2-(trifluoromethyl)indene | 134391-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2-(trifluoromethyl)indene
• 英文别名: 2-(trifluoromethyl)-1H-indene
• CAS: 134391-55-2
• 化学式: C₁₀H₇F₃
• 分子量: 184.161
• InChiKey: AILSPTOIEMSZAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三氟碘甲烷 、 茚 在 吡啶 作用下， 反应 336.0h， 以37%的产率得到2-(trifluoromethyl)indene
  参考文献：
  名称：

  Synthesis of perfluoroalkylated indenes

  摘要：

  A series of perfluoroalkylated indenes has been synthesized using four different synthetic pathways. 1-(Pentafluoroethyl)indene and 2-(pentafluoroethyl)indene were prepared by the addition of (pentafluoroethyl)lithium to the appropriate ketones and subsequent dehydration. 2-(Trifluoromethyl)indene was synthesized through the photoinduced addition of trifluoromethyl iodide to indene, followed by dehydroiodination. 1-(Trifluoromethyl)indene was prepared by the addition of (trifluoromethyl)trimethylsilane to 1-indanone followed by deprotection and dehydration and by the sigmatropic cyclization of the appropriate phenylvinyl carbocation. This latter approach was also used to synthesize 1,3-bis(trifluoromethyl)indene and 1,2,3-tris(trifluoromethyl)indene.

  DOI：

  10.1021/jo00017a029

文献信息

• Free-Radical Bromotrifluoromethylation of Olefin via Single-Electron Oxidation of NaSO₂CF₃ by NaBrO₃
  作者：Zhong-Quan Liu、Dong Liu

  DOI：10.1021/acs.joc.6b02812

  日期：2017.2.3

  A free-radical bromotrifluoromethylation of olefin by using NaSO2CF3 and NaBrO3 has been achieved. Sodium bromate acts not only as a single-electron oxidant but also as a bromine source. A radical-clock experiment and electron-spin-resonance detection support a radical process.

  通过使用NaSO 2 CF 3和NaBrO 3已经实现了烯烃的自由基溴三氟甲基化。溴酸钠不仅充当单电子氧化剂，而且还充当溴源。自由基钟实验和电子自旋共振检测支持自由基过程。
• A general one-pot synthesis for elusive 2-substituted indenes: does bis[2-(tert-butyl)indenyl]zirconium(<scp>iv</scp>) dichloride/MAO polymerise ethene?
  作者：Andreas C. Möller、Richard Blom、Richard H. Heyn、Ole Swang、Jürgen Kopf、Tanja Seraidaris

  DOI：10.1039/b516130d

  日期：——

  indenes, 2-trifluoroindene and 2-tert-butylindene are poorly or incompletely described in the open literature. We herein describe an efficient one-pot synthesis of these compounds as a variation of the Perkin reaction which allows us to refute an earlier claim that bis(2-tert-butylindenyl)zirconium(IV) dichloride (2a) will not polymerise ethene. In fact, 2a/MAO polymerises ethene to extremely high molecular

  在2-取代基之中 表示，2-三氟茚和 2-叔丁基茚在公开文献中很少或不完整地描述。我们在本文中描述了这些化合物的有效一锅合成方法，作为珀金反应的一种变化形式，它使我们可以驳斥一个先前的主张，即二氯化双（2-叔丁基茚基）锆（IV）（2a）不会聚合乙烯。实际上，2a / MAO聚合乙烯到极高的分子量。关于聚合机理的大量DFT计算表明，由于活性位的空间拥塞，β-氢化物转移对其他主要的链终止反应产生了空前的抑制作用。
• Synthesis of perfluoroalkylated indenes
  作者：Paul G. Gassman、Julia A. Ray、Paul G. Wenthold、John W. Mickelson

  DOI：10.1021/jo00017a029

  日期：1991.8

  A series of perfluoroalkylated indenes has been synthesized using four different synthetic pathways. 1-(Pentafluoroethyl)indene and 2-(pentafluoroethyl)indene were prepared by the addition of (pentafluoroethyl)lithium to the appropriate ketones and subsequent dehydration. 2-(Trifluoromethyl)indene was synthesized through the photoinduced addition of trifluoromethyl iodide to indene, followed by dehydroiodination. 1-(Trifluoromethyl)indene was prepared by the addition of (trifluoromethyl)trimethylsilane to 1-indanone followed by deprotection and dehydration and by the sigmatropic cyclization of the appropriate phenylvinyl carbocation. This latter approach was also used to synthesize 1,3-bis(trifluoromethyl)indene and 1,2,3-tris(trifluoromethyl)indene.