| 1415985-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• CAS: 1415985-05-5
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: NQWSRTDPJZOIIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以65%的产率得到(3Z)-3-(3-chlorobut-3-en-2-ylidene)-7-methoxy-1H-indol-2-one
  参考文献：
  名称：

  Direct FeX₃-Based Stereocontrolled Access to (Z)-3-Alkenyl-oxindoles from Allenols

  摘要：

  Iron trihalides (FeCl3 and FeBr3) smoothly promote the halogenation/rearrangement of 2-indolinone-tethered allenols to efficiently afford 3-halodienyl-oxindoles with good yield and total selectivity. Also, 2-halo-1,3-dienes are synthetically interesting building blocks for the preparation of functionalized 3-alkenyl-oxindoles through a Suzuki-Miyaura reaction.

  DOI：

  10.1021/jo302296r
• 作为产物：
  描述：

  7-甲氧基靛红 、 1-溴-2-丁炔 在 indium 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 以76%的产率得到
  参考文献：
  名称：

  Direct FeX₃-Based Stereocontrolled Access to (Z)-3-Alkenyl-oxindoles from Allenols

  摘要：

  Iron trihalides (FeCl3 and FeBr3) smoothly promote the halogenation/rearrangement of 2-indolinone-tethered allenols to efficiently afford 3-halodienyl-oxindoles with good yield and total selectivity. Also, 2-halo-1,3-dienes are synthetically interesting building blocks for the preparation of functionalized 3-alkenyl-oxindoles through a Suzuki-Miyaura reaction.

  DOI：

  10.1021/jo302296r

文献信息

• Gold-Photoredox-Cocatalyzed Tandem Oxycyclization/Coupling Sequence of Allenols and Diazonium Salts with Visible Light Mediation
  作者：Benito Alcaide、Pedro Almendros、Borja Aparicio、Carlos Lázaro-Milla、Amparo Luna、Olalla Nieto Faza

  DOI：10.1002/adsc.201700598

  日期：2017.8.17

  The room temperature radical cycloetherification/arylation cascade of allenols and diazonium salts has been accomplished via a combination of gold and photoredox catalysis to provide 2,3,4‐trisubstituted‐2,5‐dihydrofurans. The functionalized oxacycle formation sequence is chemo‐ and regioselective for the cycloetherification and for the position that bears the aryl moiety after the cross‐coupling.

  烯醇和重氮盐的室温自由基环醚化/芳基化级联反应已通过金和光氧化还原催化的组合完成，从而提供了2,3,4-三取代-2,5-二氢呋喃。功能化的氧杂环形成序列对环醚化以及交叉偶联后带有芳基部分的位置具有化学和区域选择性。机理研究表明，这种转变是通过金（I）初始氧化为苯基金（III）配合物而进行的，该配合物与烯丙基配位后，催化其环化并在还原消除后生成偶联产物，从而生成金（I） ）。
• Gallium-Catalyzed Domino Arylation/Oxycyclization of Allenes with Phenols
  作者：Benito Alcaide、Pedro Almendros、Fernando Herrera、Amparo Luna、M. Elena de Orbe、M. Rosario Torres

  DOI：10.1021/acs.joc.5b00106

  日期：2015.4.17

  The synthesis of dihydrobenzofuran-appended oxindoles has been accomplished taking advantage of an unprecedented reaction between allenols and phenols under metal catalysis.
• Direct FeX₃-Based Stereocontrolled Access to (<i>Z</i>)-3-Alkenyl-oxindoles from Allenols
  作者：Benito Alcaide、Pedro Almendros、Amparo Luna、Natividad Prieto

  DOI：10.1021/jo302296r

  日期：2012.12.21

  Iron trihalides (FeCl3 and FeBr3) smoothly promote the halogenation/rearrangement of 2-indolinone-tethered allenols to efficiently afford 3-halodienyl-oxindoles with good yield and total selectivity. Also, 2-halo-1,3-dienes are synthetically interesting building blocks for the preparation of functionalized 3-alkenyl-oxindoles through a Suzuki-Miyaura reaction.