N-Benzoyl-N'-p-tolyldiimid | 14572-06-6

• 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-Benzoyl-N'-p-tolyldiimid
• 英文别名: N-(4-methylphenyl)iminobenzamide
• CAS: 14572-06-6
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: IZMFQWGGMHHOIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Benzoyl-N'-p-tolyldiimid 在 乙醇 、 溶剂黄146 、 锌 作用下， 生成 1-苯甲酰基-2-(4-甲基苯基)肼
  参考文献：
  名称：

  Ponzio; Charrier, Gazzetta Chimica Italiana, 1909, vol. 39 I, p. 633

  摘要：

  DOI：
• 作为产物：
  描述：

  1-苯甲酰基-2-(4-甲基苯基)肼 在 铁酞菁 、 氧气 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 N-Benzoyl-N'-p-tolyldiimid
  参考文献：
  名称：

  酰肼和异硫氰酸酯一锅法合成 2-亚氨基-1,3,4-噻二唑啉

  摘要：

  在温和条件下成功实现了 2-亚氨基-1,3,4-噻二唑啉的一锅法合成。开发的合成包括 Fe(Pc) 催化的酰肼有氧氧化，然后是 P(NMe 2 ) 3介导的原位产生的N-酰基二氮烯与异硫氰酸酯的环化。本发明的环化显示出广泛的底物范围和良好的官能团耐受性，并且在克级上是有效的。

  DOI：

  10.1002/bkcs.12585

文献信息

• Synthesis of 2-Imino-1,3,4-thiadiazoles from Hydrazides and Isothiocyanates via Sequential Oxidation and P(NMe₂)₃-Mediated Annulation Reactions
  作者：Zhengyan Huang、Qianqian Zhang、Qiongli Zhao、Wenquan Yu、Junbiao Chang

  DOI：10.1021/acs.orglett.0c01393

  日期：2020.6.5

  N-acyldiazenes with isothiocyanates, producing 2-imino-1,3,4-thiadiazoles, is reported. This reaction proceeds well with crude N-acyldiazenes derived from the oxidation of hydrazides by iodine and permits the sequential synthesis of products directly from hydrazides without purification of the less stable N-acyldiazene intermediates. The reaction does not require transition metals and is a simple, scalable operation

  报道了AP（NMe 2）3介导的N-酰基二氮烯与异硫氰酸酯的环化反应，产生2-亚氨基-1,3,4-噻二唑。该反应与衍生自酰肼被碘氧化的粗制N-酰基二氮烯进行得很好，并允许直接从酰肼连续合成产物，而无需纯化不稳定的N-酰基二氮烯中间体。该反应不需要过渡金属，是一种简单，可扩展的操作，具有广泛的底物范围。
• Synthesis of 2‐Imino‐1,3,4‐Selenadiazoles <i>via</i> Tributylphosphine‐Mediated Annulation of <i>N</i> ‐Aroyldiazenes with Isoselenocyanates
  作者：Zhengyan Huang、Qianqian Zhang、Xiaofei Yi、Zongxiang Zhao、Wenquan Yu、Junbiao Chang

  DOI：10.1002/adsc.202100775

  日期：2021.11.9

  (PBu3)-promoted annulation reaction at room temperature. In this synthetic process, crude less stable N-aroyldiazene intermediates generated by I2-mediated oxidation of hydrazides were used directly in a subsequent annulation reaction to afford the selenadiazole products. The merits of the present synthetic strategy also include absence of transition metals and gram-scale synthesis.

  2-亚氨基-1,3,4-硒二唑衍生物可以在室温下通过连续氧化和三丁基膦 (PBu 3 ) 促进的环化反应从酰肼和异硒氰酸酯合成。在该合成过程中，由 I 2 -介导的酰肼氧化产生的较不稳定的粗N-芳酰基二氮中间体直接用于随后的环化反应，以提供硒二唑产物。本合成策略的优点还包括没有过渡金属和克级合成。
• Easy and rapid preparation of benzoylhydrazides and their diazene derivatives as inhibitors of 15-lipoxygenase
  作者：Cristian Tirapegui、Williams Acevedo-Fuentes、Pablo Dahech、Claudia Torrent、Pablo Barrias、Macarena Rojas-Poblete、Carolina Mascayano

  DOI：10.1016/j.bmcl.2017.03.017

  日期：2017.4

  Two series of diaza derivatives were prepared by solvent-free condensation of benzoic acid and 4-substituted phenylhydrazines in order to obtain phenylhydrazides (HYD series) and, by oxidation of these compounds, the corresponding benzoyldiazenes (DIA series). Both sets were evaluated as inhibitors of soybean 15-lipoxygenase activity and antioxidant capability in the FRAP and CUPRAC assays. The most potent inhibitors of both series exhibited IC50 values in the low micromolar range. Kinetic studies showed that at least the more active compounds were competitive inhibitors. Docking results indicated that the most potent inhibitor interacts strongly with Ile-839 and iron in the active site. (C) 2017 Elsevier Ltd. All rights reserved.
• DMAP-Catalyzed [2 + 4] Cycloadditions of Allenoates with <i>N</i>-Acyldiazenes: Direct Method to 1,3,4-Oxadiazine Derivatives
  作者：Qi Zhang、Ling-Guo Meng、Jinfeng Zhang、Lei Wang

  DOI：10.1021/acs.orglett.5b01237

  日期：2015.7.2

  An efficient DMAP-catalyzed [2 + 4] cycloaddition of allenoates and N-acyldiazenes is reported. The reaction involved embeddhig three heteroatoms into a six-membered ring and generated 1,3,4-oxadiazine derivatives in moderate to good yields.