acetyl-1H-3-indolyle trifluoromethanesulfonate | 213881-67-5

• 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: acetyl-1H-3-indolyle trifluoromethanesulfonate
• 英文别名: (1-Acetylindol-3-yl) trifluoromethanesulfonate
• CAS: 213881-67-5
• 化学式: C₁₁H₈F₃NO₄S
• 分子量: 307.25
• InChiKey: IHLWUUBXLMMEBK-UHFFFAOYSA-N

物化性质

• 沸点：
  377.2±42.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  acetyl-1H-3-indolyle trifluoromethanesulfonate 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 diethyl 2-(3-acetyloxy-1H-indol-2-yl)propanedioate
  参考文献：
  名称：

  Reactions of 3-([(trifluoromethyl)sulfonyl]oxy)-1H-indole derivatives with diamines and carbon nucleophiles. Synthesis of 6H-indolo[2,3-b]quinoxaline derivatives

  摘要：

  Indolic triflate reacted with 1,2-diamines to afford pyrazino[2,3-b]indole or indolo[2,3-b] quinoxaline. Carbon nucleophiles such as malonate derivatives also reacted with indolic triflate in absence of palladium catalyst to afford 2-(3-oxo-2,3 -dihydro-1H-2-indolyliden) malonate derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00650-4
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 N-乙酰基-3-吲哚啉酮 在 lithium diisopropyl amide 作用下， 以77%的产率得到acetyl-1H-3-indolyle trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis and blue phosphorescent device performances of a new bipolar host material containing pyrazino[2,3-b]indole moiety

  摘要：

  新设计的双极主体材料（CzPhPz），由5H-吡嗪并[2,3-b]吲哚单元组成，已合成并展示出良好的电子传输性能，对于基于FIrpic的蓝色PHOLEDs具有高达2.83 eV的三重态能量。

  DOI：

  10.1039/c4ra10307f

文献信息

• Palladium-Catalyzed Reactions of Indolic Triflate with Allylic Alcohols
  作者：Béatrice Malapel-Andrieu、Jean-Yves Mérour

  DOI：10.1016/s0040-4039(97)10564-0

  日期：1998.1

  Reactions of 3-indolic triflate 2a with allylic alcohols in presence of palladium (II) acetate gave access to aldehydic compounds and in a more surprising way to C-2 substituted products and oxindole derivatives. © 1997 Elsevier Science Ltd. All rights reserved.

  在乙酸钯（II）的存在下3-吲哚三氟甲磺酸酯2a与烯丙基醇的反应得到醛化合物，并且以更令人惊奇的方式得到C -2取代的产物和羟吲哚衍生物。©1997 Elsevier ScienceLtd。保留所有权利。
• Synthesis and reactivity of substituted 3-([(Trifluoromethyl)sulfonyl]oxy)-1H-indole-2-carboxylate in palladium-catalyzed reactions
  作者：Béatrice Malapel-Andrieu、Jean-Yves Mérour

  DOI：10.1016/s0040-4020(98)00649-8

  日期：1998.9

  Palladium-catalysed Suzuki and Stille reactions of substituted 3-indolyltriflate afforded the corresponding 3-substituted indoles. By contrast, the Heck reaction of allyl alcohol with such triflates gave 2-allyloxy-3-oxoindole derivatives rather than the 3-substituted indole products as a result of a nucleophilic attack on an acyliminium intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Reactions of 3-([(trifluoromethyl)sulfonyl]oxy)-1H-indole derivatives with diamines and carbon nucleophiles. Synthesis of 6H-indolo[2,3-b]quinoxaline derivatives
  作者：Béatrice Malapel-Andrieu、Jean-Yves Mérour

  DOI：10.1016/s0040-4020(98)00650-4

  日期：1998.9

  Indolic triflate reacted with 1,2-diamines to afford pyrazino[2,3-b]indole or indolo[2,3-b] quinoxaline. Carbon nucleophiles such as malonate derivatives also reacted with indolic triflate in absence of palladium catalyst to afford 2-(3-oxo-2,3 -dihydro-1H-2-indolyliden) malonate derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis and blue phosphorescent device performances of a new bipolar host material containing pyrazino[2,3-b]indole moiety
  作者：Hong-Gu Jang、Sang Kyu Jeon、Jun Yeob Lee、Seok-Ho Hwang

  DOI：10.1039/c4ra10307f

  日期：——

  Newly designed bipolar host material (CzPhPz) consisting of 5H-pyrazino[2,3-b]indole unit was synthesized and exhibited good electron transport properties with a high triplet energy of 2.83 eV for FIrpic-based blue PHOLEDs.

  新设计的双极主体材料（CzPhPz），由5H-吡嗪并[2,3-b]吲哚单元组成，已合成并展示出良好的电子传输性能，对于基于FIrpic的蓝色PHOLEDs具有高达2.83 eV的三重态能量。