N-(4-nitro-phenyl)-N-nitroso-glycine | 69978-02-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(4-nitro-phenyl)-N-nitroso-glycine
• 英文别名: N-(4-Nitro-phenyl)-N-nitroso-glycin；N-nitroso-N-(4-nitrophenyl)glycine；2-(4-nitro-N-nitrosoanilino)acetic acid
• CAS: 69978-02-5
• 化学式: C₈H₇N₃O₅
• 分子量: 225.161
• InChiKey: CFPNDRJAKMEUIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(4-nitro-phenyl)-N-nitroso-glycine 在 三氟乙酸酐 作用下， 以 neat (no solvent) 为溶剂， 反应 0.5h， 生成 3-(4-硝基苯基)-1,2,3-恶二唑-3-鎓-5-醇
  参考文献：
  名称：

  铜催化的Sydnone-炔烃环加成反应由芳基甘氨酸一锅法合成1,4-二取代吡唑

  摘要：

  利用铜催化的sydnone-炔烃环加成反应，开发了一种从芳基甘氨酸构建1,4-吡唑的可靠方法。该程序通过三步一锅法为吡唑杂环提供了一条简单而通用的途径。

  DOI：

  10.1021/jo501420r
• 作为产物：
  描述：

  2-(4-硝基苯基氨基)乙酸 在 亚硝酸特丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 N-(4-nitro-phenyl)-N-nitroso-glycine
  参考文献：
  名称：

  4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne

  摘要：

  4-卤代-悉尼酮被发现是双环[6.1.0]-壬炔进行应变促进点击反应的高效偶极伙伴。这种生物正交反应已被应用于蛋白质标记。

  DOI：

  10.1039/c4cc03816a

文献信息

• Syntheses of heterocyclic compounds. Part XVIII. Aminolysis of 3-aryl-4-bromosydnones, and acid hydrolysis of 3-arylsydnoneimines
  作者：G. S. Puranik、H. Suschitzky

  DOI：10.1039/j39670001006

  日期：——

  various 3-aryl- and 3-heteroaryl-4-bromosydnones with piperidine gives the corresponding piperidino-glycyl-piperidines. Fluorine labelling has confirmed the postulated course of fission induced by acids in 3-aryl-sydnoneimines.

  各种3-芳基-和3-杂芳基-4-溴代壬烯与哌啶的反应得到相应的哌啶子基-缩水甘油基-哌啶。氟标记已经证实了由酸在3-芳基-亚砜亚胺中诱导的裂变过程。
• One-Pot Synthesis of 1,4-Disubstituted Pyrazoles from Arylglycines via Copper-Catalyzed Sydnone–Alkyne Cycloaddition Reaction
  作者：Simon Specklin、Elodie Decuypere、Lucie Plougastel、Soifia Aliani、Frédéric Taran

  DOI：10.1021/jo501420r

  日期：2014.8.15

  method for constructing 1,4-pyrazoles from arylglycines was developed using the copper-catalyzed sydnone–alkyne cycloaddition reaction. The procedure offers a straightforward and general route to the pyrazole heterocycle through a three-step one-pot procedure.

  利用铜催化的sydnone-炔烃环加成反应，开发了一种从芳基甘氨酸构建1,4-吡唑的可靠方法。该程序通过三步一锅法为吡唑杂环提供了一条简单而通用的途径。
• Microwave-assisted Synthesis of N-Arylglycines: Improvement of Sydnone Synthesis
  作者：Davood Azarifar、Hassan Ghasemnejad Bosra、Mohammad-Ali Zolfigol、Mahmood Tajbaksh

  DOI：10.3987/com-05-10574

  日期：——

  Reactions of anilines with ethyl bromoacetate under microwave irradiation have afforded N-arylglycines that are subsequently converted to their N-nitroso derivatives with a combination of silica chloride or periodic acid, wet SiO2 and sodium nitrite in CH2Cl2 with satisfactory yields. In the final step, the use of 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a new and effective reagent for dehydration of N-nitroso-N-arylglycines to sydnones was successfully examined.
• Synthesis of 2<i>H</i>-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes
  作者：Yuesi Fang、Chunrui Wu、Richard C. Larock、Feng Shi

  DOI：10.1021/jo201605v

  日期：2011.11.4

  A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields this protocol, and subsequent Pd-catalyzed coupling reactions can be applied to the halogenated products to generate a structurally diverse library of indazoles.
• Raman spectra of SiC nanorods with different excitation wavelengths
  作者：Yan Yan、Fumin Huang、Shulin Zhang、Bangfen Zhu、Eryi Shang、Shoushan Fan

  DOI：10.1007/bf02901158

  日期：2001.11

  With increasing excitation wavelength from 514 to 782 mn, a significant difference in the Raman spectra of SIC nanorods was observed as compared to bulk material. The intensity ratio of the LO mode to that of the IF mode increases with the excitation wavelength increasing. This has been identified as resonant Raman scattering caused by Frohlich interaction.