(1(R),2(S),8(S),8a(R))-1,2-O-Isopropylideneoctahydro-1,2,8-indolizidinetriol | 152005-86-2

• 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: (1(R),2(S),8(S),8a(R))-1,2-O-Isopropylideneoctahydro-1,2,8-indolizidinetriol
• CAS: 152005-86-2
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: HEVZREBCOASZGR-QEYWKRMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1(R),2(S),8(S),8a(R))-1,2-O-Isopropylideneoctahydro-1,2,8-indolizidinetriol 在 盐酸 作用下， 反应 0.5h， 以83%的产率得到(1R,2S,8S,8aR)-octahydro-1,2,8-indolizinetriol
  参考文献：
  名称：

  An acylnitroso cycloaddition approach to the synthesis of highly oxygenated indolizidine alkaloids

  摘要：

  A synthetic approach to the synthesis of highly oxygenated indolizidine alkaloids is described. A key feature of the approach is intramolecular [4 + 2] cycloaddition between an acylnitroso dienophile and a tethered diene moiety, followed by ring contraction of the 1,2-oxazine so formed to a pyrrolidine. The requisite intermediates were prepared in optically pure form froM L-glutamic acid.

  DOI：

  10.1021/jo00074a040
• 作为产物：
  描述：

  N-Succinimidyl 4(S)-<(tert-butyldiphenylsilyl)oxy>-5(E),7-octadienoate 在 disodium hydrogenphosphate 、 四氧化锇 、 N-甲基吲哚酮 、 sodium amalgam 、 tetrapropylammonium periodate 、 dimethyl sulfide borane 、 Dowex H⁽¹⁺⁾ resin 、 盐酸羟胺 、 四丁基氟化铵 、 potassium carbonate 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 57.5h， 生成 (1(R),2(S),8(S),8a(R))-1,2-O-Isopropylideneoctahydro-1,2,8-indolizidinetriol
  参考文献：
  名称：

  An acylnitroso cycloaddition approach to the synthesis of highly oxygenated indolizidine alkaloids

  摘要：

  A synthetic approach to the synthesis of highly oxygenated indolizidine alkaloids is described. A key feature of the approach is intramolecular [4 + 2] cycloaddition between an acylnitroso dienophile and a tethered diene moiety, followed by ring contraction of the 1,2-oxazine so formed to a pyrrolidine. The requisite intermediates were prepared in optically pure form froM L-glutamic acid.

  DOI：

  10.1021/jo00074a040

文献信息

• An acylnitroso cycloaddition approach to the synthesis of highly oxygenated indolizidine alkaloids
  作者：Gary E. Keck、Duane R. Romer

  DOI：10.1021/jo00074a040

  日期：1993.10

  A synthetic approach to the synthesis of highly oxygenated indolizidine alkaloids is described. A key feature of the approach is intramolecular [4 + 2] cycloaddition between an acylnitroso dienophile and a tethered diene moiety, followed by ring contraction of the 1,2-oxazine so formed to a pyrrolidine. The requisite intermediates were prepared in optically pure form froM L-glutamic acid.