diethyl 7-[5-(2-methyl-1,3-dioxolan-2-yl)hex-5-enylidene]-2,3-diazabicyclo[2.2.1]heptane-2,3-dicarboxylate | 187410-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl 7-[5-(2-methyl-1,3-dioxolan-2-yl)hex-5-enylidene]-2,3-diazabicyclo[2.2.1]heptane-2,3-dicarboxylate
• CAS: 187410-92-0
• 化学式: C₂₁H₃₂N₂O₆
• 分子量: 408.495
• InChiKey: HYKMXAZPOVSRKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  77.54
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl 7-[5-(2-methyl-1,3-dioxolan-2-yl)hex-5-enylidene]-2,3-diazabicyclo[2.2.1]heptane-2,3-dicarboxylate 在 氢氧化钾 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 、 potassium hexacyanoferrate(III) 作用下， 以 乙腈 为溶剂， 反应 23.92h， 生成 (4α,8α)-4-(2-methyl-1,3-dioxolan-2-yl)-3,4,5,6,7,8-hexahydro-2H-4,8-methanoazulen-1-one
  参考文献：
  名称：

  Diyl Trapping Reactions To Synthesize Taxol Analogs

  摘要：

  A new and efficient entry to the ABC-ring system common to taxol and related materials has been developed. Highlights include the use of a regioselective intramolecular diyl trapping reaction to synthesize tricyclic alkene 5, the creation and oxidative cleavage of the tetrasubstituted olefin found in ketal 20a,b to afford a highly functionalized eight-membered ring (21a), and cyclization of 22, thereby providing the tricyclic core.

  DOI：

  10.1021/jo970042e
• 作为产物：
  描述：

  diethyl 7-[5-(2-methyl-1,3-dioxolan-2-yl)hex-5-enylidene]-2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 在 potassium diazodicarboxylate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 diethyl 7-[5-(2-methyl-1,3-dioxolan-2-yl)hex-5-enylidene]-2,3-diazabicyclo[2.2.1]heptane-2,3-dicarboxylate
  参考文献：
  名称：

  Diyl Trapping Reactions To Synthesize Taxol Analogs

  摘要：

  A new and efficient entry to the ABC-ring system common to taxol and related materials has been developed. Highlights include the use of a regioselective intramolecular diyl trapping reaction to synthesize tricyclic alkene 5, the creation and oxidative cleavage of the tetrasubstituted olefin found in ketal 20a,b to afford a highly functionalized eight-membered ring (21a), and cyclization of 22, thereby providing the tricyclic core.

  DOI：

  10.1021/jo970042e