3-(4-methoxycarbonyl)phenylsydnone | 89101-10-0

• 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: 3-(4-methoxycarbonyl)phenylsydnone
• 英文别名: 3-(4-(methoxycarbonyl)phenyl)-1,2,3-oxadiazol-3-ium-5-olate；3-[4-(Methoxycarbonyl)phenyl]sydnone；3-(4-methoxycarbonylphenyl)oxadiazol-3-ium-5-olate
• CAS: 89101-10-0
• 化学式: C₁₀H₈N₂O₄
• 分子量: 220.185
• InChiKey: UVOJYCBMTLEJIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-methoxycarbonyl)phenylsydnone 在 硫酸 、 溴 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 9.0h， 生成 2-[4-(5-mercapto[1,3,4]oxadiazol-2-yl)phenyl]-5-methyl-4-[(thiazol-4-ylmethylene)-amino]-2,4-dihydro[1,2,4]triazol-3-one
  参考文献：
  名称：

  Synthesis of some novel 1,2,4-triazole and 1,3,4-oxadiazole derivatives of biological interest

  摘要：

  In this study, a series of novel [1,2,4]-triazolo-[1,3,4]oxadiazole (8), [1,2,4]-triazolo-[1,3,4]oxadiazole thioethers (9a-b), [1,2,4]-triazolo-[1,3,4]oxadiazole arylidines (10a-g), and bis[1,2,4]-triazole (11) derivatives were prepared with the objective of developing better antimicrobial activity. The structures of the compounds were elucidated by spectral analysis. The newly synthesized compounds (8), (9a-b), (10a-g), and (11) were screened for their antimicrobial activity. Among all the tested compounds (10b) shows significant antibacterial activity.

  DOI：

  10.1007/s00044-012-0332-3
• 作为产物：
  描述：

  {[4-(methoxycarbonyl)phenyl](nitroso)amino}acetic acid 在 乙酸酐 作用下， 以86%的产率得到3-(4-methoxycarbonyl)phenylsydnone
  参考文献：
  名称：

  3-[4-(烷氧基羰基)苯基]sydnones及其衍生物的合成与生物活性

  摘要：

  合成了四种新的 3-[4-（烷氧基羰基）苯基] sydnones。酰肼4与各种芳香醛缩合得到相应的席夫碱。sydnones 和一些船舶基地的抗菌活性已被报道。讨论了 3 [4-（乙氧羰基）苯基] sydnone 的质谱碎片。

  DOI：

  10.1002/ardp.19843170112

文献信息

• Accelerated Discovery in Photocatalysis by a Combined Screening Approach Involving MS Tags
  作者：Michael Teders、Sabrina Bernard、Karin Gottschalk、J. Luca Schwarz、Eric A. Standley、Elodie Decuypere、Constantin G. Daniliuc、Davide Audisio、Frédéric Taran、Frank Glorius

  DOI：10.1021/acs.orglett.9b03936

  日期：2019.12.6

  on the development of an MS tag screening strategy that accelerates the discovery of photocatalytic reactions. By efficiently combining mechanism- and reaction-based screening dimensions, the respective advantages of each strategy were retained, whereas the drawbacks inherent to each screening approach could be eliminated. Applying this approach led to the discovery of a mild photosensitized decarboxylative

  在本文中，我们报告了MS标签筛选策略的发展，该策略可加快光催化反应的发现。通过有效地组合基于机理和基于反应的筛选维度，可以保留每种策略各自的优点，而可以消除每种筛选方法固有的缺点。应用该方法导致发现了由中离子的sydnones和羧酸作为起始原料合成的温和的光敏脱羧酰肼的合成方法。
• Transformation of the sydnone ring into oxadiazolinones. A convenient one-pot synthesis of 3-aryl-5-methyl-1,3,4-oxadiazolin-2-ones from 3-arylsydnones and their antimicrobial activity
  作者：Shanta G Mallur、Bharati V Badami

  DOI：10.1016/s0014-827x(99)00103-2

  日期：2000.1

  4-oxadiazolin-2-ones (IIIa-u) by a single-step reaction with bromine in acetic anhydride. In the preliminary screening of all these compounds, the halogen-substituted derivatives have shown antimicrobial activities equal to those of the standard drugs used.

  通过与溴在乙酸酐中的一步反应，将3-芳基sydnones（Ia-u）转化为相应的3-芳基-5-甲基-1,3,4-恶二唑啉-2-酮（IIIa-u）。在所有这些化合物的初步筛选中，卤素取代的衍生物已显示出与所用标准药物相同的抗微生物活性。
• Copper-catalyzed chemoselective synthesis of 4-trifluoromethyl pyrazoles
  作者：Jiaqing Lu、Yuning Man、Yabin Zhang、Bo Lin、Qi Lin、Zhiqiang Weng

  DOI：10.1039/c9ra07694h

  日期：——

  of 4-trifluoromethyl pyrazoles have been prepared via the copper-catalyzed cycloaddition of 2-bromo-3,3,3-trifluoropropene with a variety of N-arylsydnone derivatives under mild conditions. This new protocol under optimized reaction conditions [Cu(OTf)2/phen, DBU, CH3CN, 35 °C] afforded 4-trifluoromethyl pyrazoles in moderate to excellent yields with excellent regioselectivity.

  在温和条件下，通过铜催化的 2-bromo-3,3,3-trifluoropropene 与多种N -arylsydnone 衍生物的环加成反应制备了一系列 4-三氟甲基吡唑。这种在优化反应条件 [Cu(OTf) 2 /phen, DBU, CH 3 CN, 35 °C] 下的新方案以中等至优异的产率和优异的区域选择性提供了 4-三氟甲基吡唑。
• A zinc-catalyzed synthesis of 3-trifluoromethyl-4-trifluoroacetyl pyrazoles
  作者：Biqiong Hong、Xinzhi Ding、Mengfan Jiang、Lu Qin、Zitong Lin、Wei Wu、Zhiqiang Weng

  DOI：10.1016/j.tetlet.2022.154018

  日期：2022.8

  and general method for the synthesis of 3-trifluoromethyl-4‑trifluoroacetyl pyrazoles from the cycloaddition of sydnones with 1,1,1,5,5,5-hexafluoropentane-2,4-dione has been established. Using ZnI2/bpy as a catalyst in THF, this protocol proved to be general to prepare a variety of 3-trifluoromethyl-4‑trifluoroacetyl pyrazoles in good yields. Utility of this method was demonstrated by further transformations

  建立了一种有效且通用的方法，用于通过 1,1,1,5,5,5-六氟戊烷-2,4-二酮环加成合成 3-三氟甲基-4-三氟乙酰基吡唑。使用 ZnI 2 /bpy 作为 THF 中的催化剂，该方案被证明可以以良好的收率制备各种 3-三氟甲基-4-三氟乙酰基吡唑。该方法的实用性通过三氟乙酰基的进一步转化证明了该方法的实用性，提供了方便地获得基于 3-三氟甲基吡唑的羧酸和醇衍生物的途径。
• Regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles <i>via</i> photocycloaddition of sydnone with CF₃CN
  作者：Bo Lin、Yunfei Yao、Yangjie Huang、Qi Lin、Zhiqiang Weng

  DOI：10.1039/d2cc03928a

  日期：——

  A general and regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles has been achieved through photocycloaddition of sydnone with trifluoroacetonitrile. This method employed trifluoroacetaldehyde O-(aryl)oxime as the CF3CN precursor and tolerated various functional groups to furnish 3-trifluoromethyl 1,2,4-triazole products in moderate to good yields. Mechanistic experiments revealed an energy

  3-三氟甲基 1,2,4-三唑的通用和区域选择性合成是通过 sydnone 与三氟乙腈的光环加成反应实现的。该方法使用三氟乙醛O- (芳基)肟作为 CF 3 CN 前体并耐受各种官能团，以中等至良好的收率提供 3-三氟甲基 1,2,4-三唑产物。机械实验揭示了从光催化剂 4-CzIPN 到 sydnone 底物的能量转移。