1,3-bis(4-(trifluoromethyl)phenyl)isobenzofuran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-bis(4-(trifluoromethyl)phenyl)isobenzofuran
• 英文别名: 1,3-bis(p-trifluoromethylphenyl)isobenzofurane；1,3-Bis[4-(trifluoromethyl)phenyl]isobenzofuran；1,3-bis[4-(trifluoromethyl)phenyl]-2-benzofuran
• 化学式: C₂₂H₁₂F₆O
• 分子量: 406.327
• InChiKey: UPZHPETZUMDVSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,3-bis(4-(trifluoromethyl)phenyl)isobenzofuran 在 aluminum (III) chloride 、 sodium tetrahydroborate 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 20.0h， 生成 14,21-Bis[4-(trifluoromethyl)phenyl]-6,8-dithiapentacyclo[11.8.0.03,11.05,9.015,20]henicosa-1(21),2,4,9,11,13,15,17,19-nonaene-7-thione
  参考文献：
  名称：

  An electron-deficient tetrathiafulvalene-conjugated bistetracene

  摘要：

  An electron-deficient tetrathiafulvalene (TTF)-conjugated bistetracene 2 was synthesized as the counterpart of phenyl-substituted TTF-conjugated bistetracene 1, and was characterized in the molecular electronic structures based on the spectroscopic measurements. UV-vis absorption spectrum of 2 is slightly broader than that of 1 and fluorescence spectrum of 2 is red-shifted, reflecting the red-shifted absorption spectrum. The energy level of the highest occupied molecular orbital (HOMO) of 2 was directly determined by the atmospheric-photoelectron yield spectroscopy in powder to be -5.8 eV, which is remarkably lower than that of 1 (-5.2 eV). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.04.080
• 作为产物：
  描述：

  3-甲氧基苯酞 、 4-三氟甲基苯基溴化镁 以 四氢呋喃 为溶剂， 以47%的产率得到1,3-bis(4-(trifluoromethyl)phenyl)isobenzofuran
  参考文献：
  名称：

  A Single-Step Synthesis of Symmetrical 1,3-Diarylisobenzofurans

  摘要：

  本文描述了一种便捷的单步合成多种对称取代的1,3-二芳基异苯并呋喃的方法，该方法以易于获得的3-甲氧基-3H-异苯并呋喃-1-酮（1a）和两倍量的芳基格氏试剂为原料。目标产物以中等至较高的分离收率获得。未经纯化的异苯并呋喃亦可通过马来酰亚胺捕获，近乎定量地得到纯净的Diels-Alder加成物。

  DOI：

  10.1055/s-2006-948179

文献信息

• A Single-Step Synthesis of Symmetrical 1,3-Diarylisobenzofurans
  作者：Jacques Einhorn、Farah Benderradji、Malek Nechab、Cathy Einhorn

  DOI：10.1055/s-2006-948179

  日期：2006.8

  A convenient single-step synthesis of various symmetrically substituted 1,3-diarylisobenzofurans from readily available 3-methoxy-3H-isobenzofuran-1-one (1a) and two equivalents of aryl Grignard reagents is described. The title compounds are obtained in medium to high isolated yields. Crude isobenzofuran has also been trapped by maleimide, furnishing pure Diels-Alder adduct almost quantitatively.

  本文描述了一种便捷的单步合成多种对称取代的1,3-二芳基异苯并呋喃的方法，该方法以易于获得的3-甲氧基-3H-异苯并呋喃-1-酮（1a）和两倍量的芳基格氏试剂为原料。目标产物以中等至较高的分离收率获得。未经纯化的异苯并呋喃亦可通过马来酰亚胺捕获，近乎定量地得到纯净的Diels-Alder加成物。
• A Stable Heptacene Derivative Substituted With Electron-Deficient Trifluoromethylphenyl and Triisopropylsilylethynyl Groups
  作者：Hemi Qu、Chunyan Chi

  DOI：10.1021/ol101158y

  日期：2010.8.6

  A heptacene derivative 1 substituted with four electron-deficient trifluoromethylphenyl and two triisopropylsilylethynyl (TIPSE) groups was prepared by a new synthetic strategy. Photo-oxidative resistance studies showed that this newly developed heptacene compound persisted 47 h in solution under ambient light and air conditions, and it represents the most stable heptacene derivative reported to date

  通过新的合成策略制备了被四个缺电子的三氟甲基苯基和两个三异丙基甲硅烷基乙炔基（TIPSE）取代的庚并衍生物1。光氧化抗性研究表明，这种新开发的庚并苯化合物在环境光和空气条件下在溶液中可持续47 h，它代表了迄今为止报道的最稳定的庚并苯衍生物。
• An electron-deficient tetrathiafulvalene-conjugated bistetracene
  作者：Masataka Yamashita、Hironobu Hayashi、Naoki Aratani、Hiroko Yamada

  DOI：10.1016/j.tetlet.2015.04.080

  日期：2015.6

  An electron-deficient tetrathiafulvalene (TTF)-conjugated bistetracene 2 was synthesized as the counterpart of phenyl-substituted TTF-conjugated bistetracene 1, and was characterized in the molecular electronic structures based on the spectroscopic measurements. UV-vis absorption spectrum of 2 is slightly broader than that of 1 and fluorescence spectrum of 2 is red-shifted, reflecting the red-shifted absorption spectrum. The energy level of the highest occupied molecular orbital (HOMO) of 2 was directly determined by the atmospheric-photoelectron yield spectroscopy in powder to be -5.8 eV, which is remarkably lower than that of 1 (-5.2 eV). (C) 2015 Elsevier Ltd. All rights reserved.