5-methoxy-1,3-dimethyl-3-neopentylindolin-2-one | 1382847-25-7

• 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: 5-methoxy-1,3-dimethyl-3-neopentylindolin-2-one
• CAS: 1382847-25-7
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: TTYVQVBXQJMHFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-甲基-P-氨基苯甲醚 在 cerium(III) chloride 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 14.0h， 生成 5-methoxy-1,3-dimethyl-3-neopentylindolin-2-one
  参考文献：
  名称：

  N-芳基丙烯酰胺和 N-丙烯酰基-2-芳基苯并咪唑的光诱导铈介导的脱羧烷基化级联环化

  摘要：

  在有氧条件下，利用廉价的铈催化剂和原料羧酸作为烷基自由基替代物，开发了一种操作简单且有效的光诱导脱羧自由基烷基化/环化。这种催化歧管允许直接获得范围广泛的季 C3 烷基化羟吲哚和苯并 [4,5] 咪唑并 [2,1- a ] 异喹啉-6(5 H )-一种衍生物，提供出色的官能团耐受性。

  DOI：

  10.1002/asia.202300028

文献信息

• Metal-free cascade oxidative decarbonylative alkylarylation of acrylamides with aliphatic aldehydes: a convenient approach to oxindoles via dual C(sp²)–H bond functionalization
  作者：Luo Yang、Wen Lu、Wang Zhou、Feng Zhang

  DOI：10.1039/c6gc00362a

  日期：——

  A convenient metal-free cascade oxidative decarbonylative alkylarylation of acrylamides with aliphatic aldehydes to provide quaternary oxindoles is developed.

  开发了一种方便的无金属的丙烯酰胺与脂族醛的级联氧化脱羰烷基芳基化反应，以提供季吲哚。
• N-(Acyloxy)phthalimides as tertiary alkyl radical precursors in the visible light photocatalyzed tandem radical cyclization of N-arylacrylamides to 3,3-dialkyl substituted oxindoles
  作者：Qi Tang、Xiubin Liu、Sheng Liu、Hongqi Xie、Wei Liu、Jianguo Zeng、Pi Cheng

  DOI：10.1039/c5ra17292f

  日期：——

  light promoted tandem radical cyclization of N-arylacrylamides with N-(acyloxy)phthalimides to 3,3-dialkyl substituted oxindoles was developed. In the presence of a photocatalyst Ru(bpy)3Cl2·6H2O, an organic base i-Pr2NEt and the irradiation of a 25 W compact fluorescence bulb at room temperature, N-(acyloxy)phthalimides may be used as a masking group for tertiary alkyl radicals. This tandem radical

  可见光促进了N-芳基丙烯酰胺与N-（酰氧基）邻苯二甲酰亚胺串联生成3,3-二烷基取代的羟吲哚的串联自由基环化反应。在光催化剂Ru（bpy）3 Cl 2 ·6H 2 O，有机碱i-Pr 2 NEt的存在和室温下25 W紧凑型荧光灯的照射下，可以使用N-（酰氧基）邻苯二甲酰亚胺叔烷基的掩蔽基团。该串联自由基反应在室温下顺利进行，得到3，3-二烷基取代的羟吲哚，避免使用过氧化物。
• Transition-metal-free alkylation strategy: facile access to alkylated oxindoles <i>via</i> alkyl transfer
  作者：Wen-Qin Yu、Jian-Hong Fan、Pu Chen、Bi-Quan Xiong、Jun Xie、Ke-Wen Tang、Yu Liu

  DOI：10.1039/d2ob00019a

  日期：——

  The transition-metal-free alkylation/cyclization of activated alkenes using Hantzsch ester derivatives as effective alkyl reagents is described. A wide variety of valuable oxindoles was constructed in a single step with excellent selectivity. The reaction occurs through the formation of alkyl radical species followed by the tandem addition/annulation of olefins under oxidative conditions. This protocol

  描述了使用 Hantzsch 酯衍生物作为有效烷基试剂的活化烯烃的无过渡金属烷基化/环化。在一个步骤中以优异的选择性构建了多种有价值的羟吲哚。该反应通过形成烷基自由基物质，然后在氧化条件下串联烯烃的加成/环化而发生。该协议有望为开发 Hantzsch 酯在有机合成中的新颖高效应用提供灵感。
• Aliphatic Acylhydrazides as Effective Alkylating Agents for the Copper-Catalyzed Oxidative Cyclization of N-Arylacrylamides
  作者：Dong Xie、Ren-Gui Tian、Jia-Jia Liao、Shi-Kai Tian

  DOI：10.1055/a-2052-3331

  日期：——

  acylhydrazides as alkylating agents has been demonstrated in the copper-catalyzed tandem alkylation/cyclization of N-arylacrylamides. A range of aliphatic acylhydrazides smoothly participated in the oxidative 5-exo-trig cyclization of N-arylacrylamides with CuCO3 as the catalyst and DTBP as the oxidant, delivering structurally diverse 3,3-dialkyloxindoles in moderate to good yields. This study paves the way

  在N -芳基丙烯酰胺的铜催化串联烷基化/环化中，已经证明了一种前所未有的使用容易获得的脂肪族酰肼作为烷基化剂的方法。一系列脂肪族酰肼以 CuCO 3为催化剂，DTBP 为氧化剂顺利参与N-芳基丙烯酰胺的氧化 5- exo -trig 环化反应，以中等至良好的收率提供结构多样的 3,3-二烷基羟吲哚。该研究为脂肪族酰肼作为烷基自由基前体的合成应用铺平了道路。
• Organocatalyzed arylalkylation of activated alkenes via decarboxylation of PhI(O2CR)2: efficient synthesis of oxindoles
  作者：Tao Wu、Hao Zhang、Guosheng Liu

  DOI：10.1016/j.tet.2012.03.051

  日期：2012.7

  A novel organocatalyzed arylalkylation of activated alkenes has been developed. This reaction was initiated from the decomposition of PhI(O2CR)(2) to generate alkyl radical, followed by addition to alkenes. Then the formed radical was trapped by aromatic ring to generate the cyclized products. This method presents an efficient road to synthesis of a variety of oxindoles. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.