1,3-dimethyl-3-(2-oxobutyl)indolin-2-one | 1630982-55-6

• 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: 1,3-dimethyl-3-(2-oxobutyl)indolin-2-one
• 英文别名: 1,3-Dimethyl-3-(2-oxobutyl)indol-2-one；1,3-dimethyl-3-(2-oxobutyl)indol-2-one
• CAS: 1630982-55-6
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: HXQZCJCOVUBILK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基苯胺 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 1,3-dimethyl-3-(2-oxobutyl)indolin-2-one
  参考文献：
  名称：

  肟酯的光催化CC键活化用于酰基自由基的产生和应用

  摘要：

  据报道，有一种通过选择性C–C键活化从肟酯生成酰基的统一策略。在可见光照射下，发生了从fac -Ir（ppy）3到相关肟的单电子转移，接着是快速的C-C键β片段产生芳基和脂族酰基基团，随后被各种Michael受体捕获。更有趣的是，单电子转移能够通过就地形成环丁烷的烯酮中间体与激发的fac -Ir（ppy）3的能量转移耦合。

  DOI：

  10.1021/acs.orglett.9b01338

文献信息

• Iron-Catalyzed Oxidative 1,2-Carboacylation of Activated Alkenes with Alcohols: A Tandem Route to 3-(2-Oxoethyl)indolin-2-ones
  作者：Xuan-Hui Ouyang、Ren-Jie Song、Jin-Heng Li

  DOI：10.1002/ejoc.201400043

  日期：2014.6

  natural products. A new oxidative tandem route to the assembly of 3-(2-oxoethyl)indolin-2-ones from N-arylacrylamides and alcohols has been established by using inexpensive and environmentally benign iron catalysts and peroxides. In the presence of Fe(OAc)2 and tert-butyl hydroperoxide, a variety of arylacrylamides underwent the oxidative 1,2-carboacylation reaction with alcohols to give the corresponding

  羟吲哚是重要的杂环化合物，广泛存在于各种药剂和天然产物中。通过使用廉价且对环境无害的铁催化剂和过氧化物，建立了从 N-芳基丙烯酰胺和醇组装 3-(2-oxoethyl)indolin-2-ones 的新氧化串联途径。在 Fe(OAc)2 和叔丁基过氧化氢存在下，各种芳基丙烯酰胺与醇发生氧化 1,2-碳酰化反应，得到相应的 3-(2-oxoethyl)indolin-2-ones产量。
• Metal-free visible-light-driven cascade cyclization reaction to synthesize 2-oxindoles <i>via</i> benzoyl and phenylsulfinyl radicals with acrylamide derivatives
  作者：Xin Sun、Jing-Ping Zhu、Qing-Chuang Qiu、Ya-Li He、Da-Rong Hu、Xin-Ling Li、Gui-Ping Lu、Ying-Hui Yuan、Xiang-Fei Zhang、Xiaobo Xu、Miao Yu、Bin Wu

  DOI：10.1039/d2ob01256a

  日期：——

  visible-light-driven cascade cyclization reaction to synthesize 3-methyl-3-acetophenone-2-oxindoles and 3-methyl-3-(methylsulfonyl)benzene-2-oxindoles in yields up to 96% and 99%, via benzoyl and phenylsulfinyl radicals with acrylamide derivatives is reported, respectively. Extensive studies, including gram-scale, radical capture and isotope experiments, were performed to indicate that the reaction may involve a radical

  无金属可见光驱动的级联环化反应合成 3-甲基-3-苯乙酮-2-羟吲哚和 3-甲基-3-(甲基磺酰基)苯-2-羟吲哚的产率高达 96% 和 99%，分别报道了通过苯甲酰基和苯亚磺酰基自由基与丙烯酰胺衍生物。进行了广泛的研究，包括克级、自由基捕获和同位素实验，以表明该反应可能涉及自由基过程。
• Synthetic utility of functionalized alkylsilyl peroxides for Fe-catalyzed and visible-light-promoted radical transformation
  作者：Jiahao Liu、Shiyong Liu、Zhe Wang、Terumasa Kato、Yan Liu、Keiji Maruoka

  DOI：10.1039/d3sc06857a

  日期：——

  α-Keto-, β-acetoxy- and β-amidoalkylsilyl peroxides are prepared from various precursors and utilized for Fe-catalyzed and visible-light-promoted radical functionalization with coupling partners under mild conditions with a broad substrate scope.

  α-酮基-、β-乙酰氧基-和β-酰胺基烷基甲硅烷基过氧化物由各种前体制备，并在温和条件下与偶联伙伴一起用于 Fe 催化和可见光促进的自由基官能化，具有广泛的底物范围。
• Transition-Metal-Free Synthesis of Carbonyl-Containing Oxindoles from <i>N</i>-Arylacrylamides and α-Diketones via TBHP- or Oxone-Mediated Oxidative Cleavage of C(sp²)–C(sp²) Bonds
  作者：Ming-Zhong Zhang、Peng-Yi Ji、Yu-Feng Liu、Can-Cheng Guo

  DOI：10.1021/acs.joc.5b01977

  日期：2015.11.6

  Carbonyl-containing oxindoles can be prepared from N-arylacrylamides and alpha-diketones by TBHP- or oxone (KHSO5)-mediated C(sp(2))-C(sp(2)) bond cleavage and new C(sp(2))-C(sp(3)) bond formation. This methodology is characterized by its simple and transition-metal-free conditions and good functional group compatibility utilizing inexpensive and readily available reagents, thus providing a practical and efficient approach to an important class of 3-(2-oxoethyl)indolin-2-ones which are highly valued synthetic intermediates of biologically active molecules. In this transformation, alkylcarbonyl-containing oxindoles were obtained in majority when N-arylacrylamides reacted with asymmetric aliphatic/aromatic alpha-diketones. On the basis of the preliminary experiments, a plausible mechanism of this transformation is disclosed.
• Photocatalytic C–C Bond Activation of Oxime Ester for Acyl Radical Generation and Application
  作者：Xiuwei Fan、Tao Lei、Bin Chen、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1021/acs.orglett.9b01338

  日期：2019.6.7

  strategy to generate acyl radical from oxime ester via selective C–C bond activation is reported. Under visible-light irradiation, single-electron transfer from fac-Ir(ppy)3 to related oxime takes place followed by a fast β-fragment of C–C bond to yield aryl and aliphatic acyl radicals, subsequently captured by diverse Michael acceptors. More interestingly, the single-electron transfer enables coupling

  据报道，有一种通过选择性C–C键活化从肟酯生成酰基的统一策略。在可见光照射下，发生了从fac -Ir（ppy）3到相关肟的单电子转移，接着是快速的C-C键β片段产生芳基和脂族酰基基团，随后被各种Michael受体捕获。更有趣的是，单电子转移能够通过就地形成环丁烷的烯酮中间体与激发的fac -Ir（ppy）3的能量转移耦合。