4-(4-fluorophenyl)-2-phenyl-1H-pyrrole | 1398057-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-(4-fluorophenyl)-2-phenyl-1H-pyrrole
• 英文别名: pyrrole
• CAS: 1398057-33-4
• 化学式: C₁₆H₁₂FN
• 分子量: 237.276
• InChiKey: MLXSLURREGGSDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.79
• 氢给体数：
  1.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-2-phenyl-1H-pyrrole 、 三氟化硼乙醚 在 sodium nitrite 、 三乙胺 作用下， 以 乙酸酐 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 2.17h， 以46%的产率得到
  参考文献：
  名称：

  Synthesis, structure and photophysical properties of NIR aza-BODIPYs with F/ N 3 / NH 2 groups at 1,7-positions

  摘要：

  With 4-fluorostyrene as the starting material, symmetric/asymmetric fluorine-containing aza-difluor-oboradiaza-s-indacenes (aza-BODIPYs) 3-6 at 1/7-position were successfully prepared. NaN3 undertook nucleophilic aromatic substitution via replacement of F atoms of 4 to form the N-3/NH2-containing aza-BODIPYs 9 and 10. The solid-state structure of aza-BODIPY 4 was confirmed by single crystal X-ray analysis, the F-Cph bond distance of which was found to be shorter than those of the reported fluoride. These aza-BODIPYs absorb and emit in the NIR region. Surprisingly, although the withdrawing group was introduced at 1/7 positions of 3-6, the effect of the fluorine atoms to the photophysical properties is trifling. However, 9 and 10 with N-3/NH2 groups resulted in a remarkable bathochromic shift. Aza-BODIPY 10 could be also used as a turn-on fluorescent probe for pH value. Moreover, the main photo physical data are well supported and explained by cLR-PCM(CHCI3)-M06-2X/6-311 + G(2d,p)/SOS-CIS(D) calculations. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.09.019
• 作为产物：
  描述：

  1-(4-氟苯基)-3-苯基-2-丙炔-1-酮 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 、 甲醇 为溶剂， 反应 12.0h， 生成 4-(4-fluorophenyl)-2-phenyl-1H-pyrrole
  参考文献：
  名称：

  碱促进的闭环羰基-丙二烯复分解反应合成2,4-二取代的吡咯

  摘要：

  N-烯丙基β-烯胺酮（由N-炔丙基β-烯胺酮原位产生）的碱促进的闭环羰基-烯丙烯复分解反应，得到2,4-二取代的吡咯，具有C（sp）-C（sp 3）债券。该无过渡金属步骤可产生1当量。乙酸作为唯一的副产物。初步的机理研究支持逐步[2 + 2]环加成/逆向[2 + 2]反应途径。

  DOI：

  10.1039/c8gc01675e

文献信息

• Reaction between 4-Nitro-1,3-diarylbutan-1-ones and Ammonium Acetate in the Presence of Morpholine and Sulfur: An Efficient Synthesis of 2,4-Diarylpyrroles
  作者：Mehdi Adib、Neda Ayashi、Fatemeh Heidari、Peiman Mirzaei

  DOI：10.1055/s-0035-1561852

  日期：——

  An efficient synthesis of 2,4-diarylpyrroles is described. Heating a mixture of a 4-nitro-1,3-diarylbutan-1-one and ammonium acetate in the presence of morpholine and sulfur afforded the corresponding 2,4-diarylpyrroles in excellent yields.

  描述了 2,4-二芳基吡咯的有效合成。在吗啉和硫的存在下加热 4-硝基-1,3-二芳基丁-1-酮和乙酸铵的混合物，以优异的产率得到相应的 2,4-二芳基吡咯。
• 2,4- vs 3,4-Disubsituted Pyrrole Synthesis Switched by Copper and Nickel Catalysts
  作者：Feng Chen、Tao Shen、Yuxin Cui、Ning Jiao

  DOI：10.1021/ol302270z

  日期：2012.9.21

  A novel and efficient copper or nickel catalyzed highly selective denitrogenative annulation of vinyl azides with aryl acetaldehydes has been developed. 2,4- and 3,4-diaryl substituted pyrroles, which are difficult to synthesize by the reported methods, can be highly regioselectively prepared by this protocol simply switched by the selection of the transition metal catalysts. Compared with the reported acidic or basic conditions for polysubstituted pyrrole synthesis, the present reaction conditions are mild, neutral, and very simple without any additives.