2-(azidomethyl)-1-benzyl-5-(4-methoxyphenyl)-1H-pyrrole | 1309589-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(azidomethyl)-1-benzyl-5-(4-methoxyphenyl)-1H-pyrrole
• 英文别名: 2-(Azidomethyl)-1-benzyl-5-(4-methoxyphenyl)pyrrole；2-(azidomethyl)-1-benzyl-5-(4-methoxyphenyl)pyrrole
• CAS: 1309589-25-0
• 化学式: C₁₉H₁₈N₄O
• 分子量: 318.378
• InChiKey: ZRGIWDWYNSFXRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(1-benzylaziridin-2-yl)-3-(4-methoxyphenyl)prop-2-yn-1-ol 在 四甲基乙二胺 、 silver(I) acetate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 2-(azidomethyl)-1-benzyl-5-(4-methoxyphenyl)-1H-pyrrole
  参考文献：
  名称：

  Synthesis of 1,2,5- and 1,2,3,5-substituted pyrroles from substituted aziridines via Ag(I)-catalyzed intramolecular cyclization

  摘要：

  An efficient synthesis of 1,2,5- and 1,2,3,5-substituted pyrroles has been achieved from the sequential reactions including a ring-opening of 1-(aziridin-2-yl)propargylic alcohols by various nucleophiles under mild condition followed by an intramolecular cyclization using Ag(I) catalyst. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.02.072

文献信息

• Atom Economical Multi-Substituted Pyrrole Synthesis from Aziridine
  作者：Lingamurthy Macha、Ranjith Jala、Sang-Yun Na、Hyun-Joon Ha

  DOI：10.3390/molecules27206869

  日期：——

  Multi-substituted pyrroles are synthesized from regiospecific aziridine ring-opening and subsequent intramolecular cyclization with a carbonyl group at the γ-position in the presence of Lewis acid or protic acid. This method is highly atom economical where all the atoms of the reactants are incorporated into the final product with the removal of water. This new protocol is applied to the synthesis of various

  在路易斯酸或质子酸存在下，多取代吡咯由区域特异性氮丙啶开环和随后在γ位与羰基进行分子内环化合成。这种方法是高度原子经济的，其中反应物的所有原子都结合到最终产品中，同时除去水。这一新协议适用于各种吡咯的合成，包括天然产物。
• Synthesis of 1,2,5- and 1,2,3,5-substituted pyrroles from substituted aziridines via Ag(I)-catalyzed intramolecular cyclization
  作者：Jun Hee Kim、Sang Bin Lee、Won Koo Lee、Doo-Ha Yoon、Hyun-Joon Ha

  DOI：10.1016/j.tet.2011.02.072

  日期：2011.5

  An efficient synthesis of 1,2,5- and 1,2,3,5-substituted pyrroles has been achieved from the sequential reactions including a ring-opening of 1-(aziridin-2-yl)propargylic alcohols by various nucleophiles under mild condition followed by an intramolecular cyclization using Ag(I) catalyst. (C) 2011 Published by Elsevier Ltd.