1,3-dimethyl-3-(2-methylbenzyl)indolin-2-one

• 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-methylbenzyl)indolin-2-one
• 英文别名: 1,3-Dimethyl-3-[(2-methylphenyl)methyl]indol-2-one；1,3-dimethyl-3-[(2-methylphenyl)methyl]indol-2-one
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: YSRQNBPFAIGJLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  2-((tert-butyldimethylsilyl)oxy)aniline 在 四(三苯基膦)镍 、 potassium tert-butylate 、 sodium hydride 、 三乙胺 、 三苯基膦 、 cesium fluoride 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 1,3-dimethyl-3-(2-methylbenzyl)indolin-2-one
  参考文献：
  名称：

  镍催化的Domino Heck环化/ Suzuki偶联反应合成3,3-二取代的吲哚

  摘要：

  报道了第一个镍催化的多米诺Heck环化/ Suzuki偶联反应，用于合成带有季全碳中心的3,3-二取代的羟吲哚。各种各样的亲电试剂，例如芳基碘化物，溴化物，三氟甲磺酸盐和氯化物，都与反应条件兼容。此外，廉价的芳基酯经过催化的C-O键裂解，也可以用作亲电子试剂。该方法显示出良好的产率和广泛的范围，补充了常规钯基类似物的更实用和可持续的替代方法。

  DOI：

  10.1021/acs.orglett.7b03713

文献信息

• A General Protocol toward Oxindoles Bearing C3‐Allylic Quaternary Stereocenter via Domino Reaction: A Concise Synthesis of Heterocycle‐Fused Indoline Alkaloids
  作者：Hanxiao Yang、Ruoqian Fan、Daheng Wen、Mengmeng Fan、Weiwei Fang

  DOI：10.1002/cjoc.202400324

  日期：2024.10.15

  efficiently catalytic method toward the synthesis of indolin-2-ones featuring an allylic derived C3-quaternary stereocenter via an intramolecular Heck cyclization/Suzuki coupling of N-substituted-N-(2-bromophenyl)acrylamides and organoboron reagents was successfully developed by using a 1,3-bis(2,6-diisopropylphenyl)acenaphthoimidazol-2-ylidene (AnIPr)-ligated oxazoline palladacycle. It enabled a very broad

  通过N-取代-N- (2-溴苯基)丙烯酰胺和有机硼试剂的分子内 Heck 环化/Suzuki 偶联，成功开发了一种有效催化合成二氢吲哚-2-酮的方法，该方法具有烯丙基衍生的 C3-季立构中心1,3-双(2,6-二异丙基苯基)苊并咪唑-2-亚基 (AnIPr)-连接的恶唑啉钯环。它实现了非常广泛的底物范围，可容纳不同的官能团、电子特性和空间体积。值得注意的是，它揭示了通过相同的中间体 3-烯丙基-1,3-二甲基二氢吲哚-2-一构建多种杂环稠合二氢吲哚生物碱的巨大潜力。
• Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling
  作者：Kuai Wang、Zhengtian Ding、Zhijun Zhou、Wangqing Kong

  DOI：10.1021/jacs.8b08190

  日期：2018.10.3

  A Ni-catalyzed enantioselective reductive diarylation of activated alkenes by domino cyclizative/ cross-coupling of two aryl bromides is developed. This reaction proceeds under very mild conditions and shows broad substrate scope, without requiring the use of preformed organometallic reagents. Moreover, this approach provides direct access to various bis-heterocycles bearing all-carbon quaternary centers in synthetically useful yields (up to 81%) with excellent enantioselectivity (>30 examples, 90-99% ee).
• Copper(I)-Catalyzed Aryl or Vinyl Addition to Electron-Deficient Alkenes Cascaded by Cationic Cyclization
  作者：Bing Zhou、Wei Hou、Yaxi Yang、Huijin Feng、Yuanchao Li

  DOI：10.1021/ol500033w

  日期：2014.3.7

  An exoselective copper-catalyzed arylation and vinylation-carbocyclization of electron-deficient alkenes was developed to provide rapid and efficient access to a variety of functionalized 3,3-disubstituted oxindoles. With this method, a highly efficient and concise formal synthesis of (+/-)-physostigmine and (+/-)-physovenine has been completed.
• Copper-Catalyzed Diarylation of Activated Alkenes with Diaryliodonium Salts
  作者：Jianwei Han、Limin Wang、Yang Yang、Xunshen Wu、Song Mao、Jianjun Yu

  DOI：10.1055/s-0033-1339004

  日期：——

  Cu(OTf)(2)-catalyzed diarylation of activated alkenes by using diaryliodonium(III) salts has been developed. With this method, arylated oxindoles can be easily accessed in good yields. Insights into the mechanism of copper-catalyzed arylations are discussed, and the findings are expected to help increase the level of understanding of catalytic arylations with diaryliodonium salts.
• Synthesis of 3,3-Disubstituted Oxindoles by Visible-Light-Mediated Radical Reactions of Aryl Diazonium Salts with N-Arylacrylamides
  作者：Weijun Fu、Fengjuan Xu、Yuqin Fu、Mei Zhu、Jiaqi Yu、Chen Xu、Dapeng Zou

  DOI：10.1021/jo401894b

  日期：2013.12.6

  A mild and efficient visible-light-mediated diarylation of N-arylacrylamides with aryl diazonium salts under mild conditions has been developed. This method provides convenient access to a variety of useful 3,3-disubstituted oxindoles by constructing two C-C bonds in one step.