ethyl 2-cyano-2-(2-oxo-2,3-dihydro-1H-3-indolyl)acetate | 99277-32-4

• 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-cyano-2-(2-oxo-2,3-dihydro-1H-3-indolyl)acetate
• 英文别名: ethyl 2-cyano-2-(2-oxoindolin-3-yl)acetate；cyano-(2-oxo-indolin-3-yl)-acetic acid ethyl ester；Cyan-(2-oxo-indolin-3-yl)-essigsaeure-aethylester；Ethyl 2-cyano-2-(2-oxo-1,3-dihydroindol-3-yl)acetate
• CAS: 99277-32-4
• 化学式: C₁₃H₁₂N₂O₃
• 分子量: 244.25
• InChiKey: UEYHKBSBLUNTMT-UHFFFAOYSA-N

物化性质

• 熔点：
  105-110 °C
• 沸点：
  454.1±35.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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-cyano-2-(2-oxo-2,3-dihydro-1H-3-indolyl)acetate 在 sodium hydroxide 作用下， 生成 2-氰基-2-(2-氧代-1,3-二氢吲哚-3-基)乙酸
  参考文献：
  名称：

  728.羟色胺。第四部分。2-3'-氧吲哚基乙胺的合成与反应

  摘要：

  DOI：

  10.1039/jr9580003639
• 作为产物：
  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

文献信息

• Copper-catalyzed hydroboration of alkenyl oxindoles
  作者：Maria Eduarda Contreira、Diogo S. Lüdtke、Angélica V. Moro

  DOI：10.1016/j.tetlet.2018.06.009

  日期：2018.7

  Herein we describe the NHC-Cu(I)-catalyzed hydroboration of alkenyl oxindoles. The corresponding boronates were obtained in good yields, under operationally simple and environmentally friendly conditions, using ethanol as the solvent. Our studies revealed that water-based systems were not very effective. Furthermore, the obtained products are amenable to further elaboration and can be useful to the

  在本文中，我们描述了NHC-Cu（I）催化的烯基羟吲哚的硼氢化。使用乙醇作为溶剂，在操作简单和环境友好的条件下，以高收率获得了相应的硼酸盐。我们的研究表明，水基系统不是很有效。此外，所获得的产物适于进一步加工，并且可用于合成具有生物学相关性的更广泛范围的含羟吲哚的分子。
• Synthetic and Theoretical Studies on the Reduction of Electron Withdrawing Group Conjugated Olefins Using the Hantzsch 1,4-Dihydropyridine Ester
  作者：Simon J. Garden、Cristiano Ruch Werneck Guimarães、Marilza B. Corréa、César Augusto Fernandes de Oliveira、Angelo da Cunha Pinto、Ricardo Bicca de Alencastro

  DOI：10.1021/jo034921e

  日期：2003.11.1

  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.
• Bioreduction of the C C double bond with Pseudomonas monteilii ZMU-T17: one approach to 3-monosubstituted oxindoles
  作者：Jia Zhao、Shuicheng Guan、Xiaojian Zhou、Wenyong Han、Baodong Cui、Yongzheng Chen

  DOI：10.1016/j.tet.2016.04.037

  日期：2016.6

  An efficient whole cell-mediated bioreduction of 3-methylene-2-oxindoles has been developed, affording a range of 3-monosubstituted oxindoles in moderate to good yields (41-82%) with Pseudomonas monteilii ZMU-T17 as biocatalyst. Additionally, a possible reaction pathway for this bioreduction of C=C double bond was proposed. (C) 2016 Elsevier Ltd. All rights reserved.
• 728. Hydroxytryptamines. Part IV. Synthesis and reactions of 2-3′-oxindolylethylamines
  作者：John Harley-Mason、R. F. J. Ingleby

  DOI：10.1039/jr9580003639

  日期：——