tert-butyl 2-(trifluoromethylsulfonyloxy)-1H-indole-1-carboxylate | 1373936-42-5

• 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: tert-butyl 2-(trifluoromethylsulfonyloxy)-1H-indole-1-carboxylate
• 英文别名: 2-[(Trifluoromethyl)sulfonyloxy]-1H-indole-1-carboxylic acid tert-butyl ester；tert-butyl 2-(trifluoromethylsulfonyloxy)indole-1-carboxylate
• CAS: 1373936-42-5
• 化学式: C₁₄H₁₄F₃NO₅S
• 分子量: 365.33
• InChiKey: IDFZNUYMRIWWMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(trifluoromethylsulfonyloxy)-1H-indole-1-carboxylate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以97%的产率得到tert-butyl 2-hydroxy-3-(trifluoromethylsulfonyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Regioselective Synthesis of Heteroaryl Triflones by LDA (Lithium Diisopropylamide)-Mediated Anionic Thia-Fries Rearrangement

  摘要：

  Novel heteroaryl triflones including oxindole, pyrazolone, pyridine, and quinoline derivatives have been regioselectively synthesized by LDA-mediated thia-Fries rearrangement for the first time. These reactions are also the first examples of the application of anionic thia-Fries rearrangement in heteroaromatic compounds.

  DOI：

  10.1021/ol300842d
• 作为产物：
  描述：

  2-吲哚酮 在 2,4,6-三叔丁基吡啶 、 sodium carbonate 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 tert-butyl 2-(trifluoromethylsulfonyloxy)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Regioselective Synthesis of Heteroaryl Triflones by LDA (Lithium Diisopropylamide)-Mediated Anionic Thia-Fries Rearrangement

  摘要：

  Novel heteroaryl triflones including oxindole, pyrazolone, pyridine, and quinoline derivatives have been regioselectively synthesized by LDA-mediated thia-Fries rearrangement for the first time. These reactions are also the first examples of the application of anionic thia-Fries rearrangement in heteroaromatic compounds.

  DOI：

  10.1021/ol300842d

文献信息

• Development of a Suzuki Cross-Coupling Reaction between 2-Azidoarylboronic Pinacolate Esters and Vinyl Triflates To Enable the Synthesis of [2,3]-Fused Indole Heterocycles
  作者：Navendu Jana、Quyen Nguyen、Tom G. Driver

  DOI：10.1021/jo500252e

  日期：2014.3.21

  The scope and limitations of a Suzuki reaction between 2-azidoarylboronic acid pinacolate esters and vinyl triflates are reported. This cross-coupling reaction enables the regioselective synthesis of indoles after a subsequent RhII2-catalyzed sp2-C–H bond amination reaction.

  报道了 2-叠氮基硼酸频哪酸酯和乙烯基三氟甲磺酸酯之间的 Suzuki 反应的范围和局限性。这种交叉偶联反应能够在随后的 Rh II 2催化的 sp 2 -C-H 键胺化反应后区域选择性地合成吲哚。
• Regioselective Synthesis of Heteroaryl Triflones by LDA (Lithium Diisopropylamide)-Mediated Anionic Thia-Fries Rearrangement
  作者：Xiu-Hua Xu、Xin Wang、Guo-kai Liu、Etsuko Tokunaga、Norio Shibata

  DOI：10.1021/ol300842d

  日期：2012.5.18

  Novel heteroaryl triflones including oxindole, pyrazolone, pyridine, and quinoline derivatives have been regioselectively synthesized by LDA-mediated thia-Fries rearrangement for the first time. These reactions are also the first examples of the application of anionic thia-Fries rearrangement in heteroaromatic compounds.