3-(2,2-difluoroethyl)-5-methoxy-1,3-dimethylindolin-2-one | 1587689-00-6

• 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-(2,2-difluoroethyl)-5-methoxy-1,3-dimethylindolin-2-one
• 英文别名: 3-(2,2-Difluoroethyl)-5-methoxy-1,3-dimethylindol-2-one；3-(2,2-difluoroethyl)-5-methoxy-1,3-dimethylindol-2-one
• CAS: 1587689-00-6
• 化学式: C₁₃H₁₅F₂NO₂
• 分子量: 255.264
• InChiKey: HXHFYSOXOUZBCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-[2-(Benzenesulfonyl)-2,2-difluoroethyl]-5-methoxy-1,3-dimethylindol-2-one 在 sodium acetate 、 magnesium 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以89%的产率得到3-(2,2-difluoroethyl)-5-methoxy-1,3-dimethylindolin-2-one
  参考文献：
  名称：

  Pd（0）催化的活化烯烃的自由基芳基二氟甲基化。

  摘要：

  在温和的反应条件下已开发出Pd（0）催化的活化烯烃分子内芳基二氟甲基化反应。该反应为构建各种二氟甲基化的吲哚提供了一种新的方法。机理研究表明，由Pd（0）触发的二氟甲基自由基通过加成烯烃而引发了级联序列。

  DOI：

  10.1039/c3cc49315f

文献信息

• Synthesis of CF2H-containing oxindoles via photoredox-catalyzed radical difluoromethylation and cyclization of N-arylacrylamides
  作者：Mei Zhu、Qingqing You、Rongxia Li

  DOI：10.1016/j.jfluchem.2019.109391

  日期：2019.12

  difluoromethylation/cyclization of N-aryl acrylamides using difluoromethyl benzo[d]-thiazol-2-yl sulfone as the difluoromethylating reagent has been developed under mild conditions. This approach allows the synthesis a variety of useful CF2H-containing oxindoles in good to excellent yields. In addition, the photocatalytic difluoromethylation of methacryloyl benzamides and ortho-cyanoarylacrylamides via a similar

  已经在温和的条件下开发了使用二氟甲基苯并[d]-噻唑-2-基砜作为二氟甲基化试剂的N-芳基丙烯酰胺的光催化二氟甲基化/环化反应。这种方法可以合成各种有用的含CF 2 H的羟吲哚，收率好至极好。另外，还通过类似的自由基过程实现了甲基丙烯酰基苯甲酰胺和邻氰基芳基丙烯酰胺的光催化二氟甲基化。
• Visible-light induced radical aryldifluoromethylation of N-arylacrylamides by [bis(difluoroacetoxy)iodo]benzene
  作者：Kui Lu、Lingyu Lei、Qijun Wei、Ting Zhou、Xiaodong Jia、Quan Li、Xia Zhao

  DOI：10.1016/j.tetlet.2021.152864

  日期：2021.3

  Visible light-induced radical aryldifluoromethylation of N-arylacrylamides using [bis(difluoroacetoxy)iodo]benzene as a difluoromethylation reagent is reported for the first time. The inexpensive and readily accessible reagents and the mild reaction conditions render this method an alternative and practical strategy for the synthesis of difluoromethyl substituted oxindoles.

  首次报道了使用[双（二氟乙酰氧基）碘]苯作为二氟甲基化试剂的N-芳基丙烯酰胺的可见光诱导的自由基芳基二氟甲基化。廉价且易于获得的试剂和温和的反应条件使该方法成为合成二氟甲基取代的羟吲哚的替代和实用策略。
• Synthesis of Oxindoles through Silver-Catalyzed Trifluoromethylation-, Difluoromethylation- and Arylsulfonylation-Cyclization Reaction of<i>N</i>-Arylacrylamides
  作者：Jidan Liu、Shaobo Zhuang、Qingwen Gui、Xiang Chen、Zhiyong Yang、Ze Tan

  DOI：10.1002/ejoc.201400087

  日期：2014.5

  Efficient synthesis of trifluoromethyl and difluoromethyl-substituted oxindoles was achieved by reacting Langlois reagent or Baran reagent with N-arylacrylamides. However, the reaction of aryl sulfinic acid sodium salts with N-arylacrylamides did not give the desulfinative products, instead, aryl sulfonated products were produced.

  通过 Langlois 试剂或 Baran 试剂与 N-芳基丙烯酰胺反应，实现了三氟甲基和二氟甲基取代的羟吲哚的有效合成。然而，芳基亚磺酸钠盐与N-芳基丙烯酰胺的反应没有得到脱亚磺化产物，而是产生了芳基磺化产物。
• Synthesis of difluoromethylated 2-oxindoles and quinoline-2,4-diones <i>via</i> visible light-induced tandem radical cyclization of <i>N</i>-arylacrylamides
  作者：Huan Sun、Yue Jiang、Ying-Sha Yang、Yun-Yun Li、Lin Li、Wen-Xuan Wang、Tao Feng、Zheng-Hui Li、Ji-Kai Liu

  DOI：10.1039/c9ob01213c

  日期：——

  quinoline-2,4-diones under mild conditions via a proposed tandem radical addition/cyclization process along with good tolerance to various functional groups. In addition, preliminary experimental studies have revealed that water is a key factor in difluoromethylation and the reaction involves an oxidative quenching cycle of the photocatalyst.

  已经公开了可见光诱导的N-芳基丙烯酰胺的二氟甲基化，以二氟甲基2-吡啶基砜作为自由基前体提供二氟甲基化的2-氧吲哚和喹啉-2,4-二酮。该方法通过提议的串联自由基加成/环化过程以及对各种官能团的良好耐受性，可在温和条件下方便地获得各种2-氧吲哚和喹啉-2,4-二酮。另外，初步的实验研究表明，水是二氟甲基化的关键因素，反应涉及光催化剂的氧化淬灭循环。
• Visible-light photoredox-catalyzed radical aryldifluoromethylation of <i>N</i>-arylacrylamides with <i>S</i>-(difluoromethyl)sulfonium salt
  作者：Ya-Shi Zhao、Sheng-Jie Huang、Yuan-Qing Gu、Guo-Kai Liu

  DOI：10.1039/d3ob00488k

  日期：——

  A facile and highly efficient visible-light photoredox-catalyzed protocol for aryldifluoromethylation of acrylamides was developed using S-(difluoromethyl)sulfonium salt as the difluoromethyl source. With this method, pharmaceutically interesting CF2H-containing oxindoles were readily accessed from N-arylacrylamides, and this method featured mild reaction conditions, a broad scope of substrates, good

  使用S -（二氟甲基）硫盐作为二氟甲基源，开发了一种简便且高效的可见光光氧化还原催化协议，用于丙烯酰胺的芳基二氟甲基化。利用该方法，可以很容易地从N-芳基丙烯酰胺中获得具有药学意义的含CF 2 H的羟吲哚，该方法具有反应条件温和、底物范围广、官能团耐受性好、产率高等特点。对照实验表明，该方案通过二氟甲基化/环化级联过程进行。