3-(2-(4-fluorophenyl)-2-oxoethyl)-1,3-dimethylindolin-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-(4-fluorophenyl)-2-oxoethyl)-1,3-dimethylindolin-2-one
• 英文别名: 3-[2-(4-Fluorophenyl)-2-oxoethyl]-1,3-dimethylindol-2-one；3-[2-(4-fluorophenyl)-2-oxoethyl]-1,3-dimethylindol-2-one
• 化学式: C₁₈H₁₆FNO₂
• 分子量: 297.329
• InChiKey: YVDWEAOJSRCKSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4'-氟苯丙酮 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 三甲基氯硅烷 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 7.0h， 生成 3-(2-(4-fluorophenyl)-2-oxoethyl)-1,3-dimethylindolin-2-one
  参考文献：
  名称：

  肟酯的光催化CC键活化用于酰基自由基的产生和应用

  摘要：

  据报道，有一种通过选择性C–C键活化从肟酯生成酰基的统一策略。在可见光照射下，发生了从fac -Ir（ppy）3到相关肟的单电子转移，接着是快速的C-C键β片段产生芳基和脂族酰基基团，随后被各种Michael受体捕获。更有趣的是，单电子转移能够通过就地形成环丁烷的烯酮中间体与激发的fac -Ir（ppy）3的能量转移耦合。

  DOI：

  10.1021/acs.orglett.9b01338

文献信息

• Photocatalyst-free hypervalent iodine reagent catalyzed decarboxylative acylarylation of acrylamides with α-oxocarboxylic acids driven by visible-light irradiation
  作者：Wangqin Ji、Hui Tan、Min Wang、Pinhua Li、Lei Wang

  DOI：10.1039/c5cc08253f

  日期：——

  A hypervalent iodine (III) reagent catalyzed carbonylarylation of acrylamides with [small alpha]-oxocarboxylic acids driven by visible-light without photoredox catalyst has been developed. The reactions generate the corresponding products in good yields...

  已经开发了在不使用光氧化还原催化剂的情况下由可见光驱动的高价碘（III）试剂催化丙烯酰胺与α-氧代羧酸的羰基芳基化。该反应以高收率产生相应的产物。
• Metal-Free Generation of Acyl Radical via Photoinduced Single-Electron Transfer from Lewis Base to Acyl Chloride
  作者：Lei Bao、Zhi-Xiang Wang、Xiang-Yu Chen

  DOI：10.1021/acs.orglett.2c03339

  日期：2022.11.11

  We herein describe a simple approach for generating acyl radical from acyl chloride via photoinduced single-electron transfer. It has been demonstrated that the generated acyl radicals could react with various substrates, including isocyanides, methacrylamides, alkenes, alkynes, and enynes, to afford diverse heterocycles (>10 classes). Mechanistic analyses show that a photoactive charge transfer complex

  我们在此描述了一种通过光诱导单电子转移从酰氯产生酰基自由基的简单方法。已经证明，产生的酰基自由基可以与各种底物反应，包括异氰化物、甲基丙烯酰胺、烯烃、炔烃和烯炔，以提供多种杂环（> 10 类）。机理分析表明，酰氯和路易斯碱添加剂之间的光活性电荷转移络合物参与了酰基自由基的光生成。该研究举例说明了一种新的简单的羰基化合物光活化方法。
• Synthesis of Carbonyl-Containing Oxindoles via Ni-Catalyzed Reductive Aryl-Acylation and Aryl-Esterification of Alkenes
  作者：Zhengtian Ding、Wangqing Kong

  DOI：10.3390/molecules27185899

  日期：——

  active natural products and pharmaceutical molecules. Nickel-catalyzed reductive aryl-acylation of alkenes using aryl anhydrides or alkanoyl chlorides as acyl sources is developed, providing 3,3-disubstituted oxindoles bearing ketone functionality at the 3-position. Moreover, nickel-catalyzed reductive aryl-esterification of alkenes using chloroformate as ester sources is further developed, affording

  含羰基的羟吲哚是许多生物活性天然产物和药物分子中普遍存在的核心结构。开发了使用芳基酸酐或烷酰氯作为酰基源的镍催化的烯烃还原芳基酰化反应，提供在 3-位带有酮官能团的 3,3-二取代的羟吲哚。此外，进一步开发了使用氯甲酸酯作为酯源的镍催化的烯烃还原芳基酯化反应，得到在3位带有酯官能团的3,3-二取代的羟吲哚。该策略具有收率好、官能团相容性高等优点。
• UV Light-Mediated Difunctionalization of Alkenes through Aroyl Radical Addition/1,4-/1,2-Aryl Shift Cascade Reactions
  作者：Lewei Zheng、Hongli Huang、Chao Yang、Wujiong Xia

  DOI：10.1021/acs.orglett.5b00144

  日期：2015.2.20

  UV light-mediated difunctionalization of alkenes through an aroyl radical addition/1,4-/1,2-aryl shift has been described. The resulted aroyl radical from a photocleavage reaction added to acrylamide compounds followed by cyclization led to the formation of oxindoles, whereas the addition to cinnamic amides aroused a unique 1,4-aryl shift reaction. Furthermore, the difunctionalization of alkenes of prop-2-en-1-ols was also achieved through aroyl radical addition and a sequential 1,2-aryl shift cascade reaction.
• Silver-Catalyzed Decarboxylative Acylarylation of Acrylamides with α-Oxocarboxylic Acids in Aqueous Media
  作者：Hua Wang、Li-Na Guo、Xin-Hua Duan

  DOI：10.1002/adsc.201300468

  日期：2013.8.12

  AbstractA mild and efficient silver‐catalyzed acylarylation of activated alkenes with easily available α‐oxocarboxylic acids has been developed. The reactions provide a rapid access to a variety of functionalized oxindoles via a tandem decarboxylative radical cyclization strategy. This transformation proceeds well under mild reaction conditions and exhibits excellent functional group tolerance, affording the desired oxindoles in good to excellent yields.magnified image