diethyl 2-(1H-indol-2-yl)malonate | 61417-35-4

• 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: diethyl 2-(1H-indol-2-yl)malonate
• 英文别名: indol-2-yl-malonic acid diethyl ester；(2-Indolyl)malonsaeure-diethylester；Diethyl (1H-indol-2-yl)propanedioate；diethyl 2-(1H-indol-2-yl)propanedioate
• CAS: 61417-35-4
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: HQEIICOUHZBIRA-UHFFFAOYSA-N

物化性质

• 熔点：
  67-68 °C
• 沸点：
  410.1±30.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Diethyl [(2-nitrophenyl)acetyl]propanedioate 以50%的产率得到
  参考文献：
  名称：

  GUDJONS J.; OEHL R.; ROSENMUND P., CHEM. BER. , 1976, 109, NO 10, 3282-3291

  摘要：

  DOI：

文献信息

• Investigation of Straightforward, Photoinduced Alkylations of Electron‐Rich Heterocompounds with Electron‐Deficient Alkyl Bromides in the Sole Presence of 2,6‐Lutidine
  作者：Elina Fuks、Laura Huber、Thea Schinkel、Oliver Trapp

  DOI：10.1002/ejoc.202001003

  日期：2020.10.22

  photosensitizer: We introduce a method for selective photoinduced alkylations of electron‐rich heterocompounds with electron‐deficient allyl bromides in the presence of 2,6‐lutidine at 365 or 405 nm. Mechanistic investigations reveal that a colored intermediate formed from 2,6‐lutidine and alkyl bromide is involved in the photoactivation. Our approach uses commercially available reagents and a straightforward

  无需复杂的光敏剂：我们介绍了一种在365或405 nm处有2,6-核苷存在的情况下，用缺电子的烯丙基溴对富电子的杂化合物进行选择性光诱导烷基化的方法。机理研究表明，由2,6-二甲基吡啶和烷基溴形成的有色中间体参与了光活化。我们的方法使用市售试剂和简单明了的方案。
• Visible-Light Photocatalytic Double C–H Functionalization of Indoles: A Synergistic Experimental and Computational Study
  作者：Jørn Hansen、Uranbaatar Erdenebileg、Taye Demissie

  DOI：10.1055/s-0036-1588719

  日期：——

  C–H functionalization of indoles. The reaction affords 2,3-difunctionalized indoles in up to 84% yield, but the reaction rate depends strongly on electronic substituent effects. Mechanistic DFT studies and control experiments suggest that the secondary functionalization occurs through an independent photocatalytic oxidation of bromide ions formed during the reaction to generate molecular bromine capable

  本文公开了一种新型的吲哚的可见光光催化双 C-H 功能化。该反应以高达 84% 的产率提供 2,3-双官能化吲哚，但反应速率很大程度上取决于电子取代基的影响。机械 DFT 研究和控制实验表明，二次官能化是通过对反应过程中形成的溴离子进行独立的光催化氧化而发生的，以生成能够亲电 C-3 溴化的分子溴。
• Visible light/Ir(III) photocatalytic initiation of xanthate-based radical-chain reactions: Xanthate group transfer and oxidative addition to aromatic systems
  作者：Pedro López-Mendoza、John E. Díaz、Alix E. Loaiza、Luis D. Miranda

  DOI：10.1016/j.tet.2018.04.079

  日期：2018.9

  The protocol can be used in classical xanthate-based inter- and intra-molecular group transfer reactions and oxidative radical addition to several heteroaromatic systems. The process does not require high temperature and reactions are cleaner compared with the traditional peroxide initiation. In the oxidative addition to aromatic systems, the oxidation process is part of the catalytic cycle and does

  描述了使用Ir（ppy）3和蓝色LED辐照，从O-乙基黄药中的光催化氧化还原产生自由基，从而在光氧化还原催化下产生亲电子自由基。该协议可用于经典的基于黄药的分子间和分子内基团转移反应以及向多个杂芳族体系中添加氧化自由基。该方法不需要高温，并且与传统的过氧化物引发相比，反应更清洁。在芳族体系的氧化加成中，氧化过程是催化循环的一部分，不需要化学计量的氧化剂（例如DLP），而该化学计量的氧化剂尤其难以从产物中分离出来。
• Involving Single-Atom Silver(0) in Selective Dehalogenation by AgF under Visible-Light Irradiation
  作者：Wenli Wu、Enxin Cui、Yun Zhang、Chen Zhang、Feng Zhu、Chen-Ho Tung、Yifeng Wang

  DOI：10.1021/acscatal.9b01929

  日期：2019.7.5

  The dehalogenation-arylation and the hydro-dehalogenation of various types of organic halides are selectively realized using AgF and visible light without any organic additives under mild conditions. Single-atom silver(0) (denoted as SAAg) serves as the catalytically active center, and the TOF of SAAg reaches 6000 h(-1). This elusive activity of Ag is beyond that expected from its ionic, nano, or bulk forms.