1,3-dibenzyl-3-phenylindolin-2-one | 35524-70-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,3-dibenzyl-3-phenylindolin-2-one
• 英文别名: 1,3-Dibenzyl-3-phenyloxindol；1,3-dibenzyl-3-phenyl-1,3-dihydro-indol-2-one；1,3-Dibenzyl-3-phenylindol-2-one
• CAS: 35524-70-0
• 化学式: C₂₈H₂₃NO
• 分子量: 389.497
• InChiKey: OMGFJCXTLKPOIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 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-benzylamino-phenyl)-(phenyl)-methanone 在 silica gel 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 反应 21.0h， 生成 1,3-dibenzyl-3-phenylindolin-2-one
  参考文献：
  名称：

  硅胶介导的2-烷基氨基苯基prop-1-yn-3-ols的水胺化/ Semipinacol重排：由炔烃和1-（2-氨基苯基）酮合成2-Oxindoles

  摘要：

  Abstract2‐Alkylaminophenylprop‐1‐yn‐3‐ols, prepared from the lithium diisopropylamide (LDA)‐mediated 1,2‐addition of alkynes to 1‐(2‐aminophenyl) ketones, can be converted to 3,3‐disubstituted 2‐oxindoles by using silica gel in n‐hexane/ethyl acetate (20:1 v/v) as the reaction medium. The utility of the approach as a potential scale‐up strategy for the synthesis of 2‐oxindoles was exemplified by the large‐scale synthesis of one adduct in excellent yield. The synthetic applicability of this chemistry was also demonstrated by the recycling of the silica gel up to 8 times with no apparent loss of activity being observed for the same example.magnified image

  DOI：

  10.1002/adsc.201300911

文献信息

• Palladium-Catalyzed Chemoselective Activation of sp³ vs sp² C–H Bonds: Oxidative Coupling To Form Quaternary Centers
  作者：Gang Hong、Pradip D. Nahide、Uday Kumar Neelam、Peter Amadeo、Arjun Vijeta、John M. Curto、Charles E. Hendrick、Kelsey F. VanGelder、Marisa C. Kozlowski

  DOI：10.1021/acscatal.9b00091

  日期：2019.4.5

  activation of alkyl C–H bonds vs arene C–H bonds with Pd(OAc)2 has been found to be generalizable to a number of nucleophilic substrates, allowing the formation of a range of hindered quaternary centers. The substrates share a common mechanistic path wherein Pd(II) initiates an oxidative dimerization. The resultant dimer modifies the palladium catalyst to favor activation of alkyl C–H bonds, in contrast to

  发现Pd（OAc）2对烷基C–H键与芳烃C–H键的氧化活化作用可推广至许多亲核底物，从而形成一系列受阻的季中心。底物共有一条共同的机理，其中Pd（II）引发了氧化二聚作用。与通常通过协同的金属化-去质子化机理观察到的趋势相反，生成的二聚体修饰钯催化剂以促进烷基C-H键的活化。值得注意的是，对于受阻底物，插入发生在烷基芳烃的末端。发现了两种不同的氧化剂系统来完成该过程。已经鉴定出参数，该参数预测哪些底物在该反应中有生产力。
• Silica Gel-Mediated Hydroamination/Semipinacol Rearrangement of 2-Alkylaminophenylprop-1-yn-3-ols: Synthesis of 2-Oxindoles from Alkynes and 1-(2-Aminophenyl) Ketones
  作者：Dewi Susanti、Linda Li Ru Ng、Philip Wai Hong Chan

  DOI：10.1002/adsc.201300911

  日期：2014.2.10

  Abstract2‐Alkylaminophenylprop‐1‐yn‐3‐ols, prepared from the lithium diisopropylamide (LDA)‐mediated 1,2‐addition of alkynes to 1‐(2‐aminophenyl) ketones, can be converted to 3,3‐disubstituted 2‐oxindoles by using silica gel in n‐hexane/ethyl acetate (20:1 v/v) as the reaction medium. The utility of the approach as a potential scale‐up strategy for the synthesis of 2‐oxindoles was exemplified by the large‐scale synthesis of one adduct in excellent yield. The synthetic applicability of this chemistry was also demonstrated by the recycling of the silica gel up to 8 times with no apparent loss of activity being observed for the same example.magnified image