2-呋喃-2-吲哚嗪 | 28795-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 2-呋喃-2-吲哚嗪
• 英文名称: 2-(furan-2-yl)indolizine
• 英文别名: 2-(2-furyl)indolizine
• CAS: 28795-34-8
• 化学式: C₁₂H₉NO
• mdl: MFCD08277604
• 分子量: 183.21
• InChiKey: UGGLREXOFWHWIW-UHFFFAOYSA-N

物化性质

• 熔点：
  137 °C(Solv: ethanol (64-17-5))
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.6
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-呋喃-2-吲哚嗪 在 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 生成 3-Nitroso-2-(fur-2-yl)-indolizin
  参考文献：
  名称：

  3-Nitroso derivatives of 2-(furyl-2)-indolizine, 2-(furyl-2)-imidazo[1,2-a]pyridine, and its substitution products

  摘要：

  DOI：

  10.1007/bf00771315
• 作为产物：
  描述：

  1-(2-furan-2-yl-2-oxo-ethyl)-2-methyl-pyridinium; bromide 在 碳酸氢钠 作用下， 以 水 为溶剂， 生成 2-呋喃-2-吲哚嗪
  参考文献：
  名称：

  Synthesis and antimicrobic effect of furyl-substituted indolizine, imidazo[1,2-a]pyridine, and imidazo[2,1-b]thiazole

  摘要：

  DOI：

  10.1007/bf00771802

文献信息

• Regioselective C–H dithiocarbamation of indolizines with tetraalkylthiuram disulfide under metal-free conditions
  作者：Xiang Liu、Dan Song、Zemin Zhang、Jiatong Lin、Canzhan Zhuang、Haiying Zhan、Hua Cao

  DOI：10.1039/d1ob00701g

  日期：——

  disulfide has been described. A series of indolizine-dithiocarbamate derivatives were easily accessed in moderate to good yields with a broad scope. In addition, imidazo[1,2-a]pyridines were also well tolerated to afford diverse imidazoheterocycle-dithiocarbamate products, which are expected to be utilized for drug discovery. Of note, the reaction could be readily scaled up, and shows its practical value in

  已经描述了用四烷基秋兰姆二硫化物对中氮茚进行有效且直接的无金属区域选择性 C-H 二硫代氨基甲酸化。一系列中氮茚-二硫代氨基甲酸酯衍生物很容易以中等至良好的收率获得，范围广泛。此外，咪唑并[1,2 - a ]吡啶也具有良好的耐受性，可提供多种咪唑杂环-二硫代氨基甲酸酯产品，有望用于药物发现。值得注意的是，该反应可以很容易地放大，并显示出其在有机合成中的实用价值。
• Mechanochemical Synthesis of 1,2-Diketoindolizine Derivatives from Indolizines and Epoxides Using Piezoelectric Materials
  作者：Yumei Wang、Ziwu Zhang、Lichan Deng、Tianfeng Lao、Zhengquan Su、Yue Yu、Hua Cao

  DOI：10.1021/acs.orglett.1c02575

  日期：2021.9.17

  A simple and efficient mechanochemical-induced approach for the synthesis of 1,2-diketoindolizine derivatives has been developed. BaTiO3 was used as the piezoelectric material in this transformation. This method features no usage of solvent, simple experimental operation, scalable potential, and high conversion efficiency, which make it attractive and practical.

  已经开发了一种简单有效的机械化学诱导方法来合成 1,2-二酮吲哚嗪衍生物。BaTiO 3用作该转变中的压电材料。该方法不使用溶剂，实验操作简单，潜力可扩展，转化效率高，具有吸引力和实用性。
• Synthesis of Pyrrolo[2,1,5-<i>cd</i>]indolizine Rings via Visible-Light-Induced Intermolecular [3+2] Cycloaddition of Indolizines and Alkynes
  作者：Yu Zhang、Yue Yu、Bing-bing Liang、Yong-yan Pei、Xiang Liu、Hua-gang Yao、Hua Cao

  DOI：10.1021/acs.joc.0c01253

  日期：2020.8.21

  smoothly underwent visible-light-induced intermolecular [3+2] annulations with internal alkynes to afford pyrrolo[2,1,5-cd]indolizine in good to excellent yields with high regioselectivity. Through this cascade reaction, a series of fluoroactive fused indolizines with a large π-system were conveniently synthesized. The usage of visible light as energy source with air as a stoichiometric oxidant under

  一系列吲哚并嗪通过内部炔烃顺利地进行了可见光诱导的分子间[3 + 2]环空拆分，从而以良好的产率和良好的区域选择性提供了吡咯并[2,1,5- cd ]吲哚并嗪。通过该级联反应，方便地合成了具有大π系统的一系列含氟稠合吲哚嗪。在简单条件下使用可见光作为能源，以空气作为化学计量的氧化剂，使该过程具有吸引力和实用性。
• Visible-Light-Induced Regioselective Dicarbonylation of Indolizines with Oxoaldehydes via Direct C–H Functionalization
  作者：Lili Teng、Xiang Liu、Pengfeng Guo、Yue Yu、Hua Cao

  DOI：10.1021/acs.orglett.0c01094

  日期：2020.5.15

  A metal-free system for regioselective dehydrogenative cross-couplings between indolizines and oxoaldehydes catalyzed by visible light under mild conditions has been described. As an atom economical and eco-friendly protocol, the reaction proceeds in good yields using inexpensive, readily available visible-light sources and the environmentally friendly oxidant oxygen. Various valuable 1,2-dicarbonyl

  已经描述了在温和条件下可见光催化的吲哚嗪和氧醛之间的区域选择性脱氢交叉偶联的无金属体系。作为一种原子经济且环保的方案，使用廉价，易于获得的可见光源和环境友好的氧化剂氧气，可以高产率进行反应。通过sp2 CH键的直接二羰基化，可以轻松获得与吲哚嗪核心相连的各种有价值的1,2-二羰基衍生物。
• Mechanochemically Induced Dehydrogenation Coupling and [3+2] Cycloaddition of Indolizines with Allenes Using Piezoelectric Materials
  作者：Mingzhou Huang、Lichan Deng、Tianfeng Lao、Ziwu Zhang、Zhengquan Su、Yue Yu、Hua Cao

  DOI：10.1021/acs.joc.1c02940

  日期：2022.3.4

  wide range of indolizines with allenes proceeded smoothly under mechanochemically induced conditions via a [3+2] annulation process, affording various substituted pyrrolo[2,1,5-cd]indolizines in good yields. The reaction efficiency was greatly improved by using piezoelectric material as the charge transfer catalyst. The photophysical properties of the resulting pyrrolo[2,1,5-cd]indolizine were characterized

  在机械化学诱导的条件下，通过 [3+2] 环化过程，各种含烯的吲哚嗪顺利进行，以良好的收率得到各种取代的吡咯并[2,1,5-cd]吲哚嗪。使用压电材料作为电荷转移催化剂，反应效率大大提高。表征了所得吡咯并[2,1,5-cd]吲哚嗪的光物理性质。