5-hydroxy-9-((S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yloxy)-2-oxabicyclo[3.3.1]non-6-en-8-one | 1159795-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 5-hydroxy-9-((S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yloxy)-2-oxabicyclo[3.3.1]non-6-en-8-one
• 英文别名: (1S,5R,9R)-5-hydroxy-9-[(2S)-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]oxy-2-oxabicyclo[3.3.1]non-6-en-8-one
• CAS: 1159795-93-3
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: WISLLKHQXTXGMT-ZGFBFQLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 (2S,4(1)R,7aS,10R,10aS)-10-bromo-2-methyltetrahydro-2H-benzofuro[4-b][1,4]dioxin-3,9(10H,10aH)-dione 在 三甲基铝 、 水 、 rochelle salt 作用下， 以 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 25.0h， 以55%的产率得到5-hydroxy-9-((S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yloxy)-2-oxabicyclo[3.3.1]non-6-en-8-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of All of the Known Chiral Cleroindicins (C−F): Clarification Among Optical Rotations and Assignments

  摘要：

  Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural product synthesis through the use sequential o-quinone methide chemistry and diastereoselective dearomatization. Natural cleroindicin F was shown to be nearly racemic, and an optically pure synthetic sample of cleroindicin F was found to racemize under slightly basic conditions. All other natural chiral cleroindicins are shown to be partially racemic.

  DOI：

  10.1021/jo900401k