(Z)-C-(3,4,5-trimethoxyphenyl)-N-methyl-nitrone | 631861-84-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-C-(3,4,5-trimethoxyphenyl)-N-methyl-nitrone
• 英文别名: (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone；N-methyl-1-(3,4,5-trimethoxyphenyl)methanimine oxide
• CAS: 631861-84-2；1037455-08-5
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: JGKLSENMOYWCLG-GHXNOFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-C-(3,4,5-trimethoxyphenyl)-N-methyl-nitrone 、 三氯乙腈 以 氘代氯仿 为溶剂， 反应 192.0h， 生成
  参考文献：
  名称：

  Synthesis of 5-trichloromethyl-Δ4-1,2,4-oxadiazolines and their rearrangement into formamidine derivatives

  摘要：

  A series of 5-trichloro-Delta(4)-1,2,4-oxadiazolines have been synthesised by 1,3-dipolar cycloaddition of nitrones to trichloroacetonitrile. These oxadiazolines rearrange into formamidine derivatives, via ring opening and a 1,2-aryl shift from carbon to the adjacent amino nitrogen. Both cycloaddition and rearrangement are facilitated when electron deficient nitriles and electron rich nitrones are used. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.04.012
• 作为产物：
  描述：

  N-甲基羟胺盐酸盐 、 3,4,5-三甲氧基苯甲醛 在 magnesium sulfate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 以75%的产率得到(Z)-C-(3,4,5-trimethoxyphenyl)-N-methyl-nitrone
  参考文献：
  名称：

  Synthesis of 5-trichloromethyl-Δ4-1,2,4-oxadiazolines and their rearrangement into formamidine derivatives

  摘要：

  A series of 5-trichloro-Delta(4)-1,2,4-oxadiazolines have been synthesised by 1,3-dipolar cycloaddition of nitrones to trichloroacetonitrile. These oxadiazolines rearrange into formamidine derivatives, via ring opening and a 1,2-aryl shift from carbon to the adjacent amino nitrogen. Both cycloaddition and rearrangement are facilitated when electron deficient nitriles and electron rich nitrones are used. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.04.012

文献信息

• Regio- and stereoselectivity of polar [2+3] cycloaddition reactions between (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone and selected (E)-2-substituted nitroethenes
  作者：Radomir Jasiński、Magda Ziółkowska、Oleh Demchuk、Agata Maziarka

  DOI：10.2478/s11532-014-0518-2

  日期：2014.5.1

  [2+3] Cycloaddition reactions of the highly reactive (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone with (E)-2-R-nitroethenes proceed under mild conditions and yield mixtures of stereoisomeric 2-methyl-3-(3,4,5-trimethoxyphenyl)-4-nitro-5-R-isoxazolidines. The effect of regiospecificity of the cycloadditions may be accounted for by the theory of electrophilicity indexes. Stereoselectivity, however, is determined by a compilation of steric and secondary orbital effects.

  摘要：高反应性的（Z）-C-(3,4,5-三甲氧基苯基)-N-甲基亚硝基甲烷与（E）-2-R-硝基乙烯发生[2+3]环加成反应，在温和条件下进行，产生立体异构体混合物2-甲基-3-(3,4,5-三甲氧基苯基)-4-硝基-5-R-异氧杂环己烷。环加成的位置特异性效应可以通过亲电指数理论来解释。然而，立体选择性由立体和二次轨道效应的综合决定。