3-(1-naphthoyl)-1-propylpyrrole | 162934-71-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1-naphthoyl)-1-propylpyrrole
• 英文别名: 1-Naphthyl(1-propyl-1H-pyrrol-3-yl)methanone；naphthalen-1-yl-(1-propylpyrrol-3-yl)methanone
• CAS: 162934-71-6
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: ANVCANCAZRKUGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(1-naphthoyl)-1-propylpyrrole 在 1,3-二溴-5,5-二甲基海因 作用下， 以 四氢呋喃 为溶剂， 生成 (5-Bromo-1-propyl-1H-pyrrol-3-yl)-naphthalen-1-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：

  (S)-naphthalen-1-yl(1-propyl-1H-pyrrol-3-yl)methanol 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以83%的产率得到3-(1-naphthoyl)-1-propylpyrrole
  参考文献：
  名称：

  通过胺催化的 Aldol/Paal-Knorr 反应序列的对映选择性直接合成 C3-羟基烷基化吡咯

  摘要：

  在吡咯的 C3 位创建具有手性的功能具有挑战性。已经开发了一种操作简单的有机催化方法，以在吡咯的 C3 位产生具有手性叔/季立体中心的功能。该过程通过丁二醛与各种受体羰基的胺催化直接羟醛反应进行，然后在同一罐中与伯胺发生 Paal-Knorr 反应。首次合成了一系列手性C3-羟基烷基化N-烷基/Ar/H-吡咯，具有良好的收率和高对映选择性。

  DOI：

  10.1021/acs.orglett.2c02922

文献信息

• 1-Alkyl-3-(1-naphthoyl)pyrroles: A new class of cannabinoid
  作者：Julia A.H. Lainton、John W. Huffman、Billy R. Martin、David R. Compton

  DOI：10.1016/0040-4039(95)00016-6

  日期：1995.2

  The design and synthesis of a series of 1-alkyl-3-(1-naphthoyl)pyrroles is described. Molecular modeling studies were employed to aid in the design of these compounds. During the course of the synthesis the Friedel-Crafts reactions of N-aryl sulfonyl pyrroles were reinvestigated. The title compounds (4) were subjected to pharmacological evaluation and the data obtained have enabled these pyrroles to

  描述了一系列1-烷基-3-（1-萘基）吡咯的设计和合成。分子模型研究被用来辅助这些化合物的设计。在合成过程中，对N-芳基磺酰基吡咯的Friedel-Crafts反应进行了重新研究。对标题化合物（4）进行药理评估，获得的数据已使这些吡咯能够被分类为大麻素。
• 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.
• Enantioselective Direct Synthesis of C3-Hydroxyalkylated Pyrrole via an Amine-Catalyzed Aldol/Paal–Knorr Reaction Sequence
  作者：Amol Prakash Pawar、Jyothi Yadav、Atul Jankiram Dolas、Yadav Kacharu Nagare、Eldhose Iype、Krishnan Rangan、Indresh Kumar

  DOI：10.1021/acs.orglett.2c02922

  日期：2022.10.21

  to generate functionality with a chiral tertiary/quaternary stereocenter at position C3 of pyrrole. The process proceeds through an amine-catalyzed direct aldol reaction of succinaldehyde with various acceptor carbonyls, followed by a Paal–Knorr reaction with a primary amine in the same pot. A series of chiral C3-hydroxyalkylated N-alkyl/Ar/H-pyrroles have been synthesized for the first time with good

  在吡咯的 C3 位创建具有手性的功能具有挑战性。已经开发了一种操作简单的有机催化方法，以在吡咯的 C3 位产生具有手性叔/季立体中心的功能。该过程通过丁二醛与各种受体羰基的胺催化直接羟醛反应进行，然后在同一罐中与伯胺发生 Paal-Knorr 反应。首次合成了一系列手性C3-羟基烷基化N-烷基/Ar/H-吡咯，具有良好的收率和高对映选择性。