N',N'-二苄基苯甲酰肼 | 6304-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N',N'-二苄基苯甲酰肼
• 英文名称: N′,N′-dibenzylbenzohydrazide
• 英文别名: 2',2'-dibenzylbenzohydrazide；N',N'-dibenzylbenzohydrazide；benzoic acid-(N',N'-dibenzyl-hydrazide)；Benzoesaeure-(N',N'-dibenzyl-hydrazid)；N'-Benzoyl-N.N-dibenzyl-hydrazin；1-benzoyl-2,2-dibenzyl-hydrazine
• CAS: 6304-45-6
• 化学式: C₂₁H₂₀N₂O
• 分子量: 316.403
• InChiKey: PHJSSXNJZBVIAR-UHFFFAOYSA-N

物化性质

• 熔点：
  166 °C
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  N',N'-二苄基苯甲酰肼 在 亚硝酸特丁酯 、 氧气 作用下， 以 氯仿 为溶剂， 以75%的产率得到N′-benzoyl-N-benzylnitrous hydrazide
  参考文献：
  名称：

  C–N Bond Activation of N,N′-Dialkylacylhydrazines Mediated by β-Fragmentation of Nitrogen-Centered Radical

  摘要：

  In the presence of tert-butylnitrite and dioxygen, the C-N bond activation of N,N'-dialkylacylhydrazines was realized, providing a series of N-nitrosoacylhydrazines in high yields. Different from transition-metal and other radical catalysis, this reaction is mediated by a nitrogen-centered radical of the corresponding N,N'-dialkylacylhydrazine and further beta-fragmentation, which was supported by the mechanistic study.

  DOI：

  10.1021/acs.joc.9b01851
• 作为产物：
  描述：

  α,α-azodioxytoluene 在 盐酸 、 氯仿 作用下， 生成 N',N'-二苄基苯甲酰肼
  参考文献：
  名称：

  Behrens, Justus Liebigs Annalen der Chemie, 1902, vol. 323, p. 266,271

  摘要：

  DOI：

文献信息

• Reductive Alkylation of Hydrazine Derivatives with α-Picoline-Borane and Its Applications to the Syntheses of Useful Compounds Related to Active Pharmaceutical­ Ingredients
  作者：Tsutomu Yokomatsu、Yasushi Kawase、Takehiro Yamagishi、Jun-ya Kato、Teruo Kutsuma、Tadashi Kataoka、Takeo Iwakuma

  DOI：10.1055/s-0033-1340484

  日期：——

  ingredients of therapeutic drugs such as isocarboxazid. An efficient method for the direct reductive alkylation of hydrazine derivatives with α-picoline-borane has been developed to synthesize a variety of N-alkylhydrazine derivatives. This method provided N,N-dialkylhydrazine derivatives and N-monoalkylhydrazine derivatives upon fine-tuning of the substrates and the reagent equivalency in a one-pot manner

  摘要 已经开发了一种用α-甲基吡啶-硼烷对肼衍生物进行直接还原烷基化的有效方法，以合成多种N-烷基肼衍生物。通过一锅法对底物和试剂当量进行微调，该方法提供了N，N-二烷基肼衍生物和N-单烷基肼衍生物。该方法用于合成治疗药物如异咔唑的活性药物成分。 已经开发了一种用α-甲基吡啶-硼烷对肼衍生物进行直接还原烷基化的有效方法，以合成多种N-烷基肼衍生物。通过一锅法对底物和试剂当量进行微调，该方法提供了N，N-二烷基肼衍生物和N-单烷基肼衍生物。该方法用于合成治疗药物如异咔唑的活性药物成分。
• Phosphine-Free Ruthenium Complex-Catalyzed Synthesis of Mono- or Dialkylated Acyl Hydrazides via the Borrowing Hydrogen Strategy
  作者：Nicolas Joly、Léo Bettoni、Sylvain Gaillard、Albert Poater、Jean-Luc Renaud

  DOI：10.1021/acs.joc.1c00654

  日期：2021.5.7

  Herein, we report a diaminocyclopentadienone ruthenium tricarbonyl complex-catalyzed synthesis of mono- or dialkylated acyl hydrazide compounds using the borrowing hydrogen strategy in the presence of various substituted primary and secondary alcohols as alkylating reagents. Deuterium labeling experiments confirm that the alcohols were the hydride source in this cascade process. Density functional

  在本文中，我们报道了在各种取代的伯醇和仲醇作为烷基化试剂的情况下，使用借用氢策略，用二氨基环戊二烯酮钌三羰基络合物催化的单或二烷基化酰肼化合物的合成。氘标记实验证实，醇是该级联过程中的氢化物来源。密度泛函理论（DFT）计算揭示了单烷基化和二烷基化之间的起源和阈值。
• Synthesis and catalytic activity of half‐sandwich iridium complexes with acylhydrazone ligands for N‐alkylation of hydrazides under mild conditions
  作者：Ke Wang、Song Gao、Yu‐Zhou Luo、Zi‐Jian Yao

  DOI：10.1002/aoc.7473

  日期：——

  interaction resulted in the formation of a pseudo-octahedral geometry with the iridium center. The iridium complexes 1–4, which are stable in the presence of air and moisture, exhibit significant catalyst performance in the N-alkylation reactions of hydrazides under gentle reaction conditions. This iridium complex catalyzes various types of alcohols to undergo N-alkylation reactions with acyl hydrazides via a

  通过酰腙配体与[Cp*IrCl 2 ] 2 配位，成功合成了一种新型[Cp*IrClL]半夹心铱配合物，并利用各种光谱和分析方法进行了综合表征技术。对配合物3进行了晶体结构分析，表明酰腙配体通过涉及亚氨基氧和亚胺氮原子的双齿配位与铱配位。这种相互作用导致形成以铱为中心的伪八面体几何形状。铱配合物1-4在空气和湿气存在下稳定，在温和的反应条件下在酰肼的N-烷基化反应中表现出显着的催化性能。该铱配合物通过一锅法催化各类醇与酰肼发生N-烷基化反应，生成多种N-烷基化酰肼衍生物。该催化剂表现出卓越的催化效率、广泛的底物种类和温和的反应条件，表明其具有巨大的工业应用潜力。
• Paul, D. Brenton, Australian Journal of Chemistry, 1984, vol. 37, # 4, p. 893 - 901
  作者：Paul, D. Brenton

  DOI：——

  日期：——
• Quantitative Structure−Antifungal Activity Relationships of Some Benzohydrazides against <i>Botrytis cinerea</i>
  作者：José L. Reino、Liane Saiz-Urra、Rosario Hernández-Galán、Vicente J. Arán、Peter B. Hitchcock、James R. Hanson、Maykel Perez Gonzalez、Isidro G. Collado

  DOI：10.1021/jf0704211

  日期：2007.6.1

  Fourteen benzohydrazides have been synthesized and evaluated for their in vitro antifungal activity against the phytopathogenic fungus Botrytis cinerea. The best antifungal activity was observed for the N',N'-dibenzylbenzohydrazides 3b-d and for the N-aminoisoindoline-derived benzohydrazide 5. A quantitative structure-activity relationship (QSAR) study has been developed using a topological substructural molecular design (TOPS-MODE) approach to interpret the antifungal activity of these synthetic compounds. The model described 98.3% of the experimental variance, with a standard deviation of 4.02. The influence of an ortho substituent on the conformation of the benzohydrazides was investigated by X-ray crystallography and supported by QSAR study. Several aspects of the structure-activity relationships are discussed in terms of the contribution of different bonds to the antifungal activity, thereby making the relationships between structure and biological activity more transparent.