1-(2-methoxy-2-oxoethyl)-3,5-dimethylpyridin-1-ium bromide

• 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: 1-(2-methoxy-2-oxoethyl)-3,5-dimethylpyridin-1-ium bromide
• 英文别名: Methyl 2-(3,5-dimethylpyridin-1-ium-1-yl)acetate;bromide
• 化学式: Br*C₁₀H₁₄NO₂
• 分子量: 260.131
• InChiKey: AVYPYOGLIYINGK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.23
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-methoxy-2-oxoethyl)-3,5-dimethylpyridin-1-ium bromide 在 三乙胺 、 三氯化磷 作用下， 以 甲苯 为溶剂， 以71%的产率得到
  参考文献：
  名称：

  Pyridinium dichlorophosphinomethylides

  摘要：

  AbstractSeven new pyridinium dichlorophosphinomethylides 2 have been obtained from dichlorophosphinylation of the pyridinium methylides generated in situ. 2 give 1,3‐bis(alkoxycarbonyl)‐2‐phosphaindolizines 4 through 1,5‐electrocyclization of the intermediate, bis(pyridinium ylidyl)phosphenium chloride 3 which is generated either from disproportionation of 2 or from the reaction of 2 with pyridinium methylide. Formation of 3 has been confirmed by carrying out a crossed reaction. 3‐Substituted 2 forms 4 regiospecifically. Intramolecular 1,5‐cyclocondensation of 2‐methylpyridinium dichlorophosphinomethylide is preferred over its disproportionation. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:602–609, 2001

  DOI：

  10.1002/hc.1091
• 作为产物：
  描述：

  3,5-二甲基吡啶 、 溴乙酸甲酯 以 乙醚 为溶剂， 反应 24.0h， 以38%的产率得到1-(2-methoxy-2-oxoethyl)-3,5-dimethylpyridin-1-ium bromide
  参考文献：
  名称：

  1,3-偶极吡啶鎓叶立德与电子缺陷型酰胺的环加成反应合成2-氨基吲哚并嗪

  摘要：

  具有炔酸或炔酮部分的电子不足的酰胺，已首次成功地与稳定的吡啶鎓碘化物进行1,3-偶极环加成反应。这些反应为各种取代的2-氨基吲哚嗪提供了有效且普遍的途径，这些取代的2-氨基吲哚嗪可以用作合成其他更复杂的氮杂环的有用前体。

  DOI：

  10.1021/acs.orglett.5b01205

文献信息

• 2-Phosphaindolizines via 1,5-electrocyclization
  作者：Raj K. Bansal、Anushka Surana、Neelima Gupta

  DOI：10.1016/s0040-4039(98)02645-8

  日期：1999.2

  N-Pyridinium dichlorophosphinomethylides disproportionate to generate bis(N-pyridinium ylidyl)phosphenium chloride which undergoes 1,5-electrocyclization to give 2-phosphaindolizines. In one-pot synthesis N-(alkoxycarbonylmethyl)pyridinium bromide reacts with PCl3 in presence of Et3N to form 2-phosphaindolizine.

  N-吡啶二氯膦基甲基化物不成比例生成氯化双（N-吡啶基吡啶基）phosph，将其进行1,5-电环化生成2-膦基吲哚酮。在一锅法合成中，N-（烷氧基羰基甲基）吡啶鎓溴化物在Et 3 N存在下与PCl 3反应形成2-磷酸吲哚嗪。
• Synthesis of 2-Aminoindolizines by 1,3-Dipolar Cycloaddition of Pyridinium Ylides with Electron-Deficient Ynamides
  作者：Julien Brioche、Christophe Meyer、Janine Cossy

  DOI：10.1021/acs.orglett.5b01205

  日期：2015.6.5

  possessing an ynoate or an ynone moiety, have been successfully involved for the first time in a 1,3-dipolar cycloaddition with stabilized pyridinium ylides. These reactions afford an efficient and general access toward a variety of substituted 2-aminoindolizines which can serve as useful precursors for the synthesis of other more complex nitrogen heterocycles.

  具有炔酸或炔酮部分的电子不足的酰胺，已首次成功地与稳定的吡啶鎓碘化物进行1,3-偶极环加成反应。这些反应为各种取代的2-氨基吲哚嗪提供了有效且普遍的途径，这些取代的2-氨基吲哚嗪可以用作合成其他更复杂的氮杂环的有用前体。
• Pyridinium dichlorophosphinomethylides
  作者：Raj K. Bansal、Neelima Gupta、Mukta Baweja、Leena Hemrajani、Vimal K. Jain

  DOI：10.1002/hc.1091

  日期：——

  AbstractSeven new pyridinium dichlorophosphinomethylides 2 have been obtained from dichlorophosphinylation of the pyridinium methylides generated in situ. 2 give 1,3‐bis(alkoxycarbonyl)‐2‐phosphaindolizines 4 through 1,5‐electrocyclization of the intermediate, bis(pyridinium ylidyl)phosphenium chloride 3 which is generated either from disproportionation of 2 or from the reaction of 2 with pyridinium methylide. Formation of 3 has been confirmed by carrying out a crossed reaction. 3‐Substituted 2 forms 4 regiospecifically. Intramolecular 1,5‐cyclocondensation of 2‐methylpyridinium dichlorophosphinomethylide is preferred over its disproportionation. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:602–609, 2001