rac-ethyl (2R,3R)-3-(1H-pyrrol-1-yl)-3H-spiro[benzofuran-2,3'-pyrrolidine]-1'-carboxylate | 82831-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: rac-ethyl (2R,3R)-3-(1H-pyrrol-1-yl)-3H-spiro[benzofuran-2,3'-pyrrolidine]-1'-carboxylate
• CAS: 82831-04-7
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: GWSVLVAWUXRPDB-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  43.7
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  rac-ethyl (2R,3R)-3-(1H-pyrrol-1-yl)-3H-spiro[benzofuran-2,3'-pyrrolidine]-1'-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到cis-2,3-dihydro-1'-methyl-3-(1-pyrryl)spiro
  参考文献：
  名称：

  2,3-Dihydro-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine]s and 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,3'-pyrrolidine]s: novel antihypertensive agents

  摘要：

  A series of 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine]s (IV) and 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,3'-pyrrolidine]s (V) was synthesized and evaluated for cardiovascular activity. The majority of the compounds displayed good antihypertensive activity in the spontaneous hypertensive rat model at 50 mg/kg po. Compounds 5 (2,3-dihydro-1'-methyl-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine] ) and 12a (2,3-dihydro-1'-ethyl-3-(1-pyrryl)-spiro[benzofuran-2,4'-piperidine] ) were selected for a more detailed cardiovascular evaluation in the renal hypertensive rat and for standard cardiovascular challenges in anesthetized dogs and the sinoaortic-deafferented dog.

  DOI：

  10.1021/jm00364a027
• 作为产物：
  描述：

  1-[(2-氟苯基)甲基]吡咯 在 正丁基锂 、 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 25.0h， 生成 rac-ethyl (2R,3R)-3-(1H-pyrrol-1-yl)-3H-spiro[benzofuran-2,3'-pyrrolidine]-1'-carboxylate
  参考文献：
  名称：

  2,3-Dihydro-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine]s and 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,3'-pyrrolidine]s: novel antihypertensive agents

  摘要：

  A series of 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine]s (IV) and 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,3'-pyrrolidine]s (V) was synthesized and evaluated for cardiovascular activity. The majority of the compounds displayed good antihypertensive activity in the spontaneous hypertensive rat model at 50 mg/kg po. Compounds 5 (2,3-dihydro-1'-methyl-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine] ) and 12a (2,3-dihydro-1'-ethyl-3-(1-pyrryl)-spiro[benzofuran-2,4'-piperidine] ) were selected for a more detailed cardiovascular evaluation in the renal hypertensive rat and for standard cardiovascular challenges in anesthetized dogs and the sinoaortic-deafferented dog.

  DOI：

  10.1021/jm00364a027