N,N′-(1,4-phenylenebis(methylene))dibenzamide | 33891-01-9

• 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: N,N′-(1,4-phenylenebis(methylene))dibenzamide
• 英文别名: N,N'-p-xylylene-bis-benzamide；N,N'-p-Xylylen-bis-benzamid；1,4-Bis-(benzoylamino-methyl)-benzol；N.N'-Dibenzoyl-p-xylylendiamin；1,4-Bis-benzoylaminomethyl-benzol；Benzene, 1,4-bis(benzoylaminomethyl)-；N-[[4-(benzamidomethyl)phenyl]methyl]benzamide
• CAS: 33891-01-9
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: PYQANETVRUWJJA-UHFFFAOYSA-N

物化性质

• 熔点：
  194 °C(Solv: ethanol (64-17-5))
• 沸点：
  667.3±48.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对苯二腈 在 tropylium tetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 N,N′-(1,4-phenylenebis(methylene))dibenzamide
  参考文献：
  名称：

  Tropyium 四氟硼酸盐促进腈、亚胺和酰胺的硼氢化

  摘要：

  腈类（现成的合成前体）转化为胺、亚胺或酰胺是合成实验室和工业化学中重要的化学转化。有各种各样的方法来促进这种类型的化学。但是，仍然存在一些限制。为了追求实用且环境友好的腈硼氢化反应，我们开发了一种新的有机催化方法，用频哪醇硼烷将腈、亚胺或酰胺还原为胺。通过将进一步的官能化反应引入到一锅中的粗硼氢化混合物中，可以方便地获得来自这些胺的有价值的衍生物。

  DOI：

  10.1039/d2gc01905a

文献信息

• Nickel-Catalyzed Phosphine Free Direct N-Alkylation of Amides with Alcohols
  作者：Jagadish Das、Debasis Banerjee

  DOI：10.1021/acs.joc.7b03215

  日期：2018.3.16

  Herein, we developed an operational simple, practical, and selective Ni-catalyzed synthesis of secondary amides. Application of renewable alcohols, earth-abundant and nonprecious nickel catalyst facilitates the transformations, releasing water as byproduct. The catalytic system is tolerant to a variety of functional groups including nitrile, allylic ether, and alkene and could be extended to the synthesis

  本文中，我们开发了一种操作简单，实用，选择性的Ni催化仲酰胺合成方法。使用可再生醇，富含地球的和非贵重的镍催化剂可促进转化，并释放水作为副产物。该催化系统对包括腈，烯丙基醚和烯烃在内的各种官能团具有耐受性，并且可以扩展到双酰胺，止吐药Tigan和多巴胺D2受体拮抗剂依托必利的合成。初步的机理研究表明，苄基CH键参与了速率测定步骤。
• 双苄酰胺类CXCR4拮抗剂及其制备和应用
  申请人：杭州师范大学

  公开号：CN113845439A

  公开（公告）日：2021-12-28

  本发明公开了双苄酰胺类CXCR4拮抗剂及其制备方法和在制备抗炎、抗肿瘤、通过拮抗CXCR4靶点来防治相关疾病的药物中的应用。双苄酰胺类CXCR4拮抗剂为具有如下通式(I)或(II)的化合物和/或及其可药用盐：本发明采用简便高效的一步法合成了一系列新型的双苄酰胺类CXCR4拮抗剂，具有抗肿瘤、抗炎、抗感染、抗自身免疫等多种药理活性，在众多疾病中具有广泛的应用优势。
• [NN]‐Chelate nickel complexes with Schiff base ligands: Synthesis, structure and catalytic activity in green amidation reaction
  作者：Wen Guo、Zhen‐Jiang Liu、Fanhong Wu、Yu‐Zhou Luo、Zi‐Jian Yao

  DOI：10.1002/aoc.6808

  日期：2022.9

  A series of N,N-coordinate nickel (II) complexes with Schiff base ligands have been synthesized. All N,N-coordinate nickel (II) complexes 1–4 were well characterized by IR and elemental analysis. Molecular structure of complex 1 was further characterized by single crystal X-ray diffraction analysis. All air and moisture stable nickel complexes showed efficient catalytic activity for the amidation reaction

  已经合成了一系列具有席夫碱配体的N , N配位镍 (II) 配合物。所有N , N配位镍 (II) 配合物1 – 4都通过 IR 和元素分析进行​​了很好的表征。配合物1的分子结构通过单晶X射线衍射分析进一步表征。所有对空气和水分稳定的镍配合物对多种酰胺和伯醇的酰胺化反应均显示出有效的催化活性。N-烷基化酰胺以良好至优异的收率得到，释放水作为唯一的副产物。多种类型的官能团在这种反应条件下耐受良好。此外，还进行了对照实验以了解这种镍催化方案。
• Lustig, Chemische Berichte, 1895, vol. 28, p. 2987
  作者：Lustig

  DOI：——

  日期：——
• Electrochemically Induced Dynamics of a Benzylic Amide [2]Catenane
  作者：Paola Ceroni、David A. Leigh、Loïc Mottier、Francesco Paolucci、Sergio Roffia、David Tetard、Francesco Zerbetto

  DOI：10.1021/jp991870+

  日期：1999.11.1

  The electrochemistry of a benzylic amide [2]catenane was investigated and compared to that of its topologically trivial components. The redox behavior of both the catenane and the uninterlocked macrocycle can be largely understood in terms of the electrochemistry of smaller molecular fragments and simple molecular orbital considerations that show that the electroactivity of the C=O groups is split into two sets of quasi-degenerate potentials separated by a substantial gap. A fast intermolecular reaction follows the reduction of the macrocycle and smaller fragments, consistent with the corresponding dimers containing a new C-C bond linking two reduced carbonyls. The cyclic voltammetric behavior of the catenane differs significantly from that of the macrocycle-a feature that must therefore be directly attributable to the mechanically interlocked molecular architecture of the catenane. In particular, an intramolecular reaction (irreversible in the CV time scale) occurs in the catenane, which is shown to be a function of temperature and scan rate. Simulation of the cyclic voltammograms shows that the intramolecular reaction occurs on a time scale wider than that of circumrotation of the two rings in the neutral molecule, thus excluding that cyclic voltammetry (CV) is monitoring the latter process, Both the analysis of the electrochemical data and semiempirical quantum chemical (MNDO) calculations would suggest that the electrochemically induced reaction in the catenane is the soldering of the two interlocked macrocycles: the formation of a C-C bond between two reduced carbonyl groups would thus prevent further rotation of the two interlocked rings.