tert-butyl 4-((1R,2S,3s,4R,5S)-3-((tert-butyldimethylsilyl)oxy)-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-yl)-3-oxobutanoate | 1349082-82-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: tert-butyl 4-((1R,2S,3s,4R,5S)-3-((tert-butyldimethylsilyl)oxy)-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-yl)-3-oxobutanoate
• CAS: 1349082-82-1
• 化学式: C₂₃H₄₀O₅Si
• 分子量: 424.653
• InChiKey: PGDDIZORUZYZDN-WDJGEFEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-((1R,2S,3s,4R,5S)-3-((tert-butyldimethylsilyl)oxy)-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-yl)-3-oxobutanoate 在 4-乙酰氨基苯磺酰叠氮 、 三乙胺 作用下， 以 乙腈 为溶剂， 以39%的产率得到tert-butyl 4-((1R,2S,3s,4R,5S)-3-((tert-butyldimethylsilyl)oxy)-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-yl)-2-diazo-3-oxobutanoate
  参考文献：
  名称：

  Desymmetrization of meso [3.2.1]oxabicyclic systems using metal-catalysed asymmetric intramolecular C–H insertion

  摘要：

  Diazoketone derivatives of meso 8-oxabicyclo[3.2.1]octen-3-ones were desymmetrized by an intramolecular C-H insertion mediated by chiral copper and dirhodium catalysts to generate oxatricyclic systems with up to 5 contiguous stereogenic centres and 50% ee. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.026
• 作为产物：
  描述：

  (1R,2S,4R,5S)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.59h， 生成 tert-butyl 4-((1R,2S,3s,4R,5S)-3-((tert-butyldimethylsilyl)oxy)-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-yl)-3-oxobutanoate
  参考文献：
  名称：

  Desymmetrization of meso [3.2.1]oxabicyclic systems using metal-catalysed asymmetric intramolecular C–H insertion

  摘要：

  Diazoketone derivatives of meso 8-oxabicyclo[3.2.1]octen-3-ones were desymmetrized by an intramolecular C-H insertion mediated by chiral copper and dirhodium catalysts to generate oxatricyclic systems with up to 5 contiguous stereogenic centres and 50% ee. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.026