2-phenyl-4-(1-naphthoyl)-N-p-toluenesulfonylpyrrole | 914458-46-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-phenyl-4-(1-naphthoyl)-N-p-toluenesulfonylpyrrole
• 英文别名: 4-(1-naphthoyl)-2-phenyl-1-tosylpyrrole
• CAS: 914458-46-1
• 化学式: C₂₈H₂₁NO₃S
• 分子量: 451.546
• InChiKey: PQFQFHRXPQLJOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  56.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-(1-naphthoyl)-N-p-toluenesulfonylpyrrole 在 sodium hydride 作用下， 生成 1-naphthalenyl(1-pentyl-5-phenyl-1H-pyrrol-3-yl)methanone
  参考文献：
  名称：

  1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB1 and CB2 receptors

  摘要：

  Two series of 1-alkyl-2-aryl-4-(1-naphthoyl)pyrroles were synthesized and their affinities for the cannabinoid CB, and CB2 receptors were determined. In the 2-phenyl series (5) the N-alkyl group was varied from n-propyl to n-heptyl. A second series of 23 1-pentyl-2-aryl-4-(1-naphthoyl)-pyrroles (6) was also prepared. Several compounds in both series have CB, receptor affinities in the 6-30 nM range. The high affinities of these pyrrole derivatives relative to JWH-030 (1,R = C5H11) support the hypothesis that these pyrroles interact with the CB, receptor primarily by aromatic stacking. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.051
• 作为产物：
  描述：

  苯乙酮肟 在 三氯化铝 、 sodium hydride 作用下， 生成 2-phenyl-4-(1-naphthoyl)-N-p-toluenesulfonylpyrrole
  参考文献：
  名称：

  1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB1 and CB2 receptors

  摘要：

  Two series of 1-alkyl-2-aryl-4-(1-naphthoyl)pyrroles were synthesized and their affinities for the cannabinoid CB, and CB2 receptors were determined. In the 2-phenyl series (5) the N-alkyl group was varied from n-propyl to n-heptyl. A second series of 23 1-pentyl-2-aryl-4-(1-naphthoyl)-pyrroles (6) was also prepared. Several compounds in both series have CB, receptor affinities in the 6-30 nM range. The high affinities of these pyrrole derivatives relative to JWH-030 (1,R = C5H11) support the hypothesis that these pyrroles interact with the CB, receptor primarily by aromatic stacking. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.051

文献信息

• Acylation of N-p-toluenesulfonylpyrrole under Friedel–Crafts conditions: evidence for organoaluminum intermediates
  作者：John W. Huffman、Valerie J. Smith、Lea W. Padgett

  DOI：10.1016/j.tet.2007.12.043

  日期：2008.2

  The Friedel-Crafts acylation of N-p-toluenesulfonylpyrrole under Friedel-Crafts conditions has been reinvestigated. Evidence is presented in support of the hypothesis that when AlCl(3) is used as the Lewis acid, acylation proceeds via reaction of an organoaluminum intermediate with the acyl halide. This leads to the production of the 3-acyl derivative as the major product. With weaker Lewis acids (EtAlCl(2)

  重新研究了在 Friedel-Crafts 条件下 Np-甲苯磺酰基吡咯的 Friedel-Crafts 酰化。有证据支持以下假设：当 AlCl(3) 用作路易斯酸时，酰化通过有机铝中间体与酰卤的反应进行。这导致产生作为主要产物的 3-酰基衍生物。使用较弱的路易斯酸（EtAlCl(2)、Et(2)AlCl）或少于一当量的 AlCl(3) 时，2-酰基产物的相对量会增加。提出了机械合理化来解释这些数据。