4-(1-naphthoyl)-2-phenylpyrrole | 914458-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(1-naphthoyl)-2-phenylpyrrole
• 英文别名: naphthalen-1-yl(5-phenyl-1H-pyrrol-3-yl)methanone
• CAS: 914458-48-3
• 化学式: C₂₁H₁₅NO
• 分子量: 297.356
• InChiKey: UYGWRELGKKLPSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(1-naphthoyl)-2-phenylpyrrole 、 溴己烷 在 sodium hydride 作用下， 生成 1-己基-2-苯基-4-(1-萘甲酰)吡咯JWH-147
  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：

  2-phenyl-1-tosyl-1H-pyrrole 在 三氯化铝 作用下， 生成 4-(1-naphthoyl)-2-phenylpyrrole
  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

• [3+2] Anionic Cycloaddition of Isocyanides to Acyclic Enamines and Enaminones: A New, Simple, and Convenient Method for the Synthesis of 2,4-Disubstituted Pyrroles
  作者：Ilya V. Efimov、Maria D. Matveeva、Rafael Luque、Vasiliy A. Bakulev、Leonid G. Voskressensky

  DOI：10.1002/ejoc.201901776

  日期：2020.3.8

  Herein, a new route toward 2,4‐substituted pyrroles is presented. This is a new, simple, fast, and convenient method furnishing 2,4‐substituted pyrroles based on the formal cycloaddition reaction of isocyanides with acyclic enamines or enaminones under basic conditions.

  在此，提出了一种新的制备2,4-取代吡咯的途径。这是在异氰酸酯与无环烯胺或烯胺酮在碱性条件下正式环加成反应的基础上，提供2,4-取代吡咯的一种新的，简单，快速和方便的方法。