ethyl 2-(p-fluorophenylcarbamoyl)hydrazine-1-carboxylate | 223401-28-3

• 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: ethyl 2-(p-fluorophenylcarbamoyl)hydrazine-1-carboxylate
• 英文别名: ethyl N-[(4-fluorophenyl)carbamoylamino]carbamate
• CAS: 223401-28-3
• 化学式: C₁₀H₁₂FN₃O₃
• 分子量: 241.222
• InChiKey: HRSKLKJNWNQRPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(p-fluorophenylcarbamoyl)hydrazine-1-carboxylate 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氯化锆(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 1-ethoxycarbonyl-4-(4-fluorophenyl)-2-(2,4,6-trimethoxyphenyl)semicarbazide
  参考文献：
  名称：

  ZrCl₄-Mediated Regioselective Electrophilic Amination of Activated Arenes with New Alkyl Arylaminocarbonyldiazenecarboxylates:  Intermolecular and Intramolecular Reactions

  摘要：

  DOI：

  10.1021/jo9821170
• 作为产物：
  描述：

  4-氟苯胺 在 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 生成 ethyl 2-(p-fluorophenylcarbamoyl)hydrazine-1-carboxylate
  参考文献：
  名称：

  One-pot and novel route for the synthesis of 4-substituted-1,2,4-triazolidine-3,5-diones

  摘要：

  The efficient and one-pot synthesis of 4-substituted-1,2,4-triazolidin-3,5-dione derivatives (4-substituted urazoles) via combination of triphosgene, substituted anilines, and ethyl carbazate in the presence of cesium carbonate is presented. (C) 2013 Arash Ghorbani-Choghamarani. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.11.020

文献信息

• Water‐Involved Ring‐Opening of 4‐Phenyl‐1,2,4‐triazoline‐3,5‐dione for “Photo‐Clicked” Access to Carbamoyl Formazan Photoswitches In Situ
  作者：Yuanqin Zheng、Yuqiao Zhou、Yan Zhang、Pengchi Deng、Xiaohu Zhao、Shichao Jiang、Guangxi Du、Xin Shen、Xinyu Xie、Zhishan Su、Zhipeng Yu

  DOI：10.1002/asia.202101239

  日期：2022.1.17

  The perishable nature of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) in aqueous medium is always considered as a side-effect. The rapid color fading of PTAD inspired us to explore the mechanism of its hydrolysis. Herein, photogenerated nitrile imine is discovered to be an ultra-fast trapping agent to “click” with a ring-opening hydrolysate with an umpolung effect, which resulted in an unprecedented

  4-苯基-1,2,4-三唑啉-3,5-二酮(PTAD) 在水性介质中易腐烂的性质始终被认为是一种副作用。PTAD 的快速褪色启发了我们探索其水解机制。在此，发现光生腈亚胺是一种超快速捕获剂，可与具有 umpolung 效应的开环水解产物“点击”，从而产生前所未有的氨基甲酰基甲臜作为光可切换键。
• Synthesis and anti-leishmanial activity of heterocyclic betulin derivatives
  作者：Sami Alakurtti、Tuomo Heiska、Alexandros Kiriazis、Nina Sacerdoti-Sierra、Charles L. Jaffe、Jari Yli-Kauhaluoma

  DOI：10.1016/j.bmc.2010.01.003

  日期：2010.2

  Betulin, a naturally occurring abundant triterpene is converted in four steps to 3,28-di-O-acetyllupa-12,18-diene. When various 4-substituted urazoles were oxidized to the corresponding urazines with iodobenzene diacetate in the presence of 3,28-di-O-acetyllupa-12,18-diene, new heterocyclic betulin derivatives were produced. These betulin derivatives were examined in a microplate assay at 50 μM for

  桦木素，一种天然存在的丰富的三萜，可通过四个步骤转化为3,28-二-O-乙酰基acetyl- 12,18-二烯。在3,28-二-O-乙酰基lu- 12,18-二烯的存在下，用碘代苯二乙酸酯将各种4-取代的脲唑氧化为相应的脲嗪时，会生成新的杂环桦木衍生物。在微孔板分析中以50μM的浓度检测了这些betulin衍生物对抑制致死性内脏利什曼病的物种Leishmania donovani axenic amastigotes的生长的能力。胃肠道50测定最有效化合物的浓度（50％生长抑制的浓度），并评估其对人巨噬细胞THP-1的细胞毒性。还检查了对在巨噬细胞中生长的杜氏乳酸杆菌的抗利什曼活性。3,28-二-O-乙酰基lupa- 12,18-二烯和4-甲基尿嘧啶之间的杂环加合物是最有效的衍生物，其 对杜氏乳酸链球菌的GI 50 = 8.9μM。
• Telescoped Oxidation and Cycloaddition of Urazoles to Access Diazacyclobutenes
  作者：Brock A. Miller、Chandima J. Narangoda、Thomas L. Johnson、Ryan D. Barata、Flavoris Belue、Erin E. Solomon、Alexis A. Bragg、Daniel C. Whitehead

  DOI：10.1021/acs.joc.2c00280

  日期：2022.6.3

  previous method to access the diazacyclobutene scaffold did not allow for modification of the substituent originating from the 1,2,4-triazoline-3,5-dione component. We have circumvented this challenge and expanded access to additional structural diversity of the scaffold. A telescoped urazole oxidation and Lewis acid-catalyzed cyclization provided R3-substituted diazacyclobutenes. Calcium hypochlorite-mediated

  我们以前访问二氮杂环丁烯支架的方法不允许修改源自 1,2,4-三唑啉-3,5-二酮成分的取代基。我们已经规避了这一挑战，并扩大了对脚手架额外结构多样性的访问。伸缩的乌拉唑氧化和路易斯酸催化的环化提供了 R 3取代的二氮杂环丁烯。次氯酸钙介导的乌拉唑氧化，随后 MgCl 2催化所得三唑啉二酮与硫代炔烃的环化促进了二氮杂环丁烯的形成，该二氮杂环丁烯在源自三唑啉二酮组分的R 3位置带有取代。
• Diazenedicarboxamides as inhibitors of d-alanine-d-alanine ligase (Ddl)
  作者：Andreja Kovač、Vita Majce、Roman Lenaršič、Sergeja Bombek、Julieanne M. Bostock、Ian Chopra、Slovenko Polanc、Stanislav Gobec

  DOI：10.1016/j.bmcl.2007.01.015

  日期：2007.4

  D-Alanine-D-alanine ligase (Ddl) catalyzes the biosynthesis of an essential bacterial peptidoglycan precursor D-alanyl-D-alanine and it represents an important target for development of new antibacterial drugs. A series of semicarbazides, aminocarbonyldiazenecarboxylates, diazenedicarboxamides, and hydrazinedicarboxamides was synthesized and screened for inhibition of DdlB from Escherichia coli. Compounds with good inhibitory activity were identified, enabling us to deduce initial structure-activity relationships. Thirteen diazenedicarboxamides were better inhibitors than D-cycloserine and some of them also possess antibacterial activity, which makes them a promising starting point for further development. (c) 2007 Elsevier Ltd. All rights reserved.
• Development of Biocompatible Ene-Ligation Enabled by Prenyl-Based β-Caryophyllene with Triazoline/Selectfluor under Physiological Conditions
  作者：Sheng Wang、Yuanyuan Li、Hongling Zhou、Li Wang、Rui Wang

  DOI：10.1021/acs.joc.2c00841

  日期：2022.7.1