benzylidene acetophenone benzoyl hydrazone | 80884-00-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: benzylidene acetophenone benzoyl hydrazone
• 英文别名: N-(1,3-diphenylprop-2-enylideneamino)benzamide
• CAS: 80884-00-0
• 化学式: C₂₂H₁₈N₂O
• mdl: MFCD00540952
• 分子量: 326.398
• InChiKey: HFXMSEOARJHWKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzylidene acetophenone benzoyl hydrazone 在 碘苯 、 tetrabutylammonium tetrafluoroborate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以55 %的产率得到(3,5-diphenyl-1H-pyrazol-1-yl)(phenyl)methanone
  参考文献：
  名称：

  高价碘介导的分子内C-N偶联电催化合成取代吡唑

  摘要：

  已发现α、β-不饱和腙的电化学分子内交叉脱氢 C( sp 2 )-H/N-H 偶联，生成取代的吡唑。该过程由芳基碘在氟化醇介质中的阳极氧化原位产生的高价碘物质催化。CV 和 NMR 实验证实了高价碘化合物的形成及其在新 C-N 键构建中的关键作用。以 46% 至 88% 的产率获得了广泛的取代吡唑。

  DOI：

  10.1002/adsc.202200696
• 作为产物：
  描述：

  苯甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 benzylidene acetophenone benzoyl hydrazone
  参考文献：
  名称：

  Hydrothermal synthesis, structures, luminescence and magnetic properties of Zn(II) and Cu(II) complexes with new hydrazone ligand

  摘要：

  Two new complexes [Zn(HL)(2)(PY)(2)] (1) and [Cu(HL)](2) (2) have been synthesised from a bidentate Schiff base ligand HL (benzylidene acetophenone benzoyl hydrazone). The crystal structures of complex 1 and complex 2 were determined by single-crystal X-ray diffraction. The data indicate that: the complex 1 crystallizes in the monoclinic space group P2(1)/n, with a (nm) = 1.35816(8), b (nm) = 2.39486(13), c (nm) = 1.41368(8), alpha (degrees) = 90, beta (degrees) = 96.0840(10), gamma (degrees) = 90, Z = 4. The complex 2 crystallizes in the triclinic space group P-1, with a (nm) = 1.02483(8), b (nm) = 1.35797(11), c (nm) = 1.38271(11), alpha (degrees) = 71.5020(10), beta (degrees) = 78.5850(10), gamma (degrees) = 74.3110(10), Z = 1. Moreover, the unsaturated coordination site of metal ion is occupied by secondary ligand of pyridine. The mononuclear units in 1 and 2 are packed through weak C-H center dot center dot center dot pi and pi-pi interactions respectively. The results of analytical, IR and TG analysis studies are presented in this paper. Both the ligand and complex 1 show fluorescence in DMF solutions at room temperature. The complex 2 variable-temperature (300-1.8 K) magnetic test show that there is ferromagnetic intramolecular interaction and weak antiferromagnetic intermolecular interaction. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.11.008

文献信息

• Rh-Catalyzed Chemo- and Enantioselective Hydrogenation of Allylic Hydrazones
  作者：Qiupeng Hu、Yanhua Hu、Yang Liu、Zhenfeng Zhang、Yangang Liu、Wanbin Zhang

  DOI：10.1002/chem.201605579

  日期：2017.1.23

  A highly efficient P‐stereogenic diphosphine–rhodium complex was applied to the chemo‐ and enantioselective hydrogenation of allylic hydrazones for the synthesis of chiral allylic hydrazines in 89–96 % yields and with 82–99 % ee values. This methodology was successfully applied to the preparation of versatile chiral allylic amine derivatives.

  高效的对映异构二膦-铑配合物用于烯丙基的化学和对映选择性氢化，可合成手性烯丙基肼，产率为89-96％，ee值为82-99％  。该方法成功地用于制备通用的手性烯丙基胺衍生物。
• Hydrothermal synthesis, structures, luminescence and magnetic properties of Zn(II) and Cu(II) complexes with new hydrazone ligand
  作者：Chang-zheng Zheng、Liang Wang、Juan Liu

  DOI：10.1016/j.molstruc.2011.11.008

  日期：2012.6

  Two new complexes [Zn(HL)(2)(PY)(2)] (1) and [Cu(HL)](2) (2) have been synthesised from a bidentate Schiff base ligand HL (benzylidene acetophenone benzoyl hydrazone). The crystal structures of complex 1 and complex 2 were determined by single-crystal X-ray diffraction. The data indicate that: the complex 1 crystallizes in the monoclinic space group P2(1)/n, with a (nm) = 1.35816(8), b (nm) = 2.39486(13), c (nm) = 1.41368(8), alpha (degrees) = 90, beta (degrees) = 96.0840(10), gamma (degrees) = 90, Z = 4. The complex 2 crystallizes in the triclinic space group P-1, with a (nm) = 1.02483(8), b (nm) = 1.35797(11), c (nm) = 1.38271(11), alpha (degrees) = 71.5020(10), beta (degrees) = 78.5850(10), gamma (degrees) = 74.3110(10), Z = 1. Moreover, the unsaturated coordination site of metal ion is occupied by secondary ligand of pyridine. The mononuclear units in 1 and 2 are packed through weak C-H center dot center dot center dot pi and pi-pi interactions respectively. The results of analytical, IR and TG analysis studies are presented in this paper. Both the ligand and complex 1 show fluorescence in DMF solutions at room temperature. The complex 2 variable-temperature (300-1.8 K) magnetic test show that there is ferromagnetic intramolecular interaction and weak antiferromagnetic intermolecular interaction. (C) 2011 Elsevier B.V. All rights reserved.
• Electrocatalytic Synthesis of Substituted Pyrazoles <i>via</i> Hypervalent Iodine Mediated Intramolecular C−N Coupling
  作者：Stanislav A. Paveliev、Oleg O. Segida、Oleg V. Bityukov、Hai‐Tao Tang、Ying‐Ming Pan、Gennady I. Nikishin、Alexander O. Terent'ev

  DOI：10.1002/adsc.202200696

  日期：2022.11.22

  C(sp2)−H/N−H coupling of α,β-unsaturated hydrazones resulting in substituted pyrazoles has been discovered. The process is catalyzed by hypervalent iodine species generated in situ through anodic oxidation of aryl iodide in fluorinated alcohol media. The formation of hypervalent iodine compound and its key role in the construction of a new C−N bond was confirmed with CV and NMR experiments. A wide range

  已发现α、β-不饱和腙的电化学分子内交叉脱氢 C( sp 2 )-H/N-H 偶联，生成取代的吡唑。该过程由芳基碘在氟化醇介质中的阳极氧化原位产生的高价碘物质催化。CV 和 NMR 实验证实了高价碘化合物的形成及其在新 C-N 键构建中的关键作用。以 46% 至 88% 的产率获得了广泛的取代吡唑。