1-Benzyloxy-4-(1-methyl-1H-indol-3-yl)-butan-2-ol | 596105-54-3

• 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: 1-Benzyloxy-4-(1-methyl-1H-indol-3-yl)-butan-2-ol
• CAS: 596105-54-3
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: OSOQKHMOGQKXCB-UHFFFAOYSA-N

物化性质

• 沸点：
  505.4±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  34.39
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-Benzyloxy-4-(1-methyl-1H-indol-3-yl)-butan-2-ol 在 palladium diacetate 烟酸乙酯 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 potassium tert-butylate 、 氧气 、 溶剂黄146 作用下， 以 2-甲基-2-丁醇 、 二氯甲烷 、 甲苯 为溶剂， 23.0~80.0 ℃ 、101.33 kPa 条件下， 反应 30.25h， 生成 3-Benzyloxymethyl-4-methyl-3-vinyl-1,2,3,4-tetrahydro-cyclopenta[b]indole
  参考文献：
  名称：

  Catalytic C−H Bond Functionalization with Palladium(II):  Aerobic Oxidative Annulations of Indoles

  摘要：

  A palladium-catalyzed aerobic oxidative annulation of indoles is described. We have demonstrated that a variety of factors influence these cyclizations, and in particular the electronic nature of the pyridine ligand is crucial. It is also remarkable that these oxidative cyclizations can proceed in good yield despite background oxidative decomposition pathways, testament to the facile nature with which molecular oxygen can serve as the direct oxidant for Pd(0). We have also shown that the mechanism most likely involves initial indole palladation (formal C-H bond activation) followed by migratory insertion and beta-hydrogen elimination.

  DOI：

  10.1021/ja035054y
• 作为产物：
  描述：

  3-(1-methylindol-3-yl)propionaldehyde 在 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.67h， 生成 1-Benzyloxy-4-(1-methyl-1H-indol-3-yl)-butan-2-ol
  参考文献：
  名称：

  Catalytic C−H Bond Functionalization with Palladium(II):  Aerobic Oxidative Annulations of Indoles

  摘要：

  A palladium-catalyzed aerobic oxidative annulation of indoles is described. We have demonstrated that a variety of factors influence these cyclizations, and in particular the electronic nature of the pyridine ligand is crucial. It is also remarkable that these oxidative cyclizations can proceed in good yield despite background oxidative decomposition pathways, testament to the facile nature with which molecular oxygen can serve as the direct oxidant for Pd(0). We have also shown that the mechanism most likely involves initial indole palladation (formal C-H bond activation) followed by migratory insertion and beta-hydrogen elimination.

  DOI：

  10.1021/ja035054y