3-benzyl-1,3-dimethyl-5-methoxy-2-oxoindoline | 123273-05-2

• 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-benzyl-1,3-dimethyl-5-methoxy-2-oxoindoline
• 英文别名: 3-benzyl-5-methoxy-1,3-dimethylindolin-2-one；3-Benzyl-5-methoxy-1,3-dimethylindol-2-one
• CAS: 123273-05-2
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: QPJVXWYLPIPYTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基-P-氨基苯甲醚 在 碳酸氢钠 、 三乙胺 、 copper(l) chloride 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 3-benzyl-1,3-dimethyl-5-methoxy-2-oxoindoline
  参考文献：
  名称：

  Copper(I)-Catalyzed Aryl or Vinyl Addition to Electron-Deficient Alkenes Cascaded by Cationic Cyclization

  摘要：

  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.

  DOI：

  10.1021/ol500033w

文献信息

• Copper-catalyzed bis-arylations of alkenes leading to oxindole derivatives
  作者：Liangliang Shi、Yuyuan Wang、Haijun Yang、Hua Fu

  DOI：10.1039/c4ob00576g

  日期：——

  A simple and practical copper-catalyzed approach to oxindole derivatives by copper-catalyzed bis-arylation of N-alkyl-N-phenylacrylamides with diaryliodonium triflates has been developed under mild conditions, and the method is of tolerance towards some functional groups in the substrates.

  一个简单且实用的铜催化方法已经被开发出来，用于在温和条件下通过铜催化的二芳基化反应合成吲哚衍生物，该方法对底物中的一些官能团具有耐受性。
• Copper-Catalyzed Oxidative Electrophilic Carbofunctionalization of Acrylamides for the Synthesis of Oxindoles
  作者：Guo Tang、Xueqin Li、Jian Xu、Pengbo Zhang、Yuzhen Gao、Ju Wu、Yufen Zhao

  DOI：10.1055/s-0034-1378354

  日期：——

  A novel and efficient copper-catalyzed tandem oxidative cyclization of arylacrylamides with diaryliodonium salts is reported. This reaction provides a novel approach for the synthesis of oxindoles and various functional groups were well tolerated.

  报道了一种新型有效的铜催化的芳基丙烯酰胺与二芳基碘盐的串联氧化环化反应。该反应为羟吲哚的合成提供了一种新方法，并且各种官能团具有良好的耐受性。
• Asymmetric synthesis of oxindoles containing a quaternary stereogenic centre by catalytic O/C-carboxyl rearrangement
  作者：Muhammad Ismail、Huy V. Nguyen、Gennadiy Ilyashenko、Majid Motevalli、Christopher J. Richards

  DOI：10.1016/j.tetlet.2009.08.122

  日期：2009.11

  A catalysed O/C-carboxyl rearrangement generates the all-carbon stereogenic centre in phenyl 1,3-dimethyl-5-methoxy-2-oxoindoline-3-carboxylate (up to 57% ee). Crystallisation and removal of racemic crystals enhance the ee to 95%. The X-ray crystal structure of the cobalt metallocene–pyrrolidinopyridine nucleophilic catalyst employed is reported.

  催化的O / C-羧基重排在苯基1,3-二甲基-5-甲氧基-2-氧代吲哚啉-3-羧酸酯（至多57％ee）中生成全碳立构中心。结晶和外消旋晶体的去除将ee提高到95％。报道了所使用的钴金属茂-吡咯烷基二吡啶亲核催化剂的X射线晶体结构。
• <i>Endo</i>/<i>Exo</i>-Controllable Photocyclization by EnT-SET-Switch
  作者：Xian-Peng Cai、Bin-Hong Han、Fu-Tong Cen、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.orglett.3c00837

  日期：2023.4.28

  CBZ6, a redox-neutral non-donor–acceptor-type organo-photocatalyst, presents a strong reductive potential with an oxidative potential of −2.16 V (vs SCE). It can work as a photosensitizer for both single-electron transfer and triplet energy transfer processes. This feature enables site-selective control in the intramolecular hydroarylation of acrylamides. Both 5-exo-trig and 6-endo-trig cyclization

  CBZ6是一种氧化还原中性非供体-受体型有机光催化剂，具有很强的还原电位，氧化电位为 -2.16 V（相对于 SCE）。它可以作为单电子转移和三线态能量转移过程的光敏剂。此功能可以在丙烯酰胺的分子内加氢芳基化中进行位点选择性控制。5- exo -trig 和 6- endo -trig 环化产物均可在温和条件下区域特异性制备。不涉及过渡金属、含卤素试剂或额外的还原剂或氧化剂。该过程为一系列羟吲哚和二氢喹啉酮提供了一种简洁且环境可持续的途径。
• 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.