1,2,4-三甲氧基-5-(2-硝基乙烯基)苯 | 24160-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1,2,4-三甲氧基-5-(2-硝基乙烯基)苯
• 英文名称: Benzene, 1,2,4-trimethoxy-5-(2-nitroethenyl)-
• 英文别名: 1,2,4-trimethoxy-5-(2-nitroethenyl)benzene
• CAS: 24160-51-8
• 化学式: C₁₁H₁₃NO₅
• mdl: MFCD00297718
• 分子量: 239.228
• InChiKey: DPZJDIXHUBSWDS-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿、DCM、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2,4-三甲氧基-5-(2-硝基乙烯基)苯 在 sodium azide 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2,4,5-trimethoxyphenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles

  摘要：

  Aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to 2-cycloalken-1-ones has been studied in the presence of DABCO as organic base. The reactions were carried out in acetonitrile at room temperature to provide 2,4-disubstituted 2H-1,2,3-triazoles as major adducts and 1,4-disubstituted 1H-1,2,3-triazoles as minor adducts. Though the reaction times are longer (4-8 days), the two regioisomers were separated by using column chromatography and the adducts were obtained in very good to excellent combined chemical yields. The electron-rich and electron-poor substituents on aryl moiety of 4-aryl-triazoles could tolerate the reaction conditions to afford the title adducts. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.11.125

文献信息

• Effect of Sulfamic Acid on 1,3-Dipolar Cycloaddition Reaction: Mechanistic Studies and Synthesis of 4-Aryl-NH-1,2,3-triazoles from Nitroolefins
  作者：Pankaj Sharma、Niggula Kumar、Kishna Senwar、Oscar Forero-Doria、Fabiane Nachtigall、Leonardo Santos、Nagula Shankaraiah

  DOI：10.21577/0103-5053.20160203

  日期：——

  A facile and new metal-free 1,3-dipolar cycloaddition reaction for the synthesis of 4-aryl-NH-1,2,3-triazoles from nitroolefins and NaN3 employing NH2SO3H has been developed. Sulfamic acid proved to be an efficient additive in this transformation by inhibiting the formation of triaryl benzene. Mechanistic aspects and key intermediates associated with this transformation have also been characterized

  已经开发了一种简便且无金属的1,3-偶极环加成反应，该反应可使用NH2SO3H由硝基烯烃和NaN3合成4-芳基-NH-1,2,3-三唑。通过抑制三芳基苯的形成，氨基磺酸被证明是该转化过程中的有效添加剂。通过使用电喷雾电离串联质谱法（ESI-MS / MS）在线监测反应，也可以表征与该转化有关的机理方面和关键中间体。该协议强调了广泛的底物范围，可用于多种功能，简单的反应条件，例如对露天的稳定性，更少的反应时间，易于后处理，生态友好且产率高至优异。
• DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles
  作者：Ujjawal Kumar Bhagat、Kamaluddin、Rama Krishna Peddinti

  DOI：10.1016/j.tetlet.2016.11.125

  日期：2017.1

  Aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to 2-cycloalken-1-ones has been studied in the presence of DABCO as organic base. The reactions were carried out in acetonitrile at room temperature to provide 2,4-disubstituted 2H-1,2,3-triazoles as major adducts and 1,4-disubstituted 1H-1,2,3-triazoles as minor adducts. Though the reaction times are longer (4-8 days), the two regioisomers were separated by using column chromatography and the adducts were obtained in very good to excellent combined chemical yields. The electron-rich and electron-poor substituents on aryl moiety of 4-aryl-triazoles could tolerate the reaction conditions to afford the title adducts. (C) 2016 Elsevier Ltd. All rights reserved.