(5-溴-1-戊基-1H-吡咯-3-基)(萘-1-基)甲酮 | 914458-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (5-溴-1-戊基-1H-吡咯-3-基)(萘-1-基)甲酮
• 英文名称: 2-bromo-4-(1-naphthoyl)-1-pentylpyrrole
• 英文别名: (5-Bromo-1-pentyl-1H-pyrrol-3-yl)(naphthalen-1-yl)methanone；(5-bromo-1-pentylpyrrol-3-yl)-naphthalen-1-ylmethanone
• CAS: 914458-53-0
• 化学式: C₂₀H₂₀BrNO
• 分子量: 370.289
• InChiKey: VNMFYEMDLQQLSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (5-溴-1-戊基-1H-吡咯-3-基)(萘-1-基)甲酮 、 4-正丁基苯硼酸 在 四丁基溴化铵 palladium diacetate 、 potassium carbonate 、 三(邻甲基苯基)磷 作用下， 以 水 、 甲苯 为溶剂， 生成 JWH-371
  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：

  萘-1-基-(1-戊基吡咯-3-基)甲酮 在 1,3-二溴-5,5-二甲基海因 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(5-溴-1-戊基-1H-吡咯-3-基)(萘-1-基)甲酮
  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

• 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB1 and CB2 receptors
  作者：John W. Huffman、Lea W. Padgett、Matthew L. Isherwood、Jenny L. Wiley、Billy R. Martin

  DOI：10.1016/j.bmcl.2006.07.051

  日期：2006.10

  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.