4-(P-溴苯基)-2-苯基吡咯 | 862201-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-(P-溴苯基)-2-苯基吡咯
• 英文名称: 4-(4-bromophenyl)-2-phenyl-1H-pyrrole
• CAS: 862201-35-2
• 化学式: C₁₆H₁₂BrN
• 分子量: 298.182
• InChiKey: LCICRFUIFZQWDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-(P-溴苯基)-2-苯基吡咯 在 盐酸 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 以83 %的产率得到
  参考文献：
  名称：

  2,4-Diarylpyrroles: synthesis, characterization and crystallographic insights

  摘要：

  Three 2,4-diarylpyrroles were synthesized starting from 4-nitrobutanones and the crystal structures of two derivatives were analysed. These are 4-(4-methoxyphenyl)-2-(thiophen-2-yl)-1H-pyrrole, C15H13NOS, and 3-(4-bromophenyl)-2-nitroso-5-phenyl-1H-pyrrole, C16H11BrN2O. Although pyrroles without substituents at the α-position with respect to the N atom are very air sensitive and tend to polymerize, we succeeded in growing an adequate crystal for X-ray diffraction analysis. Further derivatization using sodium nitrite afforded a nitrosyl pyrrole derivative, which crystallized in the triclinic space group P\overline{1} with Z = 6. Thus, herein we report the first crystal structure of a nitrosyl pyrrole. Interestingly, the co-operative hydrogen bonds in this NO-substituted pyrrole lead to a trimeric structure with bifurcated halogen bonds at the ends, forming a two-dimensional (2D) layer with interstitial voids having a radius of 5 Å, similar to some reported macrocyclic porphyrins.

  DOI：

  10.1107/s2053229624007277
• 作为产物：
  描述：

  4′-溴查耳酮 在 氢氧化钾 、 ammonium acetate 、 溶剂黄146 、 二乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.0h， 生成 4-(P-溴苯基)-2-苯基吡咯
  参考文献：
  名称：

  A Modular Synthesis of Unsymmetrical Tetraarylazadipyrromethenes

  摘要：

  A stepwise route to unsymmetrical tetraarylazadipyrromethenes by a condensation of 2,4-diaryl-5-nitroso-pyrroles with 2,4-diarylpyrroles is described. This modular building-block approach allows for the introduction of up to four different aryl substituents on the azadipyrromethene and is tolerant of a varied substituent set. An efficient synthesis of the 2,4-diarylpyrroles building blocks from 1,3-diaryl-4-nitro-butan-1-ones by nitro hydrolysis to a keto-aldehyde and subsequent ammonia condensation reaction has been achieved. The facile conversion of 2,4-diarylpyrroles into their alpha-nitroso analogues by their reaction with sodium nitrite generated the second building block required for the synthesis.

  DOI：

  10.1021/jo050696k

文献信息

• Base-promoted ring-closing carbonyl–allene metathesis for the synthesis of 2,4-disubstituted pyrroles
  作者：Guolin Cheng、Weiwei Lv、Lulu Xue

  DOI：10.1039/c8gc01675e

  日期：——

  A base-promoted ring-closing carbonyl–allene metathesis reaction of N-allenyl β-enaminones (generated in situ from N-propargyl β-enaminones) gives 2,4-disubstituted pyrroles with cleavage of the C(sp)–C(sp3) bond. This transition metal-free procedure generates 1 equiv. of acetic acid as the sole byproduct. A preliminary mechanistic study supports a stepwise [2 + 2] cycloaddition/retro [2 + 2] reaction

  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。
• 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。
• Synthesis of π-conjugated asymmetric aza-BODIPYs via nitrosobicyclopyrroles
  作者：Ryota Mori、Minenari Asakura、Yukinori Kobayashi、Hiromu Mashimo、Makoto Roppongi、Satoshi Ito

  DOI：10.1016/j.tetlet.2022.153759

  日期：2022.4

  π-Conjugated aza-BODIPYs with absorption in the near-infrared region have attracted attention, but there are few reports of their synthesis. We report the synthesis and absorption properties of π-conjugated asymmetric aza-BODIPYs by nitrosation and retro-Diels-Alder reaction of bicyclo[2.2.2]octadiene-fused bicyclopyrroles. We also synthesized aza-BODIPY fused with [2.3]naphtho and [2.3]anthra structures

  在近红外区域具有吸收的π-共轭氮杂-BODIPYs引起了人们的关注，但对其合成的报道很少。我们报告了通过双环[2.2.2]辛二烯稠合双环吡咯的亚硝化和逆-Diels-Alder 反应合成π-共轭不对称氮杂-BODIPYs 的性质和吸收性能。我们还首次通过该方法合成了融合[2.3]萘和[2.3]蒽结构的aza-BODIPY和π-共轭氮杂-O-螯合物BODIPY。
• A Modular Synthesis of Unsymmetrical Tetraarylazadipyrromethenes
  作者：Michael J. Hall、Shane O. McDonnell、John Killoran、Donal F. O'Shea

  DOI：10.1021/jo050696k

  日期：2005.7.1

  A stepwise route to unsymmetrical tetraarylazadipyrromethenes by a condensation of 2,4-diaryl-5-nitroso-pyrroles with 2,4-diarylpyrroles is described. This modular building-block approach allows for the introduction of up to four different aryl substituents on the azadipyrromethene and is tolerant of a varied substituent set. An efficient synthesis of the 2,4-diarylpyrroles building blocks from 1,3-diaryl-4-nitro-butan-1-ones by nitro hydrolysis to a keto-aldehyde and subsequent ammonia condensation reaction has been achieved. The facile conversion of 2,4-diarylpyrroles into their alpha-nitroso analogues by their reaction with sodium nitrite generated the second building block required for the synthesis.