(2,5-dimethyl-1H-pyrrol-3-yl)(phenyl)methanone | 6982-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,5-dimethyl-1H-pyrrol-3-yl)(phenyl)methanone
• 英文别名: 3-benzoyl-2,5-dimethylpyrrole；(2,5-dimethyl-pyrrol-3-yl)-phenyl-methanone；(2,5-dimethyl-pyrrol-3-yl)-phenyl ketone；(2,5-Dimethyl-pyrrol-3-yl)-phenyl-keton；2,5-Dimethyl-3-benzoyl-pyrrol；3-Benzoyl-2,5-dimethyl-pyrrol；(2,5-dimethyl-1H-pyrrol-3-yl)-phenylmethanone
• CAS: 6982-75-8
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: FVLMJWSNDNKHNS-UHFFFAOYSA-N

物化性质

• 熔点：
  132 °C
• 沸点：
  340.3±30.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2,5-dimethyl-1H-pyrrol-3-yl)(phenyl)methanone 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 1,4-二氧六环 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (4-Bromo-2,5-dimethyl-1-pentyl-1H-pyrrol-3-yl)-phenyl-methanone
  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：

  2,5-二甲基吡咯 、 dimethoxy(phenyl)carbenium tetrafluoroborate 在 水 作用下， 生成 (2,5-dimethyl-1H-pyrrol-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Pindur, U.; Flo, C., Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1563 - 1568

  摘要：

  DOI：

文献信息

• Synthesis of Allenamides and Structurally Related Compounds by a Gold-Catalyzed Hydride Shift Process
  作者：Qing Zhao、Fabien Gagosz

  DOI：10.1002/adsc.201700615

  日期：2017.9.18

  A new procedure for the synthesis of allenamides and structurally related compounds is reported. Under gold catalysis, a series of ynamides possessing a benzyloxy group at the propargylic position were efficiently converted into the corresponding allenamides following a 1,5 hydride shift process. The scope of the reaction was shown to be extremely broad allowing the formation of γ‐mono or γ‐disubstituted

  报道了合成烯丙酰胺和结构相关化合物的新方法。在金催化下，在1，5氢化物转移过程之后，在炔丙基位置上具有苄氧基的一系列酰胺被有效地转化为相应的烯丙基酰胺。反应范围非常广泛，可以形成具有各种官能团的γ-单取代或γ-双取代的烯。值得注意的是，与以前报道的方法相比，不仅可以轻松，有效地获得N-烯基磺酰胺基，而且还可以轻松获得尿素，磷酰胺基和很少研究的邻苯二甲酰亚胺基，吡咯并，吲哚和咔唑衍生物。
• Oddo; Acuto, Gazzetta Chimica Italiana, 1935, vol. 65, p. 1029,1034
  作者：Oddo、Acuto

  DOI：——

  日期：——
• PINDUR, U.;FLO, C., J. HETEROCYCL. CHEM., 26,(1989) N, C. 1563-1568
  作者：PINDUR, U.、FLO, C.

  DOI：——

  日期：——