(1'R,8a'R)-3'-amino-5-bromo-2-oxo-6',7'-dihydro-2'H-spiro[indoline-3,1'-naphthalene]-2',2',4'(8'H,8a'H)-tricarbonitrile

• 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
• 英文名称: (1'R,8a'R)-3'-amino-5-bromo-2-oxo-6',7'-dihydro-2'H-spiro[indoline-3,1'-naphthalene]-2',2',4'(8'H,8a'H)-tricarbonitrile
• 英文别名: (3R,4'aR)-2'-amino-5-bromo-2-oxospiro[1H-indole-3,4'-4a,5,6,7-tetrahydronaphthalene]-1',3',3'-tricarbonitrile
• 化学式: C₂₀H₁₄BrN₅O
• 分子量: 420.268
• InChiKey: HXTPRPHSPNDIKK-VLIAUNLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-溴靛红 、 环己酮 、 丙二腈 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以63%的产率得到(1'R,8a'R)-3'-amino-5-bromo-2-oxo-6',7'-dihydro-2'H-spiro[indoline-3,1'-naphthalene]-2',2',4'(8'H,8a'H)-tricarbonitrile
  参考文献：
  名称：

  螺吲哚-3,1'-萘四环体系的一般方法：靛红和环状酮与两分子丙二腈的立体选择性拟四组分反应†

  摘要：

  发现了一种新型的催化立体选择性级联伪四组分反应。在环境温度下，三乙胺催化的靛红，环酮与两个分子的丙二腈的简单，容易的假四组分反应，立体选择性地形成了60-90％产率的四环螺并氧杂吲哚。因此，直接从合理的起始化合物中发现了一种新的简单有效的“一锅法”，用于合成取代的螺氧并吲哚。在该假四组分反应中，在两个或三个中心获得了独特的立体选择性。

  DOI：

  10.1039/c5ra03452c

文献信息

• General approach to a spiro indole-3,1′-naphthalene tetracyclic system: stereoselective pseudo four-component reaction of isatins and cyclic ketones with two molecules of malononitrile
  作者：M. N. Elinson、A. N. Vereshchagin、R. F. Nasybullin、S. I. Bobrovsky、A. I. Ilovaisky、V. M. Merkulova、I. S. Bushmarinov、M. P. Egorov

  DOI：10.1039/c5ra03452c

  日期：——

  with two molecules of malononitrile catalyzed by triethylamine at ambient temperature stereoselectively results in the formation of tetracyclic spirooxindoles in 60–90% yields. Thus, a new simple and efficient ‘one-pot’ method to synthesize substituted spirooxindoles was found directly from reasonable starting compounds. Unique stereoselectivety was achieved on two or three centers in this pseudo four-component

  发现了一种新型的催化立体选择性级联伪四组分反应。在环境温度下，三乙胺催化的靛红，环酮与两个分子的丙二腈的简单，容易的假四组分反应，立体选择性地形成了60-90％产率的四环螺并氧杂吲哚。因此，直接从合理的起始化合物中发现了一种新的简单有效的“一锅法”，用于合成取代的螺氧并吲哚。在该假四组分反应中，在两个或三个中心获得了独特的立体选择性。
• Enantioselective assembly of functionalized carbocyclic spirooxindoles using an<scp>l</scp>-proline derived thiourea organocatalyst
  作者：V. Pratap Reddy Gajulapalli、Poopathy Vinayagam、Venkitasamy Kesavan

  DOI：10.1039/c4ra13711f

  日期：——

  Enantioselective sequential vinylogous Michael addition–cyclization reactions of vinyl malononitriles with isatylidene malononitrile were accomplished usingl-proline derived bifunctional thiourea.

  使用l-脯氨酸衍生的双官能硫脲，成功实现了对乙烯基丙二腈与异喹啉丙二腈进行对映选择性顺序烯丙基迈克尔加成-环化反应。
• A bifunctional Yolk–Shell nanocatalyst with Lewis and organic functional base for the synthesis of spirooxindoles
  作者：Somaye Mohammadi、Hossein Naeimi

  DOI：10.1016/j.apcata.2020.117720

  日期：2020.7

  Guanidine supported on magnetic YSNPs MgFe2O4 nanoparticles was created and estimated as a recoverable nanocatalyst for the synthesis of spirooxindole compounds in excellent yields. This nanocatalyst has two active base sites one of which them is Lewis base on the core such as nanoreactor and the other is organic base on the shell. This novel nanocatalyst was prepared and characterized by using FT-IR spectra, X-ray diffraction (XRD), TPD analysis, X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), thermo gravimetric analysis (TGA), Brunauer-Emmett-Teller (BET) and vibrating sample magnetometer (VSM). The catalyst can be recovered and recycled 6 times without marked loss of activity.