(5S,8S,8aS)-5-<(tert-Butyldiphenylsilyl)oxy>pyrido<1,2-b><1,2>oxazin-8-one | 152005-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5S,8S,8aS)-5-<(tert-Butyldiphenylsilyl)oxy>pyrido<1,2-b><1,2>oxazin-8-one
• 英文别名: (4aS,5S)-5-[tert-butyl(diphenyl)silyl]oxy-4a,5,6,7-tetrahydro-2H-pyrido[1,2-b]oxazin-8-one
• CAS: 152005-79-3
• 化学式: C₂₄H₂₉NO₃Si
• 分子量: 407.585
• InChiKey: KFBBFWMKDPMTRH-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S,8S,8aS)-5-<(tert-Butyldiphenylsilyl)oxy>pyrido<1,2-b><1,2>oxazin-8-one 在 disodium hydrogenphosphate 、 四氧化锇 、 N-甲基吲哚酮 、 sodium amalgam 、 Dowex H⁽¹⁺⁾ resin 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 34.5h， 生成 (1(R),2(S),8(S),8a(R))-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
• 作为产物：
  描述：

  N-Succinimidyl 4(S)-<(tert-butyldiphenylsilyl)oxy>-5(E),7-octadienoate 在 tetrapropylammonium periodate 、 盐酸羟胺 、 二异丙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 7.0h， 生成 (5S,8S,8aS)-5-<(tert-Butyldiphenylsilyl)oxy>pyrido<1,2-b><1,2>oxazin-8-one
  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.