ethyl 2-(2-oxoindolin-3-ylidene)cyanoacetate

• 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: ethyl 2-(2-oxoindolin-3-ylidene)cyanoacetate
• 英文别名: ethyl 2-cyano-2-(2-oxoindolin-3-ylidene)acetate；(Z)-Ethyl 2-cyano-2-(2-oxoindolin-3-ylidene)acetate；ethyl 2-cyano-2-(2-oxo-1H-indol-3-ylidene)acetate
• 化学式: C₁₃H₁₀N₂O₃
• mdl: MFCD00187827
• 分子量: 242.234
• InChiKey: USFZCQWVLYCKDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-oxoindolin-3-ylidene)cyanoacetate 在 二氢吡啶 作用下， 以 乙醇 、 苯 为溶剂， 反应 1.0h， 以87%的产率得到ethyl 2-cyano-2-(2-oxo-2,3-dihydro-1H-3-indolyl)acetate
  参考文献：
  名称：

  Synthetic and Theoretical Studies on the Reduction of Electron Withdrawing Group Conjugated Olefins Using the Hantzsch 1,4-Dihydropyridine Ester

  摘要：

  The Hantzsch 1,4-dihydropyridine ester (1) has been observed to be a useful selective reducing agent for the reduction of electron-withdrawing conjugated double bonds. The rate of this reaction was observed to be dependent upon the nature of the conjugated substituents and, consequently, the electronic nature of the unsaturated double bond. Theoretical calculations confirmed the importance of the HOMO-LUMO gap for this reaction and implicated a hydride transfer, agreeing with the experimentally observed reaction rate order. The calculations also revealed the importance of a boatlike structure of the 1,4-dihydropyridine nucleus as well as a trans arrangement of the ester groups to facilitate the hydride transfer.

  DOI：

  10.1021/jo034921e
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 乙醇 作用下， 生成 ethyl 2-(2-oxoindolin-3-ylidene)cyanoacetate
  参考文献：
  名称：

  Pietra, Farmaco, Edizione Scientifica, 1957, vol. 12, p. 946,951

  摘要：

  DOI：

文献信息

• Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast
  作者：Arianna Rossetti、Alessandro Sacchetti、Marta Bonfanti、Gabriella Roda、Giulia Rainoldi、Alessandra Silvani

  DOI：10.1016/j.tet.2017.06.022

  日期：2017.8

  materials toward more complex oxindole-based structures. These molecules can be prepared by the reduction of a 3-ylidene oxindole precursor by classical metal-catalysed chemical reductions of the olefin. In this work we present a biocatalytic approach for the reduction of oxindole-based olefins using baker's yeast. All the substrates were efficiently reduced in high yields. When an α,β-unsaturated ketone

  3-取代的羟吲哚由于其潜在的生物活性和作为朝向更复杂的以羟吲哚为基础的结构的起始材料的作用而成为非常有趣的分子。这些分子可以通过烯烃的经典金属催化化学还原反应，通过还原3-亚甲基羟吲哚前体来制备。在这项工作中，我们提出了一种利用面包酵母还原基于氧吲哚的烯烃的生物催化方法。有效地减少了所有基板的高产量。当使用α，β-不饱和酮时，以高收率和ee获得相应的饱和醇。为了进一步研究酶-底物的相互作用，还进行了分子对接研究。
• Three-Component Synthesis of Spiro[Indoline-3,4'-Pyrano[3,2-b]Pyran]- 2,8'-Diones Using a One-Pot Reaction
  作者：Abbas Rahmati、Zahra Khalesi、Tahmineh Kenarkoohi

  DOI：10.2174/13862073113166660067

  日期：2014.1.31

  A one-pot, three-component reaction of an isatin and kojic acid with an active methylene compound such as ethyl cyanoacetate, methyl cyanoacetate and malononitrile in methanol using catalytic amount of DABCO to give 2'- amino-6'-(hydroxymethyl)-8'H-spiro[indoline-3,4'-pyrano[3,2-b]pyran]-2,8'-diones in good to excellent yields under reflux conditions, is described.

  本文描述了一种一锅法的三组分反应，其中使用了异靛酮和曲酸与活性亚甲基化合物（如氰基乙酸乙酯、氰基乙酸甲酯和马隆腈）在甲醇中反应，使用催化量的DABCO，在回流条件下有效地生成2'-氨基-6'-(羟甲基)-8'H-螺旋[吲哚-3,4'-吡喃[3,2-b]吡喃]-2,8'-二酮，产率良好到优异。
• Synthesis of Novel Spiro Cyclic 2-Oxindole Derivatives of 6-Amino-4H-Pyridazine via [3+3] Atom Combination Utilizing Chitosan as a Catalyst
  作者：Ismail Abdelhamid

  DOI：10.1055/s-0028-1087558

  日期：2009.3

  Azaenamines were reacted with 3-cyanomethylidene-2-oxindoles using chitosan catalyst to yield spirocyclic 2-oxindole derivatives of 6-amino-4H-pyridazine and fused pyridazinoquinazolines.

  阿扎氨基化合物与3-氰甲基亚胺-2-氧吲哚在壳聚糖催化剂的作用下反应，生成了6-氨基-4H-吡嗪衍生物和融合的吡嗪喹唑啉的螺环2-氧吲哚衍生物。
• DBU-Catalyzed, facile and efficient method for synthesis of spirocyclic 2-oxindole derivatives with incorporated 6-amino-4H-pyridazines and fused derivatives via [3+3] atom combination
  作者：Ismail A. Abdelhamid、Mona H. Mohamed、Amr M. Abdelmoniem、Said A.S. Ghozlan

  DOI：10.1016/j.tet.2009.09.081

  日期：2009.11

  3-Cyanomethylidene oxindole derivatives were prepared in excellent yields utilizing DBU-promoted Knoevenagel condensation of isatin derivatives with active methylene reagents. The isolated products were then reacted with azaenamines via a DBU-promoted Michael addition to yield spirocyclic 2-oxindole derivatives with incorporated 6-amino-4H-pyridazines and their fused derivatives.

  利用DBU促进的Isatin衍生物的Knoevenagel缩合反应与活性亚甲基试剂以极好的收率制备了3-Cyanomethylidene oxindole衍生物。然后将分离的产物通过DBU-促进的迈克尔加成与氮杂烯胺反应，得到螺环2-氧吲哚衍生物，其中引入了6-氨基-4 H-哒嗪及其稠合衍生物。
• SYNTHESIS OF NEW FUSED AND SPIRO HETEROCYCLES DERIVED FROM 4-AMINO-5-MERCAPTO-3-TRIFLUOROMETHYL-1,2,4-TRIAZOLE
  作者：A. M. El-sayed、A. Khodairy

  DOI：10.1080/10426509808036972

  日期：1998.1.1

  Abstract Some new heterocyclic systems 2-9 were obtained through the reaction of 4-amino-5-mercapto-3-trifluoromethyl-1,2,4-triazole (1) with ylidenemalononitriles, 1,3-diketones, halonitriles, active nitriles, aromatic aldehydes or ketones. Also spiro systems 10-12 were achieved in one pot synthesis by addition of compound 1 to isatine, cycloalkanones or ylidenenitriles followed by cyclization. The

  摘要 4-氨基-5-巯基-3-三氟甲基-1,2,4-三唑(1)与亚基丙二腈、1,3-二酮、卤腈、活性腈、芳香醛或酮。螺环系统10-12也通过将化合物1加成到靛红、环烷酮或亚芳基腈然后环化而在一锅合成中获得。化合物1与3[二(甲硫基)-亚甲基]戊-2,4-二酮反应得到化合物13，用环烷酮处理得到化合物14。