(8aR)-5-hydroxy-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one | 342007-92-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (8aR)-5-hydroxy-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one
• CAS: 342007-92-5
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: ZOJLORPHZQIYAI-ULUSZKPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8aR)-5-hydroxy-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one 在 三乙基硅烷 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (-)-(8aR)-octahydroindolizine
  参考文献：
  名称：

  SmI2-mediated hetero-coupling reaction of lactams with aldehydes; synthesis of indolizidine alkaloids, (−)-δ-coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine

  摘要：

  Treatment of alicyclic and aromatic lactams with several aldehydes in the presence of samarium(II) diiodide was found to undergo a novel nitrogen-carbon (hetero) coupling reaction to generate N-alpha -hydroxyalkylated lactams in high yield. The chiral lactams with an aldehyde-side chain incorporating the L-pyroglutamic acid- or L-tartaric acid-derived skeleton also reacted intramolecularly under the same conditions to afford the corresponding bicyclic coupling products, which were further applied to the convenient syntheses of (-)-delta -coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00214-3
• 作为产物：
  描述：

  (S)-(+)-5-羟甲基-2-吡咯烷酮对甲苯磺酸酯 在 三氢化钐 、 四氧化锇 、 二碘甲烷 作用下， 以 四氢呋喃 为溶剂， 生成 (8aR)-5-hydroxy-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one
  参考文献：
  名称：

  SmI2-mediated hetero-coupling reaction of lactams with aldehydes; synthesis of indolizidine alkaloids, (−)-δ-coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine

  摘要：

  Treatment of alicyclic and aromatic lactams with several aldehydes in the presence of samarium(II) diiodide was found to undergo a novel nitrogen-carbon (hetero) coupling reaction to generate N-alpha -hydroxyalkylated lactams in high yield. The chiral lactams with an aldehyde-side chain incorporating the L-pyroglutamic acid- or L-tartaric acid-derived skeleton also reacted intramolecularly under the same conditions to afford the corresponding bicyclic coupling products, which were further applied to the convenient syntheses of (-)-delta -coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00214-3