ethyl cyano(5-methyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetate | 897585-04-5

• 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
• 英文名称: ethyl cyano(5-methyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetate
• 英文别名: ethyl 2-cyano-2-(5-methyl-2-oxo-1H-indol-3-ylidene)acetate
• CAS: 897585-04-5
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: MQDCHZBALFCDBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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 cyano(5-methyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetate 在 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 ethyl 3-acetyl-9-benzyl-4-cyano-6-methyl-4,9-dihydropyrano[2,3-b]indole-4-carboxylate
  参考文献：
  名称：

  Phosphorus-containing Lewis base catalyzed highly regioselective cyclization of isatin derived electron-deficient alkenes with but-3-yn-2-one

  摘要：

  In this paper, we reported that phosphorus-containing Lewis bases catalyzed [4+2] cyclization of N-protected isatin derived electron-deficient alkenes with but-3-yn-2-one could proceed smoothly to give the corresponding dihydropyrano[2,3-b]indoles in good to excellent yields under mild conditions. The substrate scope has been carefully examined and the plausible reaction mechanism has been also proposed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.036
• 作为产物：
  描述：

  5-甲基靛红 、 氰乙酸乙酯 以 乙醇 、 水 为溶剂， 生成 ethyl cyano(5-methyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetate
  参考文献：
  名称：

  碱控制雕白粉介导的异亚烷基丙二腈/氰乙酸酯的还原羟醛/环化和二聚化

  摘要：

  在这项研究中，我们开发了一种新颖的方法，涉及碱控制、雕白粉介导的还原/羟醛反应，然后进行亚莠亚基丙二腈/氰乙酸酯的环化，从而合成螺[2,3-二氢呋喃-3,3'-羟吲哚]。此外，我们还公开了雕白粉介导的亚茚亚基丙二腈的二聚方法，产生二螺[环戊-3'-烯]二异吲哚。在该反应中使用雕白粉具有双重目的，既充当还原剂又充当 C1 合成子。该方法具有反应装置简单、底物范围广、所需时间短、使用水作为绿色溶剂、不需要金属或催化剂、产物可以通过过滤轻松分离、在温和反应条件下收率优异等优点。

  DOI：

  10.1039/d3ob01794j

文献信息

• Synthesis of 2,6′-Dioxo-1′,5′,6′,7′-tetrahydrospiro[indoline-3,4′-pyrazolo[3,4-<i>b</i>]pyridine]-5′-carbonitriles via a One-Pot, Three-Component Reaction in Water
  作者：Abbas Rahmati、Tahmineh Kenarkoohi、Hamid Reza Khavasi

  DOI：10.1021/co300047j

  日期：2012.12.10

  A one-pot, three-component condensation reaction of an isatin, aminopyrazole, and alkyl cyanoacetate in water to give 2,6′-dioxo-1′,5′,6′,7′-tetrahydrospiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-5′-carbonitrile with good yields, at 90 °C, using a Et3N as catalyst, is described.

  靛红，氨基吡唑和氰基乙酸烷基酯在水中的一锅三组分缩合反应，得到2,6'-dioxo-1'，5'，6'，7'-四氢螺[吲哚啉-3,4'描述了在90℃下使用Et 3 N作为催化剂具有良好收率的-吡唑并[3，4- b ]吡啶] -5′-腈。
• Synthesis of new heterocyclic systems—substituted spiro[chromene-4,3′-indoles] and spiro[indole-3,4′-quinolines]
  作者：S. A. Pogosyan、Dzh. A. Avakimyan、H. M. Stepanyan

  DOI：10.1134/s1070428016090098

  日期：2016.9

  Methods have been developed for the synthesis of new heterocyclic systems, spiro[chromene-4,3′- indoles] and spiro[indole-3,4′-quinolines] by the base-catalyzed domino reaction of isatins with 5,5-dimethylcyclohexane- 1,3-dione (or 5,5-dimethyl-3-anilinocyclohex-2-en-1-one) and ethyl cyanoacetate.

  已经开发了通过靛红与5,5-二甲基环己烷的碱催化多米诺反应合成新的杂环系统，螺环[chromene-4,3'-吲哚]和螺环[吲哚-3,4'-喹啉]的方法。 -1，3-二酮（或5，5-二甲基-3-苯胺基环己二-2-烯-1-酮）和氰基乙酸乙酯。
• Visible-Light-Initiated Oxidative Coupling of Indole and Active Methylene Compounds Using Eosin Y as a Photocatalyst
  作者：Sundaram Singh、Ambuj Kumar Kushwaha、Suresh Kumar Maury、Savita Kumari、Arsala Kamal、Himanshu Kumar Singh、Dhirendra Kumar

  DOI：10.1055/a-1894-8303

  日期：2022.11

  A novel, efficient, mild, and inexpensive photocatalytic approach has been established for the visible-light-initiated oxidative coupling of indole and active methylene compounds using atmospheric air and water as an oxidant in the presence of Eosin Y to give 3-methyleneindolin-2-ones. In this work, only one molecule of malononitrile, ethyl acetoacetate, or dimedone reacts with one molecule of indole

  已经建立了一种新颖、高效、温和且廉价的光催化方法，用于在 Eosin Y 存在下使用大气和水作为氧化剂，在可见光下引发吲哚和活性亚甲基化合物的氧化偶联，得到 3-methyleneindolin-2 -那些。在这项工作中，只有一分子丙二腈、乙酰乙酸乙酯或二甲酮与一分子吲哚反应，但相反，两分子巴比妥酸与一分子吲哚反应。该方法的基本特征是无金属反应、产物收率高、无副产物和使用可再生能源。
• Synthesis of fused 2′-amino-3′-R-spiro-[indole-3,4′-pyran]-2(1H)-ones
  作者：L. A. Shemchuk、V. P. Chernykh、R. G. Red’kin

  DOI：10.1134/s1070428008120117

  日期：2008.12

  An efficient one-pot procedure has been proposed for the synthesis of fused 2'-amino-3'-R-spiro-[indole-3,4'-pyran]-2(1H)-ones via base-catalyzed three-component condensation of isatins with the corresponding nitriles and 1,3-diketones.
• Phosphorus-containing Lewis base catalyzed highly regioselective cyclization of isatin derived electron-deficient alkenes with but-3-yn-2-one
  作者：Zhong Lian、Yin Wei、Min Shi

  DOI：10.1016/j.tet.2012.01.036

  日期：2012.3

  In this paper, we reported that phosphorus-containing Lewis bases catalyzed [4+2] cyclization of N-protected isatin derived electron-deficient alkenes with but-3-yn-2-one could proceed smoothly to give the corresponding dihydropyrano[2,3-b]indoles in good to excellent yields under mild conditions. The substrate scope has been carefully examined and the plausible reaction mechanism has been also proposed. (C) 2012 Elsevier Ltd. All rights reserved.