methyl 4-((2-benzoylhydrazono)methyl)benzoate | 342002-85-1

• 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 4-((2-benzoylhydrazono)methyl)benzoate
• 英文别名: Methyl 4-[(benzoylhydrazinylidene)methyl]benzoate
• CAS: 342002-85-1
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: IQEFDHSWNZFETE-UHFFFAOYSA-N

物化性质

• 熔点：
  236 °C(Solv: ethanol (64-17-5))
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-((2-benzoylhydrazono)methyl)benzoate 在 氧气 、 copper(II) bis(trifluoromethanesulfonate) 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以88%的产率得到methyl 4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoate
  参考文献：
  名称：

  铜（II）催化亚胺C-H官能通向合成的2,5-取代的1,3,4-恶二唑‡

  摘要：

  通过使用催化量的Cu（OTf）2的N-亚芳基芳酰肼的亚胺CH功能化，可以直接获得对称和不对称的2,5-二取代的[1,3,4]-恶二唑。这是亚酰胺氧在亚胺C–H键的Cu催化氧化偶联中起亲核试剂作用的第一个例子。这些反应可以在空气中和湿气中进行，使其特别适用于有机合成。

  DOI：

  10.1021/ol202409r
• 作为产物：
  描述：

  苯甲酸 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.05h， 生成 methyl 4-((2-benzoylhydrazono)methyl)benzoate
  参考文献：
  名称：

  Rescuing the CFTR protein function: Introducing 1,3,4-oxadiazoles as translational readthrough inducing drugs

  摘要：

  Nonsense mutations in the CFTR gene prematurely terminate translation of the CFTR mRNA leading to the production of a truncated protein that lacks normal function causing a more severe form of the cystic fibrosis (CF) disease. About 10% of patients affected by CF show a nonsense mutation. A potential treatment of this alteration is to promote translational readthrough of premature termination codons (PTCs) by Translational Readthrough Inducing Drugs (TRIDs) such as PTC124. In this context we aimed to compare the activity of PTC124 with analogues differing in the heteroatoms position in the central heterocyclic core. By a validated protocol consisting of computational screening, synthesis and biological tests we identified a new small molecule (NV2445) with 1,3,4-oxadiazole core showing a high read through activity. Moreover, we evaluated the CFTR functionality after NV2445 treatment in CF model systems and in cells expressing a nonsense-CFTR-mRNA. Finally, we studied the supramolecular interactions between TRIDs and CFTR-mRNA to assess the biological target/mechanism and compared the predicted ADME properties of NV2945 and PTC124. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.09.057

文献信息

• Boron Chelates Derived from <i>N</i>-Acylhydrazones as Radical Acceptors: Photocatalyzed Coupling of Hydrazones with Carboxylic Acids
  作者：Igor A. Dmitriev、Vitalij V. Levin、Alexander D. Dilman

  DOI：10.1021/acs.orglett.1c03501

  日期：2021.11.19

  Difluoroboryl complexes obtained from N-acyl hydrazones upon brief treatment with boron trifluoride and allylic silane serve as efficient acceptors of alkyl radicals. The reaction of the boryl chelates with carboxylic acids in the presence of an acridine-type photocatalyst leading to N-acyl hydrazides is described. The efficiency of addition at the C═N bond of the chelates is determined by the formation

  用三氟化硼和烯丙基硅烷短暂处理后从N-酰基腙中获得的二氟硼基配合物可作为烷基自由基的有效受体。描述了硼基螯合物与羧酸在吖啶型光催化剂存在下产生N-酰基酰肼的反应。在螯合物的 C=N 键上的加成效率取决于由含硼杂环稳定的氮中心自由基的形成。
• Synthesis of amino-diamondoid pharmacophores <i>via</i> photocatalytic C–H aminoalkylation
  作者：William K. Weigel、Hoang T. Dang、Hai-Bin Yang、David B. C. Martin

  DOI：10.1039/d0cc02804e

  日期：——

  direct C–H aminoalkylation reaction using two light-activated H-atom transfer catalyst systems that enable the introduction of protected amines to native adamantane scaffolds with C–C bond formation. The scope of adamantane and imine reaction partners is broad and deprotection provides versatile amine and amino acid building blocks. Using readily available chiral imines, the enantioselective synthesis

  我们报告了使用两种光活化 H 原子转移催化剂系统的直接 C-H 氨基烷基化反应，该反应能够将受保护的胺引入具有 C-C 键形成的天然金刚烷支架。金刚烷和亚胺反应伙伴的范围很广，去保护提供了通用的胺和氨基酸构建块。使用容易获得的手性亚胺，还描述了沙格列汀核心和金刚乙胺衍生物的对映选择性合成。
• Photoredox Fluoroalkylation of Hydrazones in Neutral and Reductive Modes
  作者：Boris A. Worp、Mikhail D. Kosobokov、Vitalij V. Levin、Alexander D. Dilman

  DOI：10.1002/adsc.202001381

  日期：2021.2.16

  Visible light promoted fluoroalkylation of hydrazones using 4‐perfluoropyridine sulfides as fluoroalkyl radical sources is described. The process can proceed in neutral and reductive modes delivering either hydrazones or hydrazines, respectively, depending on structure of starting substrates and reaction conditions. For the reductive process, ascorbic acid is used as a terminal reductant, which recycles

  描述了使用4-全氟吡啶硫醚作为氟代烷基自由基源的可见光促进的fluoro的氟代烷基化。根据起始底物的结构和反应条件，该方法可以以中性和还原模式进行，分别递送delivering或肼。在还原过程中，抗坏血酸用作末端还原剂，可循环使用光催化剂，并作为朝向氮中心自由基的氢源。
• Cu(II) Catalyzed Imine C–H Functionalization Leading to Synthesis of 2,5-Substituted 1,3,4-Oxadiazoles
  作者：Srimanta Guin、Tuhin Ghosh、Saroj Kumar Rout、Arghya Banerjee、Bhisma K. Patel

  DOI：10.1021/ol202409r

  日期：2011.11.18

  symmetrical and unsymmetrical 2,5-disubstituted [1,3,4]-oxadiazoles has been accomplished through an imine C–H functionalization of N-arylidenearoylhydrazide using a catalytic quantity of Cu(OTf)2. This is the first example of amidic oxygen functioning as a nucleophile in a Cu-catalyzed oxidative coupling of an imine C–H bond. These reactions can be performed in air atmosphere and moisture making it exceptionally

  通过使用催化量的Cu（OTf）2的N-亚芳基芳酰肼的亚胺CH功能化，可以直接获得对称和不对称的2,5-二取代的[1,3,4]-恶二唑。这是亚酰胺氧在亚胺C–H键的Cu催化氧化偶联中起亲核试剂作用的第一个例子。这些反应可以在空气中和湿气中进行，使其特别适用于有机合成。
• Rescuing the CFTR protein function: Introducing 1,3,4-oxadiazoles as translational readthrough inducing drugs
  作者：Ivana Pibiri、Laura Lentini、Raffaella Melfi、Marco Tutone、Sara Baldassano、Paola Ricco Galluzzo、Aldo Di Leonardo、Andrea Pace

  DOI：10.1016/j.ejmech.2018.09.057

  日期：2018.11

  Nonsense mutations in the CFTR gene prematurely terminate translation of the CFTR mRNA leading to the production of a truncated protein that lacks normal function causing a more severe form of the cystic fibrosis (CF) disease. About 10% of patients affected by CF show a nonsense mutation. A potential treatment of this alteration is to promote translational readthrough of premature termination codons (PTCs) by Translational Readthrough Inducing Drugs (TRIDs) such as PTC124. In this context we aimed to compare the activity of PTC124 with analogues differing in the heteroatoms position in the central heterocyclic core. By a validated protocol consisting of computational screening, synthesis and biological tests we identified a new small molecule (NV2445) with 1,3,4-oxadiazole core showing a high read through activity. Moreover, we evaluated the CFTR functionality after NV2445 treatment in CF model systems and in cells expressing a nonsense-CFTR-mRNA. Finally, we studied the supramolecular interactions between TRIDs and CFTR-mRNA to assess the biological target/mechanism and compared the predicted ADME properties of NV2945 and PTC124. (C) 2018 Elsevier Masson SAS. All rights reserved.