2,5-dimethyl-1-pentyl-1H-pyrrole | 20293-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,5-dimethyl-1-pentyl-1H-pyrrole
• 英文别名: 2,5-dimethyl-1-pentyl-pyrrole；2,5-Dimethyl-1-pentyl-pyrrol；2,5-dimethyl-1-pentylpyrrole
• CAS: 20293-41-8
• 化学式: C₁₁H₁₉N
• mdl: MFCD12187077
• 分子量: 165.279
• InChiKey: USQGYTGFFUAGPL-UHFFFAOYSA-N

物化性质

• 沸点：
  225-227 °C
• 密度：
  0.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.636
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  γ-丁内酯 、 2,5-dimethyl-1-pentyl-1H-pyrrole 在 PPA 作用下， 反应 24.0h， 以12%的产率得到1-(2,5-Dimethyl-1-pentyl-1H-pyrrol-3-yl)-4-hydroxy-butan-1-one
  参考文献：
  名称：

  Synthesis and structure–activity relationships of a series of pyrrole cannabinoid receptor agonists

  摘要：

  We designed and synthesized a series of pyrrole derivatives with the aim of investigating the structure-activity relationship (SAR) for the binding of non-classical agonists to CB1 and CB2 cannabinoid receptors. Superposition of two pyrrole-containing cannabinoid agonists, JWH-007 and JWH-161, allowed us to identify positions 1, 3 and 4 of the pyrrole nucleus as amenable to additional investigation. We prepared the 1-alkyl-2,5-dimethyl-3,4-substituted pyrroles 10a-e, 11a-d, 17, 21, 25 and the tetrahydroindole 15, and evaluated their ability to bind to and activate cannabinoid receptors. Noteworthy in this set of compounds are the 4-bromopyrrole 11a, which has an affinity for CB1 and CB2 receptors comparable to that of well-characterized heterocyclic cannabimimetics such as Win-55,212-2; the amide 25, which, although possessing a moderate affinity for cannabinoid receptors, demonstrates that the 3-naphthoyl group, commonly present in indole and pyrrole cannabimimetics, can be substituted by alternative moieties; and compounds 10d, 11d, showing CB1 partial agonist properties. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00413-9
• 作为产物：
  描述：

  1-氨基戊烷 、 2,5-己二酮 生成 2,5-dimethyl-1-pentyl-1H-pyrrole
  参考文献：
  名称：

  Karrer; Smirnoff, Helvetica Chimica Acta, 1922, vol. 5, p. 851

  摘要：

  DOI：

文献信息

• Acceptorless Dehydrogenative Coupling Using Ammonia: Direct Synthesis of N-Heteroaromatics from Diols Catalyzed by Ruthenium
  作者：Prosenjit Daw、Yehoshoa Ben-David、David Milstein

  DOI：10.1021/jacs.8b08385

  日期：2018.9.26

  The synthesis of N-heteroaromatic compounds via an acceptorless dehydrogenative coupling process involving direct use of ammonia as the nitrogen source was explored. We report the synthesis of pyrazine derivatives from 1,2-diols and the synthesis of N-substituted pyrroles by a multicomponent dehydrogenative coupling of 1,4-diols and primary alcohols with ammonia. The acridine-based Ru-pincer complex

  探索了通过直接使用氨作为氮源的无受体脱氢偶联过程合成 N-杂芳族化合物。我们报告了从 1,2-二醇合成吡嗪衍生物以及通过 1,4-二醇和伯醇与氨的多组分脱氢偶联合成 N-取代吡咯。吖啶基 Ru-钳形配合物 1 是这些转化的有效催化剂，其中吖啶主链转化为阴离子脱芳构化 PNP-钳形配体框架。
• New 2,5-Dimethylpyrrole Derivatives
  作者：W. S. Bishop

  DOI：10.1021/ja01228a502

  日期：1945.12
• US4551540A
  申请人：——

  公开号：US4551540A

  公开（公告）日：1985-11-05
• US4511725A
  申请人：——

  公开号：US4511725A

  公开（公告）日：1985-04-16
• US4551539A
  申请人：——

  公开号：US4551539A

  公开（公告）日：1985-11-05