1,3-dimethyl-3-(4-methylphenethyl)indolin-2-one | 1491270-75-7

• 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-(4-methylphenethyl)indolin-2-one
• 英文别名: 1,3-Dimethyl-3-[2-(4-methylphenyl)ethyl]indol-2-one；1,3-dimethyl-3-[2-(4-methylphenyl)ethyl]indol-2-one
• CAS: 1491270-75-7
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: YQFIUFSUVPYTKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-甲基苯胺 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 碳酸氢钠 、 potassium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 48.0h， 生成 1,3-dimethyl-3-(4-methylphenethyl)indolin-2-one
  参考文献：
  名称：

  Oxidant-Free Rhodium(I)-Catalyzed Difunctionalization of Acrylamide: An Efficient Approach To Synthesize Oxindoles

  摘要：

  The first rhodium(I)-catalyzed difunctionalization of arylacrylamides. to synthesize oxindoles is developed, and it does not require the asistance of an oxidant. This method provides an efficient approach to generate various useful functionalized oxindoles, some of which cannot be easily accessed by previous approaches.

  DOI：

  10.1021/acs.orglett.5b00732

文献信息

• Palladium-Catalyzed Alkylarylation of Acrylamides with Unactivated Alkyl Halides
  作者：Hua Wang、Li−Na Guo、Xin-Hua Duan

  DOI：10.1021/acs.joc.5b02433

  日期：2016.2.5

  An efficient palladium-catalyzed alkylarylation of acrylamides with unactivated alkyl halides has been developed. This method is highlighted by its broad substrate scope and excellent functional group tolerance. In addition to alkyl halides, fluoroalkyl halides and benzyl bromides also participated well in this transformation. A detailed mechanistic investigation suggests that a radical pathway is

  已经开发了一种有效的钯催化丙烯酰胺与未活化的烷基卤化物的烷基芳基化反应。该方法以其广泛的底物范围和出色的官能团耐受性而著称。除了卤代烷之外，氟代卤代烷和苄基溴也很好地参与了这一转化。详细的机械研究表明，自由基途径可能与环化过程有关。
• Free-Radical Cascade Alkylarylation of Alkenes with Simple Alkanes: Highly Efficient Access to Oxindoles via Selective (sp³)C–H and (sp²)C–H Bond Functionalization
  作者：Zejiang Li、Ye Zhang、Lizhi Zhang、Zhong-Quan Liu

  DOI：10.1021/ol4032478

  日期：2014.1.17

  A copper-catalyzed alkylarylation of alkenes with simple alkanes was achieved, which not only provided an efficient method to prepare various alkyl-substituted oxindoles, but also represented a novel strategy for selective sp3 C–H functionalization/C–C bond formation via a free-radical cascade process. Additionally, selective activation of unactivated (sp3)C–H and (sp2)C–H bonds by one single step

  铜与简单的烷烃催化的烯烃的烷基芳基化反应不仅为制备各种烷基取代的羟吲哚提供了一种有效的方法，而且还代表了一种通过a选择性sp 3 C–H官能化/ C–C键形成的新策略。自由基级联过程。此外，在该系统中，仅一步即可选择性激活未激活的（sp 3）CH键和（sp 2）CH键，这也将为提高CH键功能化的效率提供一种新的策略。
• Nickel-Catalyzed Alkylarylation of Activated Alkenes with Benzyl-amines via C−N Bond Activation
  作者：Hui Yu、Bin Hu、Hanmin Huang

  DOI：10.1002/chem.201800543

  日期：2018.5.17

  A nickel‐catalyzed alkylarylation of active alkenes with tertiary benzylamines was achieved by charge‐transfer‐complex promoted C−N bond activation. The reaction proceeded through initial Ni‐catalyzed C−N bond activation, followed by sequential radical addition, redox and proton abstraction with cleaved amine moiety in the absence of oxidant, and provides an efficient method to prepare various alkyl‐substituted

  通过电荷转移络合物促进的C-N键活化，实现了镍与叔苄基胺催化的活性烯烃烷基芳基化反应。该反应通过最初的Ni催化的C-N键活化而进行，然后在不存在氧化剂的情况下依次进行自由基加成，氧化还原和带有裂解的胺部分的质子提取，为制备各种烷基取代的羟吲哚和二氢喹啉酮提供了一种有效的方法。产量。
• Discovery of an Oxidative System for Radical Generation from Csp³–H Bonds: A Synthesis of Functionalized Oxindoles
  作者：Ming-Zhong Zhang、Wan-Ting Li、Yuan-Yuan Li、Qi Wang、Chong Li、Yan-Hao Liu、Jin-Xing Yin、Xin Yang、Huisheng Huang、Tieqiao Chen

  DOI：10.1021/acs.joc.1c02032

  日期：2021.11.5

  cycloalkanes, and haloalkanes were selectively activated to generate the corresponding C-centered radicals, which could be further captured by N-arylacrylamides to deliver the valuable functionalized oxindoles. Good functional group tolerance was demonstrated. The useful polycarbonyl compound and esters were also modified with the strategy. Moreover, the combination can also be applied to the practical coupling

  开发了一种在无金属和无有机过氧化物条件下从 Csp 3 -H 键生成自由基的简便且通用的方法。通过结合安全的过硫酸盐和低毒的季铵盐，多种 Csp 3 -H 化合物，包括醚、（杂）芳香族/脂肪族酮、烷基苯、烷基杂环、环烷烃和卤代烷烃被选择性地激活以生成相应的以 C 为中心的化合物。自由基，可以被N进一步捕获-芳基丙烯酰胺以提供有价值的官能化羟吲哚。证明了良好的官能团耐受性。有用的多羰基化合物和酯也用该策略改性。此外，该组合还可应用于简单卤代烷烃与N-羟基邻苯二甲酰亚胺（NHPI）之间的实际偶联。
• Oxidative 1,2-difunctionalization of activated alkenes with benzylic C(sp3)–H bonds and aryl C(sp2)–H bonds
  作者：Ming-Bo Zhou、Cheng-Yong Wang、Ren-Jie Song、Yu Liu、Wen-Ting Wei、Jin-Heng Li

  DOI：10.1039/c3cc45861j

  日期：——

  DTBP (di-tert-butyl peroxide) is utilized to mediate oxidative 1,2-difunctionalization of activated alkenes with an aryl C(sp(2))-H bond and a benzylic C(sp(3))-H bond for the synthesis of functionalized oxindoles. This reaction is a new organomediated strategy for alkene difunctionalization facilitated by Lewis acids.

  DTBP（二叔丁基过氧化物）用于介导具有芳基C（sp（2））-H键和苄基C（sp（3））-H键的活化烯烃的氧化1,2-双官能化合成功能化的吲哚。该反应是路易斯酸促进的烯烃双官能化的新的有机介导策略。