，化合物形成层，层内分子通过 C-H...O 键连接。相邻层通过羰基氧原子和酰胺氢原子之间的氢键连接。