N',N'-diethylbenzohydrazide | 33233-39-5

• 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'-diethylbenzohydrazide
• 英文别名: N,N-diethylbenzhydrazide
• CAS: 33233-39-5
• 化学式: C₁₁H₁₆N₂O
• 分子量: 192.261
• InChiKey: GBVSFRTVEHXDOF-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N',N'-diethylbenzohydrazide 在 亚硝酸特丁酯 、 氧气 作用下， 以 氯仿 为溶剂， 以70%的产率得到N′-benzoyl-N-ethylnitrous 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：

  苯甲酸甲酯 在 Ru-MACHO 、 potassium tert-butylate 、 一水合肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 28.0h， 生成 N',N'-diethylbenzohydrazide
  参考文献：
  名称：

  使用醇直接催化对称，不对称的N，N-二烷基化和酰肼环化。

  摘要：

  在本文中，报道了使用醇将酰肼直接进行N，N-二烷基化。该催化方案使用各种伯醇和仲醇，具有显着的选择性和优异的收率，可以一锅法合成对称和不对称的N，N-二取代的酰肼。有趣的是，使用二醇导致酰肼的分子间环化，并且此类产物是生物活性化合物中的优先结构。水是唯一的副产物，这使得该催化方案可持续且对环境无害。

  DOI：

  10.1021/acs.orglett.0c02369

文献信息

• Synthesis of N′-propylhydrazide analogs of hydroxamic inhibitors of histone deacetylases (HDACs) and evaluation of their impact on activities of HDACs and replication of hepatitis C virus (HCV)
  作者：Maxim V. Kozlov、Konstantin A. Konduktorov、Anastasia S. Shcherbakova、Sergey N. Kochetkov

  DOI：10.1016/j.bmcl.2019.06.006

  日期：2019.8

  N′-Propylhydrazide analogs of hydroxamic inhibitors of histone deacetylases (HDACs), including tubastatin A, vorinostat and belinostat, were synthesized. All prepared compounds inhibited HDAC1/2/3, but not HDAC6, except for one hydrazide analog of HDAC4/5/7 inhibitor that was completely inactive. A novel 4-substituted derivative of N′-propylbenzohydrazide with extremely high anti-HCV activity was discovered.

  合成了组蛋白脱乙酰基酶（HDACs）的异羟肟酸抑制剂的N'-丙酰肼类似物，包括tubastatin A，vorinostat和belinostat。除了一种完全无活性的HDAC4 / 5/7抑制剂的酰肼类似物外，所有制备的化合物均抑制HDAC1 / 2/3，但不抑制HDAC6。发现了具有极高抗HCV活性的N'-丙基苯甲酰肼的新型4-取代衍生物。
• 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。
• Substituted acid derivatives useful as antidiabetic and antiobesity agents and method
  申请人：Cheng T. Peter

  公开号：US20070015797A1

  公开（公告）日：2007-01-18

  Compounds are provided which have the structure wherein Q is C or N, A is O or S, Z is O or a bond, X is CH or N and R 1 , R 2 , R 2a , R 2b , R 2c , R 3 , Y, x, m, and n are as defined herein, which compounds are useful as antidiabetic, hypolipidemic, and antiobesity agents.

  提供了一些化合物，它们的结构如下：其中Q为C或N，A为O或S，Z为O或键，X为CH或N，R1、R2、R2a、R2b、R2c、R3、Y、x、m和n如此定义，这些化合物可用作抗糖尿病、降脂和抗肥胖药物。
• Vassiliades, Bulletin de la Societe Chimique de France, 1936, vol. <5> 3, p. 160,161
  作者：Vassiliades

  DOI：——

  日期：——
• Crystal structures of two copper(II) complexes with N,N-diethylbenzhydrazide
  作者：V. Yu. Gusev、A. V. Radushev、P. A. Slepukhin、Zh. A. Vnutskikh

  DOI：10.1134/s0036023608010129

  日期：2008.1

  The copper(II) complexes with N,N-diethylbenzhydrazide, [Cu(C(6)H(5)CONHN(C(2)H(5))(2))]Cl(2) (I) and Cu(C(6)H(5)CONN(C(2)H(5))(2))(2) (II), have been studied by X-ray diffraction analysis. In the both compounds, the reactant acts as a bidentate (O, N(2)) ligand, forming five-membered chelate rings with copper. In cationic complex I, the O -> Cu and N -> Cu bond lengths are 1.954(2) and 2.070(3) A..., respectively, and the O(1)CuN(2) chelate angle is 81.89(10A degrees. The Cl(-) ions are in the coordination sphere of copper (Cu-Cl, 2.1974(11) and 2.2178(10) A...). The chelate ring has an envelope conformation with the copper atom in the flap position. The coordination polyhedron of the copper atom is a strongly distorted tetrahedron. Neutral complex II is an inner complex salt. The reactant forms with copper two planar chelate rings. The Cu-O and N -> Cu bond lengths are 1.8901(9) and 2.0175(11) A..., respectively, and the O(1)CuN(2) chelate cycle is 83.70(4)A degrees. Complex II is planar, and the coordination polygon of the copper atom is a parallelogram. The thermal stability of complexes I and II has been studied.