3-ethyl-1-methyl-3-phenylindolin-2-one | 35524-76-6

• 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: 3-ethyl-1-methyl-3-phenylindolin-2-one
• 英文别名: 3-Ethyl-1-methyl-3-phenylindolin-2-one；3-ethyl-1-methyl-3-phenylindol-2-one
• CAS: 35524-76-6
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: MSTFIOZAKQIYGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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-(2-fluorophenyl)-2-phenylbutanamide 在 potassium tert-butylate 、 potassium hydroxide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 3-ethyl-1-methyl-3-phenylindolin-2-one
  参考文献：
  名称：

  Transition-Metal-Free Synthesis of Oxindoles by Potassium tert-Butoxide-Promoted Intramolecular α-Arylation

  摘要：

  Potassium tert-butoxide-mediated intramolecular alpha-arylations of fluoro- and chloro-substituted anilides provide oxindoles in DMF at 80 degrees C. In this manner, diversely substituted products have been obtained in moderate to high yields.

  DOI：

  10.1021/ol301704z

文献信息

• A benzene-bridged divanadium complex-early transition metal catalyst for alkene alkylarylation with PhI(O₂CR)₂<i>via</i> decarboxylation
  作者：Lei Zhang、Hongfei Zhou、Shaokun Bai、Shaodan Li

  DOI：10.1039/d0dt04295a

  日期：——

  alkene alkylarylation with hypervalent iodine(III) reagents (HIRs) via decarboxylation to generate regioselectively diverse indolinones. Furthermore, the mild nature of this reaction was amenable to a wide range of functionalities on alkenes and HIRs. Mechanistic studies revealed a relay sequence of decarboxylative radical alkylation/radical arylation/oxidative re-aromatization.

  全面研究了苯桥二钒配合物的合成，结构和催化活性。通过以苯为溶剂用石墨烯酸钾（KC 8）还原由β-二酮化支持的（Nacnac）VCl 2（1）（Nacnac =（2,6- i Pr 2 C 6 H 3 NCMe）2 HC）访问苯桥连的倒夹心二钒配合物（μ-η 6：η 6 -C 6 H ^ 6）[V（Nacnac）] 2（图2a），它可催化与高价碘烯烃alkylarylation（III试剂（HIR）通过脱羧生成区域选择性多样的吲哚啉酮。此外，该反应的温和性质适合于烯烃和HIR的多种官能度。机理研究揭示了脱羧自由基烷基化/自由基芳基化/氧化再芳构化的中继序列。
• Oxindole Synthesis by Direct Coupling of C sp 2H and C sp 3H Centers
  作者：Yi-Xia Jia、E. Peter Kündig

  DOI：10.1002/anie.200805652

  日期：——

  An sp2/sp3 get‐together: A novel and efficient method can be used to synthesize 3,3‐disubstitued oxindoles by the direct intramolecular oxidative coupling of an aryl CH and a CH center (see scheme; DMF=N,N‐dimethylformamide).

  sp 2 / sp 3 在一起：可以通过芳基CH和CH中心的直接分子内氧化偶合，使用新颖有效的方法合成3,3-二取代的羟吲哚（参见方案； DMF = N，N-二甲基甲酰胺）。
• Oxindole synthesis <i>via</i> polar–radical crossover of ketene-derived amide enolates in a formal [3 + 2] cycloaddition
  作者：Niklas Radhoff、Armido Studer

  DOI：10.1039/d1sc07134c

  日期：——

  and transition-metal free method for the preparation of valuable and sterically hindered 3,3-disubstituted oxindoles via polar–radical crossover of ketene derived amide enolates. Various easily accessible N-alkyl and N-arylanilines are added to disubstituted ketenes and the resulting amide enolates undergo upon single electron transfer oxidation a homolytic aromatic substitution (HAS) to provide 3,3-disubstituted

  在此，我们介绍了一种简单、有效且不含过渡金属的方法，通过乙烯酮衍生的酰胺烯醇化物的极性-自由基交换来制备有价值的空间位阻3,3-二取代的羟吲哚。将各种容易获得的N-烷基和N-芳基苯胺添加到二取代乙烯酮中，所得酰胺烯醇化物在单电子转移氧化后经历均裂芳族取代 (HAS)，以良好至优异的收率提供 3,3-二取代的羟吲哚。各种取代的苯胺和 3-氨基吡啶参与这种氧化形式的 [3 + 2] 环加成和环状烯酮提供螺吲哚。底物和试剂都很容易获得，并且对官能团的耐受性广泛。
• Copper‐Catalyzed Enantioconvergent Radical C(sp³)−N Cross‐Coupling: Access to α,α‐Disubstituted Amino Acids
  作者：Yu‐Feng Zhang、Jia‐Huan Wang、Ning‐Yuan Yang、Zheng Chen、Li‐Lei Wang、Qiang‐Shuai Gu、Zhong‐Liang Li、Xin‐Yuan Liu

  DOI：10.1002/anie.202302983

  日期：2023.7.3

  Transition‐metal catalyzed enantioconvergent cross‐coupling of tertiary alkyl halides with ammonia offers a rapid avenue to chiral unnatural α,α‐disubstituted amino acids. However, the construction of chiral C−N bonds between tertiary‐carbon electrophiles and nitrogen nucleophiles presented a great challenge owing to steric congestion. We report a copper‐catalyzed enantioconvergent radical C−N cross‐coupling of alkyl halides with sulfoximines (as ammonia surrogates) under mild conditions by employing a chiral anionic N,N,N‐ligand with a long spreading side arm. An array of α,α‐disubstituted amino acid derivatives were obtained with good efficiency and enantioselectivity. The synthetic utility of the strategy has been showcased by the elaboration of the coupling products into different chiral α‐fully substituted amine building blocks.

  摘要 过渡金属催化的叔烷基卤化物与氨的对映转化交叉偶联为获得手性非天然α,α-二取代氨基酸提供了一条捷径。然而，由于立体拥塞，在叔碳亲电体和氮亲核体间构建手性 C-N 键是一个巨大的挑战。我们报告了一种铜催化的对映转化自由基 C-N 交叉偶联反应，该反应是在温和的条件下，利用具有长扩展侧臂的手性阴离子 N,N,N-配体，将烷基卤化物与亚砜亚胺（作为氨代用品）进行交叉偶联。结果以良好的效率和对映选择性获得了一系列 α,α-二取代氨基酸衍生物。通过将偶联产物制成不同的手性 α-完全取代胺结构单元，展示了该策略的合成实用性。
• Iron-Catalyzed Oxidative Arylmethylation of Activated Alkenes Using a Peroxide as the Methyl Source
  作者：Ren-Jie Song、Jin-Heng Li、Jian-Hong Fan、Ming-Bo Zhou、Yu Liu、Wen-Ting Wei、Xuan-Hui Ouyang

  DOI：10.1055/s-0033-1340665

  日期：——

  A novel, simple route for the synthesis of oxindoles is presented via iron-catalyzed oxidative arylmethylation of activated alkenes with peroxides. This work is realized by the use of a peroxide as the methyl source and 1,4-diazabicyclo[2.2.2]octane as the ligand and represents a new access to oxindoles through an alkene oxidative difunctionalization process.