3-benzoyl-1-methoxycarbonylindolizine-5-carbaldehyde | 135489-62-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-1-methoxycarbonylindolizine-5-carbaldehyde
• 英文别名: Methyl 3-benzoyl-5-formylindolizine-1-carboxylate
• CAS: 135489-62-2
• 化学式: C₁₈H₁₃NO₄
• 分子量: 307.306
• InChiKey: GWBHNZVSCFIJNC-UHFFFAOYSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzoyl-1-methoxycarbonylindolizine-5-carbaldehyde 在 sodium cyanoborohydride 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 trimethyl 14-methyl-12-phenyl-13,14-diazatetracyclo[6.4.1.19,12.04,13]tetradeca-1,3,5,7,10-pentaene-3,10,11-tricarboxylate
  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：

  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-methoxycarbonylindolizine-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

文献信息

• Novel synthetic routes to nitrogen-bridged tricyclic derivatives of pyrrolo[2,1,5-cd]indolizine and pyrrolo[2,1,5-de]quinolizine derived from 2-acyl-N-(acylmethyl)pyridinium halides
  作者：Jiaxin Hu、Xin Jiang、Ting He、Jian Zhou、Yuefei Hu、Hongwen Hu

  DOI：10.1039/b102449n

  日期：——

  routes to nitrogen-bridged derivatives of pyrrolo[2,1,5-cd]indolizine and pyrrolo[2,1,5-de]quinolizine were developed starting from 2-acyl-N-(acylmethyl)pyridinium halides. Thus, 2-benzoyl-N-phenacylpyridinium bromide (1) afforded 3,4-diphenylpyrrolo[2,1,5-cd]indolizines (4) via 1,3-dipolar cycloaddition, to yield 3,5-dibenzoylindolizines (3), followed by intramolecular McMurry coupling. Similarly

  氮的桥联衍生物的新型合成路线 pyrrolo [2,1,5- cd ]吲哚利嗪 和 吡咯并[2,1,5- de ]喹诺嗪从2-酰基-N-（酰基甲基）吡啶鎓卤化物开始研发。因此，2-苯甲酰基-N-苯甲酰吡啶鎓溴化物（1），得到3,4-二苯基[2,1,5- CD ]中氮茚（4）通过 1,3-偶极环加成，得到3，5-二苯甲酰吲哚并咪唑（3），随后进行分子内McMurry偶联。相似地，2-（1,3-二氧戊环-2-基）-N-苯甲酰吡啶鎓溴化物（5）给3-苯基吡咯并[2,1,5- cd ]吲哚嗪（7）与意外的产物3-苯基-4-羟基吡咯并[2,1,5- cd ]吲哚并嗪（8）。然而，2-乙酰基-N-苯甲酰吡啶鎓溴化物 （13）或2-苯甲酰基-N-丙酮基溴化吡啶鎓（16）发生了串联反应。醛醇缩合 和 1,3-偶极环加成形成3-苯基-5 H-吡咯并[2,1,5- de ]喹啉嗪-5-酮（15）或5-苯基-3
• 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).