(1(S),2(R),8(S),8a(S))-8-(tert-Butyldiphenylsiloxy)-1,2-(isopropylidenedioxy)octahydro-5-indolizidinone

• 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(S),2(R),8(S),8a(S))-8-(tert-Butyldiphenylsiloxy)-1,2-(isopropylidenedioxy)octahydro-5-indolizidinone
• 英文别名: (3aR,9S,9aR,9bS)-9-[tert-butyl(diphenyl)silyl]oxy-2,2-dimethyl-4,7,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-a]indolizin-6-one
• 化学式: C₂₇H₃₅NO₄Si
• 分子量: 465.665
• InChiKey: ZDEAWFQGRGHJDV-TVYALGDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1(S),2(R),8(S),8a(S))-8-(tert-Butyldiphenylsiloxy)-1,2-(isopropylidenedioxy)octahydro-5-indolizidinone 在 盐酸 、 dimethyl sulfide borane 、 四丁基氟化铵 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 (1S,2R,8R,8aS)-octahydro-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
• 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 、 Dowex H⁽¹⁺⁾ resin 、 盐酸羟胺 、 potassium carbonate 、 三乙胺 、 二异丙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 41.5h， 生成 (1(S),2(R),8(S),8a(S))-8-(tert-Butyldiphenylsiloxy)-1,2-(isopropylidenedioxy)octahydro-5-indolizidinone
  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.