N-acetyl-2-methyl-5-(trifluoromethyl)-1H-indole | 1451075-08-3

• 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: N-acetyl-2-methyl-5-(trifluoromethyl)-1H-indole
• 英文别名: 1-(2-methyl-5-(trifluoromethyl)-1H-indol-1-yl)ethanone；1-(5-trifluoromethyl-2-methyl-1H-indol-1-yl)ethanone；1-[2-Methyl-5-(trifluoromethyl)indol-1-yl]ethanone；1-[2-methyl-5-(trifluoromethyl)indol-1-yl]ethanone
• CAS: 1451075-08-3
• 化学式: C₁₂H₁₀F₃NO
• 分子量: 241.213
• InChiKey: GEGXUYLLKUXTHY-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：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  烯丙基甲基碳酸酯 、 N1-[4-(三氟甲基0苯基]乙酰氨 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 、 silver carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以65%的产率得到N-acetyl-2-methyl-5-(trifluoromethyl)-1H-indole
  参考文献：
  名称：

  Synthesis of indoles through Rh(III)-catalyzed C–H cross-coupling with allyl carbonates

  摘要：

  A practical Rh-catalyzed reaction was developed to achieve 2-alkyl-substituted indole synthesis. The reaction can tolerate a variety of synthetically important functional groups. The indole products can also be transformed into other important skeletons. Two bioactive compounds, that is indomethacin and pravadoline were prepared using the new method. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.11.065

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.
• Synthesis of indoles through Rh(III)-catalyzed C–H cross-coupling with allyl carbonates
  作者：Tian-Jun Gong、Wan-Min Cheng、Wei Su、Bin Xiao、Yao Fu

  DOI：10.1016/j.tetlet.2013.11.065

  日期：2014.3

  A practical Rh-catalyzed reaction was developed to achieve 2-alkyl-substituted indole synthesis. The reaction can tolerate a variety of synthetically important functional groups. The indole products can also be transformed into other important skeletons. Two bioactive compounds, that is indomethacin and pravadoline were prepared using the new method. (C) 2014 Published by Elsevier Ltd.