(4aS,5aS,8aR,8bS)-7-Ethyl-3,4a-dimethyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡咯
• 英文名称: (4aS,5aS,8aR,8bS)-7-Ethyl-3,4a-dimethyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione
• 英文别名: (1S,2R,6S,8S)-4-ethyl-8,10-dimethyl-7-oxa-4,12-diazatricyclo[6.4.0.02,6]dodeca-9,11-diene-3,5-dione
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: PPUOSUXYEXGLRT-YVNDNENWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-二甲基吡啶N-氧化物 、 N-乙基马来酰亚胺 以 甲苯 为溶剂， 生成 (4aS,5aS,8aR,8bS)-7-Ethyl-3,4a-dimethyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione
  参考文献：
  名称：

  Synthesis and anthelmintic activity of 7-substituted 3,4a-dimethyl-4a,5a,8a,8b-tetrahydro-6H-pyrrolo[3′,4′:4,5]furo[3,2-b]pyridine-6,8(7H)-diones

  摘要：

  The racemic 7-substituted 3,4a-dimethyl-4a,5a,8a,8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-diones represent novel tricyclic compounds with strong in vivo efficacy against the parasitic nematode Haemonchus contortus Rudolphi in sheep. Here we report on the synthesis of tricyclic endo-2,3-dihydro[3,2-b]pyridine-type cycloadducts and describe the separation of the racemic 3,4a-dimethyl-7-ethyl-4a,5a,8a,8b-tetrahydro-6H-pyrrolo[3,4':4,5]furo[3,2]pyridine-6,8(7H)-dione into the enantiomers by HPLC. The absolute configuration of the most anthelmintically active (4aS,5aS,8aS,8bR)-enantiomer was determined by single crystal X-ray analysis using its stable (4aS,5aS,8aS,8bR)-enantiomer-CuCl2 (2:1)-complex. © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.089

文献信息

• Synthesis and anthelmintic activity of 7-substituted 3,4a-dimethyl-4a,5a,8a,8b-tetrahydro-6H-pyrrolo[3′,4′:4,5]furo[3,2-b]pyridine-6,8(7H)-diones
  作者：Peter Jeschke、Achim Harder、Winfried Etzel、Wolfgang Gau、Axel Göhrt、Jordi Benet-Buchholz、Gerhard Thielking

  DOI：10.1016/j.bmcl.2005.02.089

  日期：2005.5

  The racemic 7-substituted 3,4a-dimethyl-4a,5a,8a,8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-diones represent novel tricyclic compounds with strong in vivo efficacy against the parasitic nematode Haemonchus contortus Rudolphi in sheep. Here we report on the synthesis of tricyclic endo-2,3-dihydro[3,2-b]pyridine-type cycloadducts and describe the separation of the racemic 3,4a-dimethyl-7-ethyl-4a,5a,8a,8b-tetrahydro-6H-pyrrolo[3,4':4,5]furo[3,2]pyridine-6,8(7H)-dione into the enantiomers by HPLC. The absolute configuration of the most anthelmintically active (4aS,5aS,8aS,8bR)-enantiomer was determined by single crystal X-ray analysis using its stable (4aS,5aS,8aS,8bR)-enantiomer-CuCl2 (2:1)-complex. © 2005 Elsevier Ltd. All rights reserved.