(E)-ethyl 2-(1-methyl-2-oxoindolin-3-ylidene)acetate | 1416431-67-8

• 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: (E)-ethyl 2-(1-methyl-2-oxoindolin-3-ylidene)acetate
• 英文别名: (3E)-3-benzylidene-5-chloro-1-methylindol-2-one
• CAS: 1416431-67-8
• 化学式: C₁₆H₁₂ClNO
• 分子量: 269.73
• InChiKey: PTWIUAOIGXIQBZ-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-(1-methyl-2-oxoindolin-3-ylidene)acetate 、 苯 在 silver(I) acetate 、 palladium diacetate 、 三甲基乙酸 作用下， 反应 45.0h， 以56%的产率得到5-chloro-1-methyl-3-(diphenylmethylene)indolin-2-one
  参考文献：
  名称：

  Palladium-catalyzed oxidative arylation of trisubstituted olefin: an efficient synthesis of 3-(disubstituted)alkylidene-oxindoles

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2012.10.122
• 作为产物：
  描述：

  5-chloro-1-methylindolin-2-one 、 苯甲醇 在 heptahydrido bis(tricyclohexylphosphine)rheniume(VII) 、 lithium chloride 作用下， 以78.571%的产率得到
  参考文献：
  名称：

  Rhenium-Catalyzed Acceptorless Dehydrogenative Coupling via Dual Activation of Alcohols and Carbonyl Compounds

  摘要：

  The rhenium hetaphydride complex was found to be a versatile, homogeneous catalyst for dehydrogenative functionalization of alcohol. The dehydrogenative C-C coupling of alcohols and carbonyl compounds was carried out in the absence Of base and hydrogen acceptors to afford a series of alpha,beta-unsaturated carbonyl compounds. A possible dual activation pathway was proposed by mechanistic investigations.

  DOI：

  10.1021/cs400572q

文献信息

• Rhenium-Catalyzed Acceptorless Dehydrogenative Coupling via Dual Activation of Alcohols and Carbonyl Compounds
  作者：Hongming Jin、Jin Xie、Changduo Pan、Zhengbo Zhu、Yixiang Cheng、Chengjian Zhu

  DOI：10.1021/cs400572q

  日期：2013.10.4

  The rhenium hetaphydride complex was found to be a versatile, homogeneous catalyst for dehydrogenative functionalization of alcohol. The dehydrogenative C-C coupling of alcohols and carbonyl compounds was carried out in the absence Of base and hydrogen acceptors to afford a series of alpha,beta-unsaturated carbonyl compounds. A possible dual activation pathway was proposed by mechanistic investigations.
• 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.