3-benzyl-2-(4-methoxyphenyl)pyrrole | 1388830-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-benzyl-2-(4-methoxyphenyl)pyrrole
• 英文别名: 3-benzyl-2-(4-methoxyphenyl)-1H-pyrrole
• CAS: 1388830-41-8
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: YGMXYRSWWSFNJV-UHFFFAOYSA-N

物化性质

• 沸点：
  449.2±45.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-benzyl-2-(4-methoxyphenyl)pyrrole 在 哌啶 、 氢溴酸 、 溶剂黄146 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 zinc(II) bis[2,8-dibenzyl-1,9-bis(4-methoxyphenyl)dipyrrinato]
  参考文献：
  名称：

  Unusually Efficient Deformylative Synthesis of 1,2,8,9-Tetrasubstituted Dipyrrins from 4,5-Disubstituted Pyrrole-2-carbaldehydes

  摘要：

  Upon heating in a mixture of hydrobromic acid and acetic acid, 4-arylmethyl-5-(4-methoxyphenyl)pyrrole-2-carbaldehydes (9a-c) react to give 2,8-bis(arylmethyl)-1,9-bis(4-methoxyphenyl)dipyrrins (10a-c) in high yields, demonstrating the first example of an unusually efficient deformylative transformation of pyrrole-2-carbaldehyde to dipyrrin. Dipyrrins 10 show a clear color change from red to blue, when exposed to Bronsted acid. Structure of 10a.H+ was determined by X-ray crystallographic analysis. The absorption change of 10a in the presence of a metal ion was also studied.

  DOI：

  10.3987/com-14-s(k)10
• 作为产物：
  描述：

  5-(4-甲氧基苯基)-3,4-二氢-2H-吡咯 在 异-丁酸钾 、 四氯化钛 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 3-benzyl-2-(4-methoxyphenyl)pyrrole
  参考文献：
  名称：

  Unusually Efficient Deformylative Synthesis of 1,2,8,9-Tetrasubstituted Dipyrrins from 4,5-Disubstituted Pyrrole-2-carbaldehydes

  摘要：

  Upon heating in a mixture of hydrobromic acid and acetic acid, 4-arylmethyl-5-(4-methoxyphenyl)pyrrole-2-carbaldehydes (9a-c) react to give 2,8-bis(arylmethyl)-1,9-bis(4-methoxyphenyl)dipyrrins (10a-c) in high yields, demonstrating the first example of an unusually efficient deformylative transformation of pyrrole-2-carbaldehyde to dipyrrin. Dipyrrins 10 show a clear color change from red to blue, when exposed to Bronsted acid. Structure of 10a.H+ was determined by X-ray crystallographic analysis. The absorption change of 10a in the presence of a metal ion was also studied.

  DOI：

  10.3987/com-14-s(k)10

文献信息

• Copper-catalyzed three-component annulation toward pyrroles <i>via</i> the cleavage of two C–C bonds in 1,3-dicarbonyls
  作者：Gaochen Xu、Luchao Li、Binyan Xu、Zheng Fang、Jindian Duan、Kai Guo

  DOI：10.1039/d3cc02681g

  日期：——

  The first copper-catalyzed three-component annulation of α,β-unsaturated ketoximes, 1,3-dicarbonyls and paraformaldehyde has been documented. This novel strategy achieved the two C–C bond cleavage of 1,3-dicarbonyl compounds directly as a single-carbon synthon and provided a new and highly efficient method for the synthesis of 2,3-disubstituted pyrroles in moderate to good yields with broad functional

  首次铜催化的 α,β-不饱和酮肟、1,3-二羰基化合物和多聚甲醛的三组分成环反应已被记录。这种新颖的策略直接作为单碳合成子实现了1,3-二羰基化合物的两个C-C键断裂，并为2,3-二取代吡咯的合成提供了一种新的高效方法，收率中等至良好，具有广泛的应用前景。官能团兼容性。
• Facile Synthesis of 2,3-Disubstituted Pyrroles from 2-Substituted 1-Pyrrolines
  作者：Mitsunori Oda、Yurie Fujiwara、Taku Shoji、Takako Abe、Shigeyasu Kuroda

  DOI：10.3987/com-12-12457

  日期：——

  2-Substituted-1-pyrrolines react with various arylaldehyde acetals in the presence of a Lewis acid and base to give 2-substituted 3-arylmethylidene-1-pyrrolines, which are transformed to 2,3-disubstituted pyrroles by base-catalyzed double-bond isomerization.
• Unusually Efficient Deformylative Synthesis of 1,2,8,9-Tetrasubstituted Dipyrrins from 4,5-Disubstituted Pyrrole-2-carbaldehydes
  作者：Mitsunori Oda、Yurie Fujiwara、Yoshimitsu Kumai、Akira Ohta、Ryuta Miyatake

  DOI：10.3987/com-14-s(k)10

  日期：——

  Upon heating in a mixture of hydrobromic acid and acetic acid, 4-arylmethyl-5-(4-methoxyphenyl)pyrrole-2-carbaldehydes (9a-c) react to give 2,8-bis(arylmethyl)-1,9-bis(4-methoxyphenyl)dipyrrins (10a-c) in high yields, demonstrating the first example of an unusually efficient deformylative transformation of pyrrole-2-carbaldehyde to dipyrrin. Dipyrrins 10 show a clear color change from red to blue, when exposed to Bronsted acid. Structure of 10a.H+ was determined by X-ray crystallographic analysis. The absorption change of 10a in the presence of a metal ion was also studied.