3-(octan-2-yl)indolin-2-one

• 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-(octan-2-yl)indolin-2-one
• 英文别名: 3-Octan-2-yl-1,3-dihydroindol-2-one；3-octan-2-yl-1,3-dihydroindol-2-one
• 化学式: C₁₆H₂₃NO
• 分子量: 245.365
• InChiKey: KPVGLMPPNVYPNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-吲哚酮 、 仲辛醇 在 carbonyl(pentamethylcyclopentadienyl)cobalt diiodide 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以77%的产率得到3-(octan-2-yl)indolin-2-one
  参考文献：
  名称：

  C-Alkylation of Various Carbonucleophiles with Secondary Alcohols under Co^III-Catalysis

  摘要：

  Oxindoles have been successfully alpha-alkylated under Cp*Co-III catalysis by a vast array of secondary alcohols, including cyclic, acyclic, symmetrical, and unsymmetrical, to produce C-alkylated oxindoles. This protocol was also extended to the alpha-alkylation of N,N-dimethyl barbituric acid and benzyl cyanides. The kinetic profile and other preliminary mechanistic investigations suggest a first-order reaction rate in oxindoles and catalysts. A plausible catalytic cycle is proposed on the basis of the kinetic profile, of other preliminary mechanistic investigations, and of previous mechanistic studies on similar transformations, whereas density functional theory calculations provide insight into the nature of the active species.

  DOI：

  10.1021/acscatal.0c01728

文献信息

• C-Alkylation of Various Carbonucleophiles with Secondary Alcohols under Co^III-Catalysis
  作者：Priyanka Chakraborty、Nidhi Garg、Eric Manoury、Rinaldo Poli、Basker Sundararaju

  DOI：10.1021/acscatal.0c01728

  日期：2020.7.17

  Oxindoles have been successfully alpha-alkylated under Cp*Co-III catalysis by a vast array of secondary alcohols, including cyclic, acyclic, symmetrical, and unsymmetrical, to produce C-alkylated oxindoles. This protocol was also extended to the alpha-alkylation of N,N-dimethyl barbituric acid and benzyl cyanides. The kinetic profile and other preliminary mechanistic investigations suggest a first-order reaction rate in oxindoles and catalysts. A plausible catalytic cycle is proposed on the basis of the kinetic profile, of other preliminary mechanistic investigations, and of previous mechanistic studies on similar transformations, whereas density functional theory calculations provide insight into the nature of the active species.
• Manganese-Catalyzed C(α)-Alkylation of Oxindoles with Secondary Alcohols via Borrowing Hydrogen
  作者：Jagannath Rana、Palaniyappan Nagarasu、Murugan Subaramanian、Akash Mondal、Vedichi Madhu、Ekambaram Balaraman

  DOI：10.1021/acs.organomet.1c00009

  日期：2021.3.22