3-formyl-indolizine-1-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 3-formyl-indolizine-1-carboxylic acid ethyl ester
• 英文别名: ethyl 3-formylindolizine-1-carboxylate
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: RYJCVLADXKFHGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-pyridin-2-yl-pent-4-ynoic acid ethyl ester 在 碘 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 以83%的产率得到3-formyl-indolizine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  A novel approach to 3-acylated indolizine structures via iodine-mediated hydrative cyclization

  摘要：

  We have discovered a new route to 3-acylated indolizine structures via iodine-mediated hydrative cyclization. Reaction mechanism is proposed for this novel transformation, which involves a 5-exo-dig iodocyclization, deprotonation, incorporation of another iodo group, deprotonation, and subsequent replacement of the diiodo group by H2O. Various 3-acylated indolizine derivatives were obtained using this mild procedure in good yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.101

文献信息

• Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines
  作者：Zhengwang Chen、Pei Liang、Xiaoyue Ma、Haiqing Luo、Guohai Xu、Tanggao Liu、Xiaowei Wen、Jing Zheng、Hui Ye

  DOI：10.1021/acs.joc.8b02883

  日期：2019.2.1

  A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.
• A novel approach to 3-acylated indolizine structures via iodine-mediated hydrative cyclization
  作者：Ikyon Kim、Sun Gi Kim、Ji Young Kim、Ge Hyeong Lee

  DOI：10.1016/j.tetlet.2007.10.101

  日期：2007.12

  We have discovered a new route to 3-acylated indolizine structures via iodine-mediated hydrative cyclization. Reaction mechanism is proposed for this novel transformation, which involves a 5-exo-dig iodocyclization, deprotonation, incorporation of another iodo group, deprotonation, and subsequent replacement of the diiodo group by H2O. Various 3-acylated indolizine derivatives were obtained using this mild procedure in good yields. (c) 2007 Elsevier Ltd. All rights reserved.