ethyl 1-(4-fluorophenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate | 1220831-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1-(4-fluorophenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate
• 英文别名: Ethyl 1-(4-fluorophenyl)-2-methyl-5-phenylpyrrole-3-carboxylate
• CAS: 1220831-39-9
• 化学式: C₂₀H₁₈FNO₂
• 分子量: 323.367
• InChiKey: KYKUJCZDAFDFHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-(4-fluorophenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(4-fluorophenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  Arylpiperazine-containing pyrrole 3-carboxamide derivatives targeting serotonin 5-HT2A, 5-HT2C, and the serotonin transporter as a potential antidepressant

  摘要：

  Arylpiperzine-containing pyrrole 3-carboxamide derivatives were synthesized and evaluated as novel antidepressant compounds. The various analogues were efficiently prepared and bio-assayed for binding to 5-HT2A, 5-HT2C receptor, and 5-HT transporter. Based on their in vitro and in vivo activities as well as selectivity over other neurotransmitter receptors and PK profiles, 33 and 34 were identified as lead compounds. Consequently, this pyrrole series of compounds appears to be promising enough to warrant further investigation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.093
• 作为产物：
  描述：

  2-甲基-5-苯基-1H-吡咯-3-羧酸乙酯 、 对氟碘苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 1-(4-fluorophenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Arylpiperazine-containing pyrrole 3-carboxamide derivatives targeting serotonin 5-HT2A, 5-HT2C, and the serotonin transporter as a potential antidepressant

  摘要：

  Arylpiperzine-containing pyrrole 3-carboxamide derivatives were synthesized and evaluated as novel antidepressant compounds. The various analogues were efficiently prepared and bio-assayed for binding to 5-HT2A, 5-HT2C receptor, and 5-HT transporter. Based on their in vitro and in vivo activities as well as selectivity over other neurotransmitter receptors and PK profiles, 33 and 34 were identified as lead compounds. Consequently, this pyrrole series of compounds appears to be promising enough to warrant further investigation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.093

文献信息

• Copper-mediated cross-coupling–cyclization–oxidation: a one-pot reaction to construct polysubstituted pyrroles
  作者：Pei Liu、Jin-ling Liu、Heng-shan Wang、Ying-ming Pan、Hong Liang、Zhen-Feng Chen

  DOI：10.1039/c3cc48728h

  日期：——

  A novel and efficient procedure for the synthesis of polysubstituted pyrroles has been developed in this work. The polysubsituted pyrroles were synthesized directly from terminal alkenes, amines and β-keto esters through cross-coupling–cyclization–oxidation in the presence of a catalytic amount of cuprous chloride. This method provides a one-pot synthesis route from terminal alkenes to polysubstituted pyrroles for the first time and opens a new area in cuprous catalysis.

  本文开发了一种新颖且高效的多取代吡咯合成方法。多取代吡咯是通过与终端烯烃、胺和β-酮酯在少量氯化亚铜催化剂存在下进行交叉耦合-环化-氧化反应直接合成的。这种方法首次提供了从终端烯烃到多取代吡咯的一锅合成路线，为亚铜催化开辟了新领域。