(5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-one | 152005-88-4

• 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,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-one
• CAS: 152005-88-4
• 化学式: C₂₇H₃₇NO₅Si
• 分子量: 483.68
• InChiKey: RMBCSUHTBAIAMS-HFOXQMJASA-N

物化性质

• 沸点：
  589.2±50.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-one 在 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 5.5h， 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：

  (3aS,9S,9aS,9bR)-9-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-hexahydro-1,3,5-trioxa-5a-aza-cyclopenta[a]naphthalen-6-one 在 disodium hydrogenphosphate 、 sodium amalgam 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-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