(1'R,8a'R)-3'-amino-2-oxo-6',7'-dihydro-2'H-spiro[indoline-3,1'-naphthalene]-2',2',4'(8'H,8a'H)-tricarbonitrile | 1613459-54-3

• 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-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-2-oxospiro[1H-indole-3,4'-4a,5,6,7-tetrahydronaphthalene]-1',3',3'-tricarbonitrile
• CAS: 1613459-54-3
• 化学式: C₂₀H₁₅N₅O
• 分子量: 341.372
• InChiKey: OFZHUKWHABAHGS-VLIAUNLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 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：

  2-环己基亚己基丙二腈 、 靛红 、 丙二腈 在 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((S)-1-methylpyrrolidin-2-yl)(phenyl)methyl)thiourea 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以88%的产率得到(1'R,8a'R)-3'-amino-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：

  Enantioselective assembly of functionalized carbocyclic spirooxindoles using anl-proline derived thiourea organocatalyst

  摘要：

  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。

  DOI：

  10.1039/c4ra13711f

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。
• Organocatalytic enantioselective construction of multi-functionalized spiro oxindole dienes
  作者：Xiao-Fei Huang、Ya-Fei Zhang、Zheng-Hang Qi、Nai-Kai Li、Zhi-Cong Geng、Kun Li、Xing-Wang Wang

  DOI：10.1039/c4ob00545g

  日期：——

  A diastereo- and enantio-selective domino Michael-cyclization–tautomerization reaction of isatylidene malononitriles with α,α-dicyanoalkenes catalyzed by a cinchona alkaloid-derived bifunctional thiourea catalyst has been developed. A series of multi-functionalized spiro oxindole diene derivatives have been obtained in good to excellent yields (up to 97%) with good to excellent enantioselectivities (up to 96%) as well as good diastereoselectivities (up to 7.9 : 1). In addition, an anomalous temperature effect on the enantioselectivity has also been studied for this transformation.

  已开发出一种异构体和对应选择性多米诺迈克尔环化-异亚丙基丙二腈与α,α-二氰基烯烃的环化-互变异构选择性反应，该反应由金鸡纳生物碱衍生的双功能硫脲催化剂催化。已获得一系列多功能化的螺环吲哚二烯衍生物，其产率良好至极佳（高达97%），对应选择性良好至极佳（高达96%），以及立体选择性良好（高达7.9：1）。此外，还研究了这种转化中温度对对应选择性的异常影响。
• 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.
• 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。