(E)-2-amino-N'-(1-phenylethylidene)benzohydrazide | 101091-14-9

• 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)-2-amino-N'-(1-phenylethylidene)benzohydrazide
• 英文别名: acetophenone anthraniloylhydrazone；anthranilic acid-(1-phenyl-ethylidenehydrazide)；Anthranilsaeure-(1-phenyl-aethylidenhydrazid)；Acetophenon-(2-amino-benzoylhydrazon)；2-amino-N-[(E)-1-phenylethylideneamino]benzamide
• CAS: 101091-14-9
• 化学式: C₁₅H₁₅N₃O
• 分子量: 253.304
• InChiKey: BNAJERNEMBCPMD-GZTJUZNOSA-N

物化性质

• 熔点：
  174 °C
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 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：
  67.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-amino-N'-(1-phenylethylidene)benzohydrazide 在 溶剂黄146 、 sodium nitrite 作用下， 生成 3-(1-phenyl-ethylidenamino)-3H-benzo[d][1,2,3]triazin-4-one
  参考文献：
  名称：

  Heller, Journal fur praktische Chemie (Leipzig 1954), 1925, vol. <2> 111, p. 48

  摘要：

  DOI：
• 作为产物：
  描述：

  靛红酸酐 在 乙醇 、 一水合肼 作用下， 生成 (E)-2-amino-N'-(1-phenylethylidene)benzohydrazide
  参考文献：
  名称：

  Thode, Journal fur praktische Chemie (Leipzig 1954), 1904, vol. <2> 69, p. 104

  摘要：

  DOI：

文献信息

• Synthesis of Tetrahydropyridine Derivatives through a Modular Assembly Reaction Using 3,4-Dihydropyran as Dual Substrate and Template
  作者：Shaohuan Sun、Cheng Cheng、Jian Yang、Amir Taheri、Dan Jiang、Biao Zhang、Yanlong Gu

  DOI：10.1021/ol5020637

  日期：2014.9.5

  A concise method to synthesize 1,2,3,4-tetrahydropyridines is described that involves the use of 2-alkoxy-3,4-dihydropyran as a modular precursor to react with aniline and a nucleophile. In this method, the heteroatom of the dihydropyran ring was replaced by nitrogen of aniline while the nucleophile attached to its adjacent position. Various druglike polyheterocycles were prepared with this method

  描述了一种合成1,2,3,4-四氢吡啶的简洁方法，该方法涉及使用2-烷氧基-3,4-二氢吡喃作为模块前体与苯胺和亲核试剂反应。在这种方法中，二氢吡喃环的杂原子被苯胺的氮取代，而亲核试剂附着在其相邻位置。通过使用含NH 2的1，5-或1，4-双亲核试剂，用这种方法制备了各种类似药物的多杂环化合物。
• Combinatorial Synthesis of 3-Arylideneaminoquinazolin-4(1<i>H</i>)-one Derivatives Catalyzed by Iodine in Ionic Liquids
  作者：Xiang-Shan Wang、Jie Sheng、Lian Lu、Ke Yang、Yu-Ling Li

  DOI：10.1021/co1000713

  日期：2011.3.14

  A combinatorial synthesis of 3-arylideneaminoquinazolin-4(1H)-one derivatives is described by a reaction of 2-aminobenzohydrazides with two equivalents of aldehydes or ketones in ionic liquids catalyzed by iodine. Controlling the reaction temperature or reducing the activity of the substrates, respectively, the intermediate products of hydrazones were obtained first, and then they were applied to react

  通过2-氨基苯甲酰肼与二当量的醛或酮在碘催化的离子液体中的反应，描述了3-芳基氨基喹唑啉-4（1H）-一衍生物的组合合成。分别控制反应温度或降低底物的活性，首先获得的中间产物，然后将它们与各种芳族醛反应而不分离，从而导致喹唑啉酮衍生物的结构多样化。
• Recyclable gold(I)-catalyzed hydrohydrazidation of terminal alkynes towards keto-N-acylhydrazones
  作者：Siqi Liu、Jianying Li、Wenli Hu、Bin Huang、Mingzhong Cai

  DOI：10.1016/j.jorganchem.2022.122411

  日期：2022.9

  heterogeneous gold(I)-catalyzed hydrohydrazidation of terminal alkynes with diverse hydrazides has been developed in chlorobenzene at 60 °C by using an MCM-41-immobilized diphenylphosphine gold(I) complex [Ph2P-MCM-41-AuNTf2] as the catalyst, providing a novel and practical method for the synthesis of a wide variety of substituted keto-N-acylhydrazones in good to excellent yields. This heterogenized gold(I) catalyst

  使用 MCM-41 固定的二苯基膦金 (I) 配合物 [Ph 2 P-MCM-41 ，在 60 °C 的氯苯中，开发了一种简便高效的非均相金 (I) 催化的末端炔烃与多种酰肼的加氢反应。-AuNTf 2 ] 作为催化剂，为合成多种取代的酮基-N-酰基腙提供了一种新颖实用的方法，产率从良好到优异。这种异质化的金 (I) 催化剂也很容易通过过滤反应混合物来回收，并且可以回收多达八次，而没有任何明显的催化效率损失。
• Gold-Catalyzed Hydrohydrazidation of Terminal Alkynes
  作者：Dmitry P. Zimin、Dmitry V. Dar’in、Valentin A. Rassadin、Vadim Yu. Kukushkin

  DOI：10.1021/acs.orglett.8b02019

  日期：2018.8.17

  Facile gold-catalyzed hydrohydrazidation of alkynes with various hydrazides (RCONHNH2)-C-2 (R = Alk or Ar; including those with an additional nudeophilic moiety) in the presence of Ph3PAuNTf2 (6 mol %) leading to a wide range of substituted keto-N-acylhydrazones (18 examples) in excellent to good yields (99-66%) is reported. This novel metal-catalyzed coupling proceeds under mild conditions (chlorobenzene, 60 degrees C), exhibits high functional group tolerance, and is insensitive to the electronic and steric effects of the substituents in the reactants.
• Conformational Complexity in Seven-Membered Cyclic Triazepinone/Open Hydrazones. 1. 1D and 2D Variable Temperature NMR Study
  作者：Kalevi Pihlaja、Mario F. Simeonov、Ferenc Fülöp

  DOI：10.1021/jo962322k

  日期：1997.7.1

  The stereo chemistry and conformational behavior of a series of 22 2-methyl-2-alkyl(phenyl, aryl)-4-N-methyl-1,2,3,4-tetrahydro-5H-1,3,4-bnezotriazepin-5-ones and their open-chain hydrazone tautomers in various solvents were studied by 1D and 2D NMR techniques in the temperature range from 193 K to 410 K. Molecular rearrangements involving interconversions of the ring and open-chain forms (the latter via amide bond and Z/E C=N double bond isomerization), pseudorotation of the ring forms, and N-inversion processes with different rates on the NMR time scale took place, leading to the observation of average and deceptively simple H-1 and C-13 NMR spectra for most of them at room temperature.