| 1598436-27-1

• 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: 1598436-27-1
• 化学式: C₂₂H₁₈N₂O
• 分子量: 326.398
• InChiKey: POPWEFFLJLYLFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  32.67
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  、 3-苯基氨基-2-丙烯酸甲酯 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以0.543 g的产率得到methyl 1-benzyl-5-methyl-2-oxo-4′-(phenylamino)-3′,4′-dihydro-1′H-spiro[indoline-3,2′-quinoline]-3′-carboxylate
  参考文献：
  名称：

  Povarov Reaction of β-Enamino Esters and Isatin-3-imines for Diastereoselective Synthesis of Spiro[indoline-3,2′-quinolines]

  摘要：

  The p-toluenesulfonic acid catalyzed Povarov reaction of isatin-3-imines with beta-enamino esters, which were generated in situ from the reaction of arylamines and methyl propiolate in ethanol, afforded the polysubstituted spiro[indoline-3,2'-quinolines] in high yields and with high diastereoselectivity.

  DOI：

  10.1055/s-0033-1340459
• 作为产物：
  描述：

  5-甲基靛红 在 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Silver-catalyzed pyrazole migration and cycloaddition reaction of diazo pyrazoleamides with ketimines

  摘要：

  银催化的吡唑迁移和环化反应以高产率和非对映选择性的底物依赖方式得到了很好的证实。

  DOI：

  10.1039/d3cc03253a

文献信息

• Control of N-Heterocyclic Carbene Catalyzed Reactions of Enals: Asymmetric Synthesis of Oxindole-γ-Amino Acid Derivatives
  作者：Xiang-Yu Chen、Jia-Wen Xiong、Qiang Liu、Sun Li、He Sheng、Carolina von Essen、Kari Rissanen、Dieter Enders

  DOI：10.1002/anie.201708994

  日期：2018.1.2

  A strategy to control the switch between a non‐cycloaddition reaction and a cycloaddition reaction of enals, using N‐heterocyclic carbene (NHC) catalyisis, has been developed. The new scalable protocol leads to γ‐amino‐acid esters bearing a tetrasubstituted stereocenter in good yields and high stereoselectivities by homo‐Mannich reactions of enals and isatin‐derived ketimines. By simply changing the

  已经开发出一种利用N杂环卡宾（NHC）催化作用来控制烯类的非环加成反应和环加成反应之间的转换的策略。新的可扩展方案可通过Enals和伊斯汀衍生的酮亚胺的均相Mannich反应，以高收率和高立体选择性产生带有四取代立体中心的γ-氨基酸酯。通过简单地将N-酮亚胺取代基更改为邻-羟基苯基，即可获得相应的螺环氧代吲哚-γ-内酰胺。
• Highly diastereoselective synthesis of imidazolidine-dispirooxindoles via three-component [3 + 2] cycloadditions of isatins, 2-(aminomethyl)pyridine and isatin-based imines
  作者：Hong-Wu Zhao、Xiao-Qin Chen、Zhao Yang、Ting Tian、Bo Li、Wei Meng、Xiu-Qing Song、Hai-Liang Pang

  DOI：10.1039/c5ra21995g

  日期：——

  isatins, 2-(aminomethyl)pyridine and isatin-based imines proceeded readily, and furnished novel imidazolidine-dispirooxindoles in up to 84% yield with up to >99 : 1 diastereoselectivity. The relative configuration of the imidazolidine-dispirooxindoles was firmly confirmed on the basis of X-ray single crystal structure analysis. The reaction mechanism was assumed to account for the diastereoselective formation

  在存在Et 3 N的情况下，靛红，2-（氨基甲基）吡啶和基于靛红的亚胺的[3 + 2]环加成反应很容易进行，并以高达84％的产率提供了新颖的咪唑烷-二螺环辛多烯，其产率高达> 99： 1非对映选择性。基于X射线单晶结构分析，牢固地确认了咪唑烷-二螺并氧辛酯的相对构型。假定该反应机理解释了咪唑烷-二螺并恶唑的非对映选择性形成。
• Selective Synthesis of Functionalized Spiro[indoline-3,2′-pyridines] and Spiro[indoline-3,4′-pyridines] by Lewis Acid Catalyzed Reactions of Acetylenedicarboxylate, Arylamines, and Isatins
  作者：Hong Gao、Jing Sun、Chao-Guo Yan

  DOI：10.1021/jo500144z

  日期：2014.5.2

  The functionalized spiro[indoline-3,2'-pyridine]-3',4',5',6'-tetracarboxylates were efficiently synthesized by BF3 center dot OEt2-catalyzed reactions of isatin-3-imines with acetylenedicarboxylates in methylene dichloride. Under similar conditions, the BF3 center dot OEt2-catalyzed three-component reactions of acetylenedicarboxylates, arylamines, and isatins afforded functionalized spiro[indoline-3,4'-pyridine]-2',3',5',6'-tetracarboxylates in moderate yields.