5-chloro-1-methyl-3-(diphenylmethylene)indolin-2-one | 1039395-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-chloro-1-methyl-3-(diphenylmethylene)indolin-2-one
• 英文别名: 5-chloro-3-(diphenylmethylene)-1-methylindolin-2-one；1-methyl-5-chloro-3-(diphenylmethylene)indolin-2-one；3-Benzhydrylidene-5-chloro-1-methylindol-2-one
• CAS: 1039395-90-8
• 化学式: C₂₂H₁₆ClNO
• 分子量: 345.828
• InChiKey: OAODGTKWRIOEBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  N-(4-chlorophenyl)-N-methyl-3-phenylpropiolamide 、 碘苯二乙酸 在 palladium diacetate 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 7.0h， 以81%的产率得到5-chloro-1-methyl-3-(diphenylmethylene)indolin-2-one
  参考文献：
  名称：

  Palladium-Catalyzed C−H Functionalization of N-Arylpropiolamides with Aryliodonium Salts: Selective Synthesis of 3-(1-Arylmethylene)oxindoles

  摘要：

  A selective and efficient method for the synthesis of 3-(1-arylmethylene)oxindoles by palladium-catalyzed C-H functionalization of anilides with aryliodonium salts has been developed. In the presence of Pd(OAc)(2) and Et3N, a variety of anilides underwent the reaction with aryliodonium salts to afford the corresponding 3-(1-arylmethylene)oxindoles in moderate to good yields. It is noteworthy that the reaction can be conducted providing moderate yields even without bases. The mechanism of the reaction was also discussed.

  DOI：

  10.1021/jo8008808

文献信息

• Palladium Nanoparticle-Catalyzed Stereoselective Domino Synthesis of All-Carbon Tetrasubstituted Olefin Containing Oxindoles via Carbopalladation/C–H Activation
  作者：Naziya Parveen、Govindasamy Sekar

  DOI：10.1021/acs.joc.0c00915

  日期：2020.8.21

  catalyzed single-step, stereoselective domino synthesis of symmetrically and unsymmetrically all-carbon tetrasubstituted olefin containing oxindoles from readily accessible anilides has been developed. The Pd-BNP catalyst showed a wide range of functional group tolerance that enabled building a library of heteroaromatics. This reusable Pd catalyst reflected its utility in the synthesis of biologically important

  已经开发了由萘甲酸稳定的钯纳米粒子（Pd-BNP）的一步合成的立体选择性多米诺骨牌合成方法，该方法由易于获得的苯胺类化合物合成对称和不对称的含氧吲哚的全碳四取代烯烃。Pd-BNP催化剂显示出广泛的官能团耐受性，从而能够建立杂芳烃库。这种可重复使用的Pd催化剂反映了其在合成生物学上重要的AMP活化的蛋白激酶（不含任何金属Pd污染）的实用性。纳米催化剂易于回收并重复使用五次，而粒度或催化活性没有任何明显的损失。
• Palladium-catalyzed oxidative arylation of trisubstituted olefin: an efficient synthesis of 3-(disubstituted)alkylidene-oxindoles
  作者：Hyun Ju Lee、Ko Hoon Kim、Se Hee Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2012.10.122

  日期：2013.1

  A palladium-catalyzed oxidative arylation of 3-(monosubstituted)alkylidene-oxindoles with arenes afforded 3-(disubstituted)alkylidene-oxindoles in good to moderate yields. (C) 2012 Elsevier Ltd. All rights reserved.
• Selective Synthesis of 3-Aryl Quinolin-2(1<i>H</i>)-ones and 3-(1-Arylmethylene)oxindoles Involving a 2-Fold Arene C−H Activation Process
  作者：Dong-Jun Tang、Bo-Xiao Tang、Jin-Heng Li

  DOI：10.1021/jo901314t

  日期：2009.9.4

  A novel and selective palladium-catalyzed C-H activation protocol has been developed for the synthesis of 3-aryl quinolin-2(1H)-ones and 3-(1-arylmethylene)oxindoles with use of PivOH as the switch. In the presence of Pd(OAc)(2), AgOAc, and PivOH, a variety or N-methyl anilides reacted with arenes to afford the corresponding 3-aryl quinolin-2(l H)-ones in moderate yields, whereas the selectivity was shifted toward 3-(1-arylmethylene)oxindoles in the absence of PivOH.