3-benzoyl-2-phenylindolizine-1-carbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-2-phenylindolizine-1-carbaldehyde
• 化学式: C₂₂H₁₅NO₂
• 分子量: 325.367
• InChiKey: YIYJMVWSDOVBLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴苯乙酮 在 potassium dichromate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-benzoyl-2-phenylindolizine-1-carbaldehyde
  参考文献：
  名称：

  One-pot synthesis of indolizine via 1,3-dipolar cycloaddition using a sub-equivalent amount of K₂Cr₂O₇ as an efficient oxidant under base free conditions

  摘要：

  X = 氯或溴；EWG1，EWG2 = 电子吸引基团，一锅法反应，29个例子，产率从中等到高，克级放大潜力得到确认。

  DOI：

  10.1039/c5ra06019b

文献信息

• Copper acetate monohydrate: a cheap but efficient oxidant for synthesizing multi-substituted indolizines from pyridinium ylides and electron deficient alkenes
  作者：Huayou Hu、Junjun Feng、Yulan Zhu、Ning Gu、Yuhe Kan

  DOI：10.1039/c2ra21213g

  日期：——

  We report a highly practical one-pot method for synthesizing multi-substituted indolizines from α-halide carbonyl compounds, pyridines and electron deficient alkenes in the presence of copper acetate monohydrate and sodium acetate in DMF. A variety of function groups are tolerable in standard reaction conditions, including aldehyde. 36 examples were presented. The yield of indolizine was from moderate to high. Furthermore, multi-substituted indolizines can be prepared at gram scale by this method.

  我们报道了一种高度实用的、一步合成多取代吲哚嗪的方法，该方法使用α-卤代羰基化合物、吡啶和缺电子烯烃，在醋酸铜一水合物和醋酸钠的DMF溶液中进行。在标准反应条件下，各种功能团（包括醛）都能耐受。我们提供了36个例子，吲哚嗪的产率从中等到高。此外，通过这种方法还能在克级规模上制备多取代吲哚嗪。
• Iodine-mediated one-pot synthesis of C-3 acylated indolizines from pyridines, aryl methyl ketones and acrylate derivatives
  作者：Youlai Fang、Lisheng He、Weidong Pan、Yuzhu Yang

  DOI：10.1016/j.tet.2019.05.058

  日期：2019.7

  reaction from pyridines, aryl methyl ketones and electron deficient acrylates has been accomplished in a “one-pot” manner, which provides a straightforward and efficient access to C-3 acylated indolizines. The key intermediate of N-ylides is hypothesized to be generated in situ from pyridines and (hetero)aryl methyl ketones in the presence of iodine. This method has been applied in the synthesis of two

  由吡啶，芳基甲基酮和缺乏电子的丙烯酸酯进行的I 2 / CuI促进的多组分反应已通过“一锅法”完成，可直接有效地获得C-3酰化的吲哚嗪。假设N-基团的关键中间体是在碘存在下由吡啶和（杂）芳基甲基酮原位生成的。该方法已应用于合成具有抗惊厥和抗炎活性的两个分子。
• General and Direct Synthesis of Indolizine-1-carbaldehydes by 1,3-Dipolar Cycloaddition of Phenylpropiolaldehyde with Pyridinium Ylides
  作者：Tao Gao、Xiuling Chen、Longqiang Jiang、Minghu Wu、Haibing Guo、Jian Wang、Shaofa Sun、Jeremy Oiler、Yalan Xing

  DOI：10.1002/ejoc.201600945

  日期：2016.10

  An efficient and one-step synthesis of indolizine-1-carbaldehydes from phenylpropiolaldehyde and pyridinium ylides was developed. The elegant methodology afforded functionalized indolizines with easy operation under mild reaction conditions and with wide substrate scope.

  开发了一种从苯丙醛和吡啶鎓叶立德高效一步合成 indolizine-1-carbaldehydes 的方法。优雅的方法提供了功能化的吲哚嗪，在温和的反应条件下易于操作，底物范围广。
• A Convenient Synthesis Of 1-Acyl Indolizines by 1,3-Dipolar Cycloaddition Reactions of Pyridinium Ylides and α,β-Unsaturated Aldehydes or Ketones in the Presence of Tetrakis-Pyridine Cobalt Dichromate
  作者：Xuechun Zhang、Weili Cao、Xudong Wei、Hongwen Hu

  DOI：10.1080/00397919708006070

  日期：1997.4

  Abstract In the presence of tetrakispyridine cobalt dichromate (CoPy4(HCrO4)2), pyridinium ylides and α,β-unsaturated aldehydes or ketones undergo 1,3-dipolar cycloaddition reactions followed by in situ aromatization to give 1-acyl substituted indolizines in moderate to good yields.

  摘要 在四吡啶重铬酸钴 (CoPy4(HCrO4)2) 存在下，吡啶鎓叶立德和 α,β-不饱和醛或酮发生 1,3-偶极环加成反应，然后原位芳构化，得到 1-酰基取代的吲哚茚。良好的收益。
• One-pot synthesis of indolizine via 1,3-dipolar cycloaddition using a sub-equivalent amount of K₂Cr₂O₇ as an efficient oxidant under base free conditions
  作者：Chao Wang、Huayou Hu、Juanfang Xu、Weiqiu Kan

  DOI：10.1039/c5ra06019b

  日期：——

  X = Cl or Br; EWG₁, EWG₂ = electron withdrow group, one-pot reaction, 29 examples, yields from moderate to high, gram scale-up potential confirmed.

  X = 氯或溴；EWG1，EWG2 = 电子吸引基团，一锅法反应，29个例子，产率从中等到高，克级放大潜力得到确认。