tert-butyl-2-(4-cyanobenzylidene)hydrazinecarboxylate | 149267-91-4

• 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: tert-butyl-2-(4-cyanobenzylidene)hydrazinecarboxylate
• 英文别名: 4-cyanophenylcarbaldehyde-tert-butoxycarbonylhydrazone；tert-butyl N-[(4-cyanophenyl)methylideneamino]carbamate
• CAS: 149267-91-4
• 化学式: C₁₃H₁₅N₃O₂
• 分子量: 245.281
• InChiKey: VBPCBEWYAWBIRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl-2-(4-cyanobenzylidene)hydrazinecarboxylate 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以90%的产率得到N′-[chloro-(4-cyanophenyl)methylene]-tert-butylcarbazate
  参考文献：
  名称：

  Synthesis of 5-aryl-3H-[1,3,4]oxadiazol-2-ones from N′-(chloro-aryl-methylene)-tert-butylcarbazates using basic alumina as an efficient and recyclable surface under solvent-free condition

  摘要：

  The synthesis of biologically important 5-aryl-3H-[1,3,4]oxadiazol-2-ones has been carried out by heating the easily synthesized N'-(chloro-aryl-methylene)-tert-butylcarbazates on basic alumina surface under solvent-free condition. The dual characteristic of basic alumina as a solid support as well as a nucleophile is successfully exploited in these reactions. The method provides special attributions such as reduced reaction times, easier work-up procedures, and good to excellent yields as well as increased purity of products and most importantly environmentally friendly protocols. The basic alumina is easily recovered and utilized for further reactions several times without serious loss of activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.128
• 作为产物：
  描述：

  4-氰基苯甲醛 以 乙醇 为溶剂， 生成 tert-butyl-2-(4-cyanobenzylidene)hydrazinecarboxylate
  参考文献：
  名称：

  Antiretroviral hydrazine derivatives

  摘要：

  本发明涉及具有公式##STR1##的化合物及其盐、药物组合物、中间体及其制备方法。

  公开号：

  US05753652A1

文献信息

• Design and structure–activity relationship of thrombin inhibitors with an azaphenylalanine scaffold: potency and selectivity enhancements via P2 optimization
  作者：A Zega、G Mlinšek、P Šepic、S Golič Grdadolnik、T Šolmajer、T.B Tschopp、B Steiner、D Kikelj、U Urleb

  DOI：10.1016/s0968-0896(01)00202-4

  日期：2001.10

  provides an enhanced fit into this active site S2 pocket. In the present paper, we also report on the structure of these inhibitors in solution and conformational analysis of inhibitors in the active site in order to asses the consequences of the replacement of the central alpha-CH by a nitrogen functionality. In vitro biological testing of the designed inhibitors shows that elimination of R, S stereoisomerism

  理论和结构研究，然后进行定向合成和体外生物学测试，使我们获得了新型的非共价凝血酶假肽抑制剂。我们已经将氮杂肽支架整合到经典三肽D-Phe-Pro-Arg抑制剂结构的中心部分，从而从分子中消除了一个立体定位中心。设计了一系列化合物以优化凝血酶S2口袋的占用率。在P2处增加的疏水性增强了对该活性位点S2口袋的贴合性。在本文中，我们还报告了这些抑制剂在溶液中的结构以及活性位点中抑制剂的构象分析，以评估氮官能团取代中心α-CH的后果。
• The continuous-flow synthesis of carbazate hydrazones using a simplified computer-vision controlled liquid–liquid extraction system
  作者：Matthew O’Brien、Dennis A. Cooper、Panashe Mhembere

  DOI：10.1016/j.tetlet.2016.10.018

  日期：2016.11

  A computer-vision controlled liquid–liquid extraction system was used in the continuous-flow synthesis of a series of carbazate hydrazones. The system uses open-source software components (Python, OpenCV) and is simpler and potentially more economical, in terms of hardware, than one we have described previously.

  计算机视觉控制的液-液萃取系统用于一系列氨基甲酸酯的连续流合成。该系统使用开源软件组件（Python，OpenCV），并且在硬件方面比我们先前描述的更为简单，并且可能更经济。
• Thrombin inhibitors built on an azaphenylalanine scaffold
  作者：Anamarija Zega、Gregor Mlinšek、Tomaž Šolmajer、Alenka Trampuš-Bakija、Mojca Stegnar、Uroš Urleb

  DOI：10.1016/j.bmcl.2003.12.083

  日期：2004.3

  A series of azaphenylalanine derivatives were investigated as novel thrombin inhibitors based on the prodrug principle. By systematic structural modifications we have identified optimal groups for this series that led us to potent inhibitors of thrombin incorporating the benzamidine fragment at the PI position, and their potentially orally active benzamidoxime prodrugs. The binding modes in the thrombin active site of two representative compounds were identified by X-ray crystallographic analysis. (C) 2004 Published by Elsevier Ltd.