1-phenacyl-2-(1,3-dioxolan-2-yl)pyridinium bromide | 135489-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenacyl-2-(1,3-dioxolan-2-yl)pyridinium bromide
• 英文别名: 2-[2-(1,3-Dioxolan-2-yl)pyridin-1-ium-1-yl]-1-phenylethanone;bromide
• CAS: 135489-59-7
• 化学式: Br*C₁₆H₁₆NO₃
• 分子量: 350.212
• InChiKey: MRWKNZSHUNYIMM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.09
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-phenacyl-2-(1,3-dioxolan-2-yl)pyridinium bromide 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 3-benzoyl-1,2-dimethoxybonylindolizine-5-carbaldehyde
  参考文献：
  名称：

  A New Entry to [2.3.4]Cyclazines

  摘要：

  Treatment of 2,3-dihydro-2-methyl-3-phenyl-1H-pyrazino[3,4,5-cd]indolizine 2-oxides (5) with trifluoroacetic anhydride gave new heterocyclic six-membered betaines (6) which underwent 1,3-dipolar cycloaddition reaction with dimethyl acetylenedicarboxylate and maleimides in hot toluene to yield the corresponding cycloadducts (7) and (8). Treatment of the maleimide adducts (8) with p-toluenesulfonic acid in boiling acetic acid gave the [2.3.4]cyclazines (9).

  DOI：

  10.3987/com-91-5665
• 作为产物：
  描述：

  2-(1,3-二氧杂烷-2-基)吡啶 、 2-溴苯乙酮 以 乙腈 为溶剂， 以90%的产率得到1-phenacyl-2-(1,3-dioxolan-2-yl)pyridinium bromide
  参考文献：
  名称：

  A New Entry to [2.3.4]Cyclazines

  摘要：

  Treatment of 2,3-dihydro-2-methyl-3-phenyl-1H-pyrazino[3,4,5-cd]indolizine 2-oxides (5) with trifluoroacetic anhydride gave new heterocyclic six-membered betaines (6) which underwent 1,3-dipolar cycloaddition reaction with dimethyl acetylenedicarboxylate and maleimides in hot toluene to yield the corresponding cycloadducts (7) and (8). Treatment of the maleimide adducts (8) with p-toluenesulfonic acid in boiling acetic acid gave the [2.3.4]cyclazines (9).

  DOI：

  10.3987/com-91-5665

文献信息

• A Convenient Synthesis of 3-Benzoylindolizine-5-carbaldehydes
  作者：J. Zhou、Y. Hu、H. Hu

  DOI：10.1080/00397919808004447

  日期：1998.9

  3-Benzoylindolizine-5-carbaldehydes (4a-f), which could be used as derivatization reagents for amino compounds in HPCE were synthesized based on the 1,3-dipolar cycloaddition of 1-phenacyl-2-(1,3-dioxolan-2-yl)pyridinium ylide with alkenes in the presence of TPCD.
• A New Entry to [2.3.4]Cyclazines
  作者：Yasuyoshi Miki、Hiroko Hachiken、Masami Yoshikawa、Shoji Takemura

  DOI：10.3987/com-91-5665

  日期：——

  Treatment of 2,3-dihydro-2-methyl-3-phenyl-1H-pyrazino[3,4,5-cd]indolizine 2-oxides (5) with trifluoroacetic anhydride gave new heterocyclic six-membered betaines (6) which underwent 1,3-dipolar cycloaddition reaction with dimethyl acetylenedicarboxylate and maleimides in hot toluene to yield the corresponding cycloadducts (7) and (8). Treatment of the maleimide adducts (8) with p-toluenesulfonic acid in boiling acetic acid gave the [2.3.4]cyclazines (9).