1-benzyl-3-tert-butyl-2-methyl-1H-indole | 1013641-07-0

• 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-benzyl-3-tert-butyl-2-methyl-1H-indole
• 英文别名: 1-Benzyl-3-tert-butyl-2-methylindole；1-benzyl-3-tert-butyl-2-methylindole
• CAS: 1013641-07-0
• 化学式: C₂₀H₂₃N
• 分子量: 277.409
• InChiKey: VKXHDRKFWIUUKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N-benzyl-N-[2-(2,2-dimethyl-propionyl)-phenyl]-acetamide 在 titanium(III) chloride 、 锌 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.0h， 以68%的产率得到1-benzyl-3-tert-butyl-2-methyl-1H-indole
  参考文献：
  名称：

  Anionic N-Fries Rearrangement of N-Alkyl-2-iodo Anilides Induced by Iodine−Magnesium Exchange:  Application for Synthesis of Strained 1,2,3-Trisubstituted Indoles

  摘要：

  A superior, mild, high-yielding one-pot process for rapid access to oxo anilides has been developed that involves three cascade reactions: iodine-magnesium exchange, regiospecific ortho N-Fries rearrangement, and in situ trapping of the formed aniline anion. Coupled with McMurry cyclization, the two-step process allows ready synthesis of strained 1,2,3-trisubstituted indoles regioselectively.

  DOI：

  10.1021/ol7029905

文献信息

• Anionic N-Fries Rearrangement of N-Alkyl-2-iodo Anilides Induced by Iodine−Magnesium Exchange:  Application for Synthesis of Strained 1,2,3-Trisubstituted Indoles
  作者：Fei Ding、Yongda Zhang、Bo Qu、Guisheng Li、Vittorio Farina、Bruce Z. Lu、Chris H. Senanayake

  DOI：10.1021/ol7029905

  日期：2008.3.1

  A superior, mild, high-yielding one-pot process for rapid access to oxo anilides has been developed that involves three cascade reactions: iodine-magnesium exchange, regiospecific ortho N-Fries rearrangement, and in situ trapping of the formed aniline anion. Coupled with McMurry cyclization, the two-step process allows ready synthesis of strained 1,2,3-trisubstituted indoles regioselectively.