3-sec-butyl-2(3H)-indolone

• 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-sec-butyl-2(3H)-indolone
• 英文别名: 3-sec-butylindolin-2-one；3-Butan-2-yl-1,3-dihydroindol-2-one；3-butan-2-yl-1,3-dihydroindol-2-one
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: DCRSWHHNGRFMII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  o'-(1-sec-butyl-2,2-difluorovinyl)-p-toluenesulfonanilide 在 三氟甲磺酸三甲基硅酯 、 palladium dichloride 、 水 、 碳酸氢钠 作用下， 以 1,1,1,3,3,3-hexafluoropropan-2-ol 为溶剂， 反应 24.0h， 以78%的产率得到3-sec-butyl-2(3H)-indolone
  参考文献：
  名称：

  Transition-metal-catalyzed Electrophilic Activation of 1,1-Difluoro-1-alkenes: Oxindole Synthesis via Intramolecular Amination

  摘要：

  在一定量的氯化钯（II）催化下，在正交位置带有磺酰胺基的β,β-二氟苯乙烯经三氟甲磺酸三甲基硅酯处理后，可以得到高产率的羰基吲哚。反应通过 5-内向-三重环化、水解和脱磺进行。这一系列反应使得二氟苯乙烯可以在一次反应中转化为游离的羰基吲哚。

  DOI：

  10.1246/cl.2010.248

文献信息

• Iron‐Catalyzed Borrowing Hydrogen <i>C</i> ‐Alkylation of Oxindoles with Alcohols
  作者：Mubarak B. Dambatta、Kurt Polidano、Alexander D. Northey、Jonathan M. J. Williams、Louis C. Morrill

  DOI：10.1002/cssc.201900799

  日期：——

  general and efficient iron‐catalyzed C‐alkylation of oxindoles has been developed. This borrowing hydrogen approach employing a (cyclopentadienone)iron carbonyl complex (2 mol %) exhibited a broad reaction scope, allowing benzylic and simple primary and secondary aliphatic alcohols to be employed as alkylating agents. A variety of oxindoles underwent selective mono‐C3‐alkylation in good‐to‐excellent

  已经开发了一种普遍有效的铁催化的吲哚的C烷基化反应。使用（环戊二烯酮）羰基铁络合物（2mol％）的这种借入氢方法表现出广泛的反应范围，允许将苄基和简单的伯和仲脂肪族醇用作烷基化剂。各种羟吲哚以良好的分离效率进行了选择性的单C 3-烷基化反应（28个实例，50-92％的产率，79％的平均产率）。
• 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
• Palla, Gerardo; Marchelli, Rosangela; Casnati, Giuseppe, Gazzetta Chimica Italiana, 1982, vol. 112, # 11/12, p. 535 - 536
  作者：Palla, Gerardo、Marchelli, Rosangela、Casnati, Giuseppe、Dossena, Arnaldo

  DOI：——

  日期：——
• Transition-metal-catalyzed Electrophilic Activation of 1,1-Difluoro-1-alkenes: Oxindole Synthesis via Intramolecular Amination
  作者：Hiroyuki Tanabe、Junji Ichikawa

  DOI：10.1246/cl.2010.248

  日期：2010.3.5

  In the presence of a catalytic amount of palladium(II) chloride, β,β-difluorostyrenes bearing a sulfonamido group at the ortho position were treated with trimethylsilyl trifluoromethanesulfonate to afford oxindoles in high yield. The reactions proceeded via 5-endo-trig cyclization, hydrolysis, and desulfonylation. This sequence allowed the transformation of difluorostyrenes into free oxindoles in a one-pot operation.

  在一定量的氯化钯（II）催化下，在正交位置带有磺酰胺基的β,β-二氟苯乙烯经三氟甲磺酸三甲基硅酯处理后，可以得到高产率的羰基吲哚。反应通过 5-内向-三重环化、水解和脱磺进行。这一系列反应使得二氟苯乙烯可以在一次反应中转化为游离的羰基吲哚。