ethyl 3-(thiophen-2-yl)indolizine-1-carboxylate

• 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: ethyl 3-(thiophen-2-yl)indolizine-1-carboxylate
• 英文别名: Ethyl 3-thiophen-2-ylindolizine-1-carboxylate；ethyl 3-thiophen-2-ylindolizine-1-carboxylate
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: AFQSWNLNBDTLPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙烯基噻吩 、 2-吡啶乙酸乙酯 在 copper diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以85%的产率得到ethyl 3-(thiophen-2-yl)indolizine-1-carboxylate
  参考文献：
  名称：

  Copper-Catalyzed Oxidative Coupling–Annulation: One-Pot Synthesis of Indolizines from 2-Alkylazaarenes with Alkenes

  摘要：

  A novel copper-catalyzed highly selective oxidative coupling-annulation of 2-alkylazaarenes with terminal alkenes was achieved. This process provides a simple, efficient, and atom-economic way to construct indolizines in good yields.

  DOI：

  10.1055/s-0034-1378785

文献信息

• Iodine-Mediated Oxidative Cyclization of 2-(Pyridin-2-yl)acetate Derivatives with Alkynes: Condition-Controlled Selective Synthesis of Multisubstituted Indolizines
  作者：Lisheng He、Yuzhu Yang、Xiaolan Liu、Guangyan Liang、Chunyan Li、Daoping Wang、Weidong Pan

  DOI：10.1055/s-0039-1690229

  日期：2020.2

  An iodine-mediated oxidative cyclization reaction between 2-(pyridin-2-yl)acetate derivatives and different alkynes has been developed, which provides regioselective and chemoselective syntheses of multiply substituted indolizines under modified reaction conditions. Plausible mechanisms have been proposed to explain the selective syntheses of indolizines. This protocol can be also applied to the stepwise

  已经开发出碘介导的2-（吡啶-2-基）乙酸酯衍生物与不同炔烃之间的碘介导的氧化环化反应，该反应在修饰的反应条件下提供了多重取代的吲哚嗪的区域选择性和化学选择性合成。已经提出了合理的机制来解释吲哚嗪的选择性合成。该方案也可以应用于2,2'-联吲哚并逐步合成。
• Synthesis of substituted indolizines via radical oxidative decarboxylative annulation of 2-(pyridin-2-yl)acetate derivatives with α,β-unsaturated carboxylic acids
  作者：Jian Gu、Chun Cai

  DOI：10.1039/c6ob01902a

  日期：——

  A copper mediated radical oxidative annulation of 2-(pyridin-2-yl)acetate derivatives with α,β-unsaturated carboxylic acids is developed. This study offers a new and expedient strategy for the synthesis of useful indolizines in moderate to good yields and exhibits a broad substrate scope and good functional group tolerance.

  开发了铜介导的2-（吡啶-2-基）乙酸酯衍生物与α，β-不饱和羧酸的自由基氧化环化反应。这项研究为中度到良好的产率合成有用的吲哚嗪提供了一种新的权宜之计，并且具有广泛的底物范围和良好的官能团耐受性。
• Copper-Catalyzed Oxidative Coupling–Annulation: One-Pot Synthesis of Indolizines from 2-Alkylazaarenes with Alkenes
  作者：Ying Liang、Ying-ming Pan、Jing-ling Liu、Heng-shan Wang

  DOI：10.1055/s-0034-1378785

  日期：——

  A novel copper-catalyzed highly selective oxidative coupling-annulation of 2-alkylazaarenes with terminal alkenes was achieved. This process provides a simple, efficient, and atom-economic way to construct indolizines in good yields.