1-(4-(benzyloxy)phenyl)-1H-pyrrole | 3260-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4-(benzyloxy)phenyl)-1H-pyrrole
• 英文别名: 1-(4-Phenylmethoxyphenyl)pyrrole；1-(4-phenylmethoxyphenyl)pyrrole
• CAS: 3260-14-8
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: HSENRJFPWIHWGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.058
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苄氧基-4-碘苯 、 L-羟基脯氨酸 在 copper(l) iodide 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以89%的产率得到1-(4-(benzyloxy)phenyl)-1H-pyrrole
  参考文献：
  名称：

  New strategy for the synthesis of N-aryl pyrroles: Cu-catalyzed C–N cross-coupling reaction of trans-4-hydroxy-l-proline with aryl halides

  摘要：

  trans-4-Hydroxy-L-proline is used for the first time as an effective nucleophilic coupling partner with aryl halides mediated by copper iodide with Cs(2)CO(3) as the base and DMSO as the solvent. Utilizing this protocol cross-coupling of trans-4-hydroxy-L-proline with a wide variety of substituted aryl halides to produce N-aryl pyrroles in moderate to good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.016

文献信息

• An elegant protocol for the synthesis of N-substituted pyrroles through C–N cross coupling/aromatization process using CuFe2O4 nanoparticles as catalyst under ligand-free conditions
  作者：G. Satish、K. Harsha Vardhan Reddy、K. Ramesh、B.S.P. Anil Kumar、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2014.01.075

  日期：2014.4

  A simple and efficient, ligand-free C-N cross-coupling of aryl halides/benzyl bromides with trans-4-hydroxy-L-proline has been developed to produce aromatized N-substituted pyrroles, using a catalytic amount of magnetically separable and recyclable CuFe2O4 nanoparticles, in the presence of Cs2CO3 in DMSO at 100 degrees C. (C) 2014 Elsevier Ltd. All rights reserved.
• New strategy for the synthesis of N-aryl pyrroles: Cu-catalyzed C–N cross-coupling reaction of trans-4-hydroxy-l-proline with aryl halides
  作者：V. Prakash Reddy、A. Vijay Kumar、K. Rama Rao

  DOI：10.1016/j.tetlet.2010.12.016

  日期：2011.2

  trans-4-Hydroxy-L-proline is used for the first time as an effective nucleophilic coupling partner with aryl halides mediated by copper iodide with Cs(2)CO(3) as the base and DMSO as the solvent. Utilizing this protocol cross-coupling of trans-4-hydroxy-L-proline with a wide variety of substituted aryl halides to produce N-aryl pyrroles in moderate to good yields. (C) 2010 Elsevier Ltd. All rights reserved.