1-methyl-3-phenethylindolin-2-one | 1232167-50-8

• 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-methyl-3-phenethylindolin-2-one
• 英文别名: 1-methyl-3-(2-phenylethyl)-3H-indol-2-one
• CAS: 1232167-50-8
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: MFOHUIQEWAITGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 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：

  (±)-tert-butyl 2-(methyl(phenyl)carbamoyl)-4-phenylbutanoate 在 potassium tert-butylate 、 copper(II) acetate monohydrate 、 苯甲醚 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-methyl-3-phenethylindolin-2-one
  参考文献：
  名称：

  Preparation of 3-Alkylated Oxindoles from N-Benzyl Aniline via a Cu(II)-Mediated Anilide Cyclization Process

  摘要：

  DOI：

  10.15227/orgsyn.089.0438

文献信息

• <i>C</i>-Alkylation of <i>N</i>-alkylamides with styrenes in air and scale-up using a microwave flow reactor
  作者：Joshua P. Barham、Souma Tamaoki、Hiromichi Egami、Noriyuki Ohneda、Tadashi Okamoto、Hiromichi Odajima、Yoshitaka Hamashima

  DOI：10.1039/c8ob02282h

  日期：——

  N-alkylamides with styrenes is reported, proceeding in ambient air/moisture to give arylbutanamides and pharmaceutically-relevant scaffolds in excellent mass balance. Various amide and styrene derivatives were tolerated, rapidly affording molecular complexity in a single step; thus highlighting the future utility of this transformation in the synthetic chemistry toolbox. Reaction scalability (up to

  Ç的烷基化Ñ -alkylamides与苯乙烯报道，在环境空气中前进/水分，得到arylbutanamides和在良好的质量平衡的药学上相关的支架。可以耐受各种酰胺和苯乙烯衍生物，只需一步即可快速提供分子复杂性。因此，突出了这种转变在合成化学工具箱中的未来实用性。作为使用苯乙烯连续流动的C-烷基化反应的第一个实例，使用微波流反应器证明了反应可扩展性（高达65 gh -1产物）。
• 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。
• Preparation of 3-Alkyl-Oxindoles by Copper(II)-Mediated C-H, Ar-H Coupling Followed by Decarboxyalkylation
  作者：Richard Taylor、David. Pugh、Johannes Klein、Alexis Perry

  DOI：10.1055/s-0029-1219392

  日期：2010.4

  A novel route for the conversion of anilides into 3-alkyl-oxindoles is described in which a copper(II)-mediated cyclization process is followed by an acid-mediated decarboxyalkylation. Scope and limitation studies are reported together with a telescoped variant which incorporates in situ N-deprotection.

  介绍了一种将苯胺转化为 3-烷基-氧吲哚的新方法，其中先进行铜（II）介导的环化反应，然后再进行酸介导的脱羧基烷基化反应。报告了范围和局限性研究，以及结合了原位 N-脱保护的伸缩变体。
• Boryl Radical-Promoted Dehydroxylative Alkylation of 3-Hydroxyoxindole Derivatives
  作者：Tesfaye Tebeka Simur、Tian-Yu Peng、Yi-Feng Wang、Xiu-Wei Wu、Feng-Lian Zhang

  DOI：10.1021/acs.orglett.3c00521

  日期：——

  alkylation of 3-hydroxy-oxindole derivatives is achieved. The reaction starts from addition of 4-dimethylaminopyridine (DMAP)-boryl radical to the amide carbonyl oxygen atom, which induces a spin-center shift process to promote the C–O bond cleavage. The elimination of a hydroxide anion from a free hydroxy group is also accomplished. Capture of the generated carbon radical with alkenes furnishes a variety

  实现了硼自由基促进的 3-羟基-羟吲哚衍生物的脱羟基烷基化。该反应从将 4-二甲氨基吡啶 (DMAP)-硼基添加到酰胺羰基氧原子开始，这会引发自旋中心移动过程以促进 C-O 键断裂。还完成了从游离羟基中消除氢氧根阴离子。用烯烃捕获生成的碳自由基可提供各种 C-3 烷基化羟吲哚。该方法操作简单，底物适用范围广。
• Rhenium-Catalyzed Acceptorless Dehydrogenative Coupling via Dual Activation of Alcohols and Carbonyl Compounds
  作者：Hongming Jin、Jin Xie、Changduo Pan、Zhengbo Zhu、Yixiang Cheng、Chengjian Zhu

  DOI：10.1021/cs400572q

  日期：2013.10.4

  The rhenium hetaphydride complex was found to be a versatile, homogeneous catalyst for dehydrogenative functionalization of alcohol. The dehydrogenative C-C coupling of alcohols and carbonyl compounds was carried out in the absence Of base and hydrogen acceptors to afford a series of alpha,beta-unsaturated carbonyl compounds. A possible dual activation pathway was proposed by mechanistic investigations.