7-fluoro-3a-methyl-3,4-dihydro-2H-pyrrolo[1,2-a]indol-1-one | 1282060-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-fluoro-3a-methyl-3,4-dihydro-2H-pyrrolo[1,2-a]indol-1-one
• CAS: 1282060-58-5
• 化学式: C₁₂H₁₂FNO
• 分子量: 205.232
• InChiKey: UIJZHZBMCTWVRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-Fluoro-2-(2-methylprop-2-enyl)aniline 在 吡啶 、 allylchloro[1,3-bis(2,6-di-iso-propylphenyl)imidazol-2-ylidene]palladium (II) 、 potassium tert-butylate 、 氧气 、 三甲基丙酮酸 作用下， 以 2-甲基-2-丁醇 、 二氯甲烷 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 7-fluoro-3a-methyl-3,4-dihydro-2H-pyrrolo[1,2-a]indol-1-one
  参考文献：
  名称：

  Palladium(II)-Catalyzed Intramolecular Tandem Aminoalkylation via Divergent C(sp³)–H Functionalization

  摘要：

  We have developed a Pd(II)-catalyzed oxidative tandem aminoalkylation via divergent C(sp(3))-H functionalization, affording three- and five-membered-ring fused indolines in good yields under two optimized conditions, respectively. The mechanism studies have indicated that the benzylic C-H cleavage involved in the former transformation is the rate-determining step, while the cleavage of amide α-C-H in the latter is not. This is the first example of a Pd-catalyzed tandem reaction involving C(sp(3))-H activation without the employment of prefunctionalized reagents (e.g., halogenated and boron reagents) and directing groups, representing a green and economic protocol for the construction of N-containing heterocycles.

  DOI：

  10.1021/ja5102739

文献信息

• Pd(II)-Catalyzed Intramolecular Amidoarylation of Alkenes with Molecular Oxygen as Sole Oxidant
  作者：Kai-Tai Yip、Dan Yang

  DOI：10.1021/ol2006083

  日期：2011.4.15

  Stereoselective palladium-catalyzed synthesis of structurally versatile indoline derivatives, using molecular oxygen as the sole oxidant, is described. New C-N and C-C bonds form across an alkene in an intramolecular manner. The C-N bond-forming step proceeds via a syn-amidopalladation pathway. The moderate kinetic isotope effects (intramolecular KIE = 3.56) suggest that electrophilic aromatic substitution occurs in the arylation step.