ethyl 3-(4-chlorophenyl)indolizine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 3-(4-chlorophenyl)indolizine-1-carboxylate
• 英文别名: Ethyl 3-(4-chlorophenyl)indolizine-1-carboxylate
• 化学式: C₁₇H₁₄ClNO₂
• 分子量: 299.757
• InChiKey: VMTAGAJZRARBHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯乙炔 、 2-吡啶乙酸乙酯 在 过氧化氢异丙苯 、 碘 、 sodium acetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以94%的产率得到ethyl 3-(4-chlorophenyl)indolizine-1-carboxylate
  参考文献：
  名称：

  Tuning radical reactivity using iodine in oxidative C(sp³)–H/C(sp)–H cross-coupling: an easy way toward the synthesis of furans and indolizines

  摘要：

  分子碘被发现是一种有效的氧化还原催化剂，可用于羰基化合物与末端炔烃的氧化交叉偶联反应。

  DOI：

  10.1039/c5cc01825k

文献信息

• Metal-free synthesis of indolizines through oxidative C C and C N bond formations of C (sp 3 ) H bonds
  作者：N. Naresh Kumar Reddy、Darapaneni Chandra Mohan、Subbarayappa Adimurthy

  DOI：10.1016/j.tetlet.2016.01.082

  日期：2016.3

  catalyzed synthesis of indolizine-1-carboxylates through oxidative CC and CN bond formations by the reaction of 2-pyridyl acetates with alkynes and alkenes without metal, oxidant, and base. This procedure is compatible with a broad range of functional groups in both alkynes and alkenes with good yields. The reaction proceeds through a tandem CC bond formation followed by an intramolecular cyclization

  碘催化乙酸2-吡啶酯与炔烃和没有金属，氧化剂和碱的烯烃的反应，通过氧化C C和C N键的形成，催化碘吲哚-1-羧酸酯的合成。该方法与炔烃和烯烃中的多种官能团相容，且收率良好。该反应通过串联C C键的形成进行，随后进行分子内环化。
• Tuning radical reactivity using iodine in oxidative C(sp³)–H/C(sp)–H cross-coupling: an easy way toward the synthesis of furans and indolizines
  作者：Shan Tang、Kun Liu、Yue Long、Xiaotian Qi、Yu Lan、Aiwen Lei

  DOI：10.1039/c5cc01825k

  日期：——

  Molecular iodine was found to be an effective redox catalyst for the oxidative cross-coupling of carbonyl compounds with terminal alkynes.

  分子碘被发现是一种有效的氧化还原催化剂，可用于羰基化合物与末端炔烃的氧化交叉偶联反应。
• Indolizine Synthesis via Oxidative Cross-Coupling/Cyclization of Alkenes and 2-(Pyridin-2-yl)acetate Derivatives
  作者：Ren-Rong Liu、Jian-Jun Hong、Chuan-Jun Lu、Meng Xu、Jian-Rong Gao、Yi-Xia Jia

  DOI：10.1021/acs.orglett.5b01334

  日期：2015.6.19

  A novel copper/I2-mediated oxidative cross-coupling/cyclization of 2-(pyridin-2-yl)acetate derivatives and simple olefins is developed, which provides a straightforward and efficient access to structural diversely indolizines. A series of 1,3-di- and 1,2,3-trisubstituted indolizines are easily synthesized in modest to excellent yields.

  开发了新颖的铜/ I 2介导的2-（吡啶-2-基）乙酸酯衍生物和简单烯烃的氧化交叉偶联/环化，其提供了直接且有效地获得结构多样的吲哚嗪的途径。一系列1,3-二-和1,2,3-三取代的吲哚嗪很容易合成，收率适中至优异。
• An I₂-catalyzed oxidative cyclization for the synthesis of indolizines from aromatic/aliphatic olefins and α-picoline derivatives
  作者：Likui Xiang、Fuming Zhang、Baohua Chen、Xiaobo Pang、Xiaodong Yang、Guosheng Huang、Rulong Yan

  DOI：10.1039/c5ra01234a

  日期：——

  A novel I2-catalyzed intermolecular oxidative tandem cyclization reaction of aromatic/aliphatic olefins and α-picoline derivatives has been achieved for the synthesis of indolizines under metal-free conditions. In this transformation, substituted indolizines are obtained in moderate to good yields through C–C/C–N bond formation in one pot.

  已经实现了新颖的I 2催化的芳香族/脂肪族烯烃和α-甲基吡啶衍生物的分子间氧化串联环化反应，用于在无金属条件下合成吲哚类。在这一转化过程中，通过在一个罐中形成C–C / C–N键，可以以中等到良好的产率获得取代的吲哚嗪。
• 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。