(E)-N'-(thiophen-2-ylmethylene)benzohydrazide | 84889-00-9

• 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: (E)-N'-(thiophen-2-ylmethylene)benzohydrazide
• 英文别名: Benzoic acid, 2-thenylidenehydrazide；N-[(E)-thiophen-2-ylmethylideneamino]benzamide
• CAS: 84889-00-9
• 化学式: C₁₂H₁₀N₂OS
• mdl: MFCD00447980
• 分子量: 230.29
• InChiKey: CSNLKZXFSZSMCJ-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 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：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N'-(thiophen-2-ylmethylene)benzohydrazide 生成 (Z)-N'-(thiophen-2-ylmethylene)benzhydrazide
  参考文献：
  名称：

  有机化合物及其制备方法、显示基板和显示装置

  摘要：

  公开一种有机化合物及其制备方法、显示基板和显示装置，涉及显示技术领域，用于提高显示装置的显示效果与使用寿命。该有机化合物的结构式如下式(I)所示：

  公开号：

  CN114369059A
• 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 (E)-N'-(thiophen-2-ylmethylene)benzohydrazide
  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

• Stereocontrol in Synthesis of Homoallylic Amines. Syn Selective Direct Allylation of Hydrazones with Allylboronic Acids
  作者：Arindam Das、Rauful Alam、Lars Eriksson、Kálmán J. Szabó

  DOI：10.1021/ol501699x

  日期：2014.7.18

  Allylboronic acids directly react with acyl hydrazones, affording homoallylic amine derivatives. The reaction proceeds with very high syn selectivity, which is the opposite of the stereochemistry observed for allylboration of imines. The reaction can be carried out with both aromatic and aliphatic acyl hydrazones. Based on our studies the excellent syn stereochemistry can be explained by chelation

  烯丙基硼酸直接与酰基反应，得到均烯丙基胺衍生物。该反应以非常高的顺式选择性进行，这与亚胺的烯丙基硼化所观察到的立体化学相反。该反应可以与芳族和脂肪族酰基一起进行。根据我们的研究，优异的顺式立体化学可以通过酰基和B（OH）2部分的螯合控制来解释。
• Autotandem Catalyst: From Acylhydrazones to <i>N</i>′,<i>N</i>′-Methylaliphatic Acylhydrazides via Transfer Hydrogenation/<i>N</i>-Methylation with Methanol Catalyzed by a Cp* Iridium Complex Bearing a Functional Ligand
  作者：Shiyuan Luo、Xiangchao Xu、Peng Zhang、Qixun Shi、Xiaoguang Yang、Feng Li

  DOI：10.1021/acs.orglett.2c03719

  日期：2022.12.16

  A new strategy for the synthesis of N′,N′-methylaliphatic acylhydrazides from acylhydrazones via transfer hydrogenation/N-methylation with methanol as both the hydrogen source and the methylating reagent has been proposed and accomplished. In the presence of [Cp*Ir(2,2′-bpyO)(H2O)] (1 mol %) and Cs2CO3 (0.3 equiv), a range of desired products were obtained in high yields. It was also confirmed that

  提出并实现了以甲醇为氢源和甲基化试剂，通过转移氢化/ N-甲基化从酰肼合成N '，N'-甲基脂肪酰肼的新策略。在 [Cp*Ir(2,2'-bpyO)(H 2 O)]（1 mol %）和 Cs 2 CO 3（0.3 当量）的存在下，以高产率获得了一系列所需的产物。还证实了催化剂的 bpy 配体中的功能单元对铱配合物的催化活性至关重要。还介绍了本催化体系的机理研究和实际应用。
• Rao, Sayaji; Hussain Reddy, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1996, vol. 35, # 8, p. 681 - 686
  作者：Rao, Sayaji、Hussain Reddy

  DOI：——

  日期：——
• Palla, Gerardo; Pelizzi, Corrado; Predieri, Giovanni, Gazzetta Chimica Italiana, 1982, vol. 112, # 7/8, p. 339 - 342
  作者：Palla, Gerardo、Pelizzi, Corrado、Predieri, Giovanni、Vignali, Carlo

  DOI：——

  日期：——
• Indium-Mediated Asymmetric Allylation of Acylhydrazones Using a Chiral Urea Catalyst
  作者：Kian L. Tan、Eric N. Jacobsen

  DOI：10.1002/anie.200603354

  日期：2007.2.12