N-acetyl-2-methyl-1H-benzo[f]indole | 1451075-09-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-acetyl-2-methyl-1H-benzo[f]indole
• 英文别名: 1-(2-methyl-1H-benzo[f ]indol-1-yl)ethanone；1-(2-Methylbenzo[f]indol-1-yl)ethanone；1-(2-methylbenzo[f]indol-1-yl)ethanone
• CAS: 1451075-09-4
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: ZAVKXTVWEUZJGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  烯丙基甲基碳酸酯 、 N-乙醯萘胺 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 24.0h， 以68%的产率得到N-acetyl-2-methyl-1H-benzo[f]indole
  参考文献：
  名称：

  Rh(III)-Catalyzed Tandem C–H Allylation and Oxidative Cyclization of Anilides: A New Entry to Indoles

  摘要：

  Rh-III-catalyzed tandem C-H allylation and oxidative cyclization of anilides with allyl carbonates in the presence of a slight excess of AgSbF6 salt and Cu(OAc)(2) as oxidant affords easy, economical access to important bioactive 2-methylindoles. The new reaction supports a wide range of functional groups on the anilide substrate. A possible mechanism is proposed as a basis for its rational further development.

  DOI：

  10.1021/ol402125t

文献信息

• Synthesis and C2-functionalization of indoles with allylic acetates under rhodium catalysis
  作者：Mirim Kim、Jihye Park、Satyasheel Sharma、Sangil Han、Sang Hoon Han、Jong Hwan Kwak、Young Hoon Jung、In Su Kim

  DOI：10.1039/c3ob41828f

  日期：——

  Tandem rhodium-catalyzed oxidative allylation and annulation of acetanilides with allyl acetate to afford the corresponding indoles are described. In addition, the site-selective C2 allylation, crotylation and prenylation of indoles using allylic acetates under rhodium catalysis are reported.

  介绍了铑催化的乙酰苯胺与乙酸烯丙酯的氧化烯丙基化和环化反应，从而得到相应的吲哚。此外，还报道了在铑催化下使用烯丙基乙酸酯进行吲哚的位点选择性 C2 烯丙基化、巴豆基化和预炔基化。
• Rh(III)-Catalyzed Tandem C–H Allylation and Oxidative Cyclization of Anilides: A New Entry to Indoles
  作者：Ana Cajaraville、Susana López、Jesús A. Varela、Carlos Saá

  DOI：10.1021/ol402125t

  日期：2013.9.6

  Rh-III-catalyzed tandem C-H allylation and oxidative cyclization of anilides with allyl carbonates in the presence of a slight excess of AgSbF6 salt and Cu(OAc)(2) as oxidant affords easy, economical access to important bioactive 2-methylindoles. The new reaction supports a wide range of functional groups on the anilide substrate. A possible mechanism is proposed as a basis for its rational further development.