5R-5-(1,2-O-cyclohexylidene-D-glycero-diitol-1-yl)-3-ethoxycarbonyl-4,5-dihydroisoxazole

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5R-5-(1,2-O-cyclohexylidene-D-glycero-diitol-1-yl)-3-ethoxycarbonyl-4,5-dihydroisoxazole
• 英文别名: ethyl (5R)-5-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]-4,5-dihydro-1,2-oxazole-3-carboxylate
• 化学式: C₁₄H₂₁NO₅
• 分子量: 283.324
• InChiKey: CRKBXUFHLHQYBH-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5R-5-(1,2-O-cyclohexylidene-D-glycero-diitol-1-yl)-3-ethoxycarbonyl-4,5-dihydroisoxazole 在 溶剂黄146 作用下， 反应 2.0h， 以80%的产率得到ethyl (5R)-5-[(1R)-1,2-dihydroxyethyl]-4,5-dihydro-1,2-oxazole-3-carboxylate
  参考文献：
  名称：

  Stereoselective cycloaddition of nitrile oxides to a dispiroketal-protected but-3-ene-1,2-diol

  摘要：

  The influence of a dispiroketal protecting group on the pi-facial selectivity of nitrile oxide cycloaddition to S-but-3-ene-1,2-diol has been investigated Ethoxycarbonylformonitrile oxide and benzonitrile oxide undergo regiospecific and diasteroeselective addition to alkene 7 to afford isoxazolines 11 and 12. The major adducts (11a and 11b) are formed with 44% and 50% d.e. respectively, and in each case have S-configuration at C-5, the new stereogenic centre.

  DOI：

  10.1016/0957-4166(95)00362-s
• 作为产物：
  描述：

  氯代肟基乙酸乙酯 在 3S-vinyl-1,4-dioxaspiro<5.0.4>decane 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 8.0h， 以52%的产率得到5S-5-(1,2-O-cyclohexylidene-D-glycero-diitol-1-yl)-3-ethoxycarbonyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  Stereoselective cycloaddition of nitrile oxides to a dispiroketal-protected but-3-ene-1,2-diol

  摘要：

  The influence of a dispiroketal protecting group on the pi-facial selectivity of nitrile oxide cycloaddition to S-but-3-ene-1,2-diol has been investigated Ethoxycarbonylformonitrile oxide and benzonitrile oxide undergo regiospecific and diasteroeselective addition to alkene 7 to afford isoxazolines 11 and 12. The major adducts (11a and 11b) are formed with 44% and 50% d.e. respectively, and in each case have S-configuration at C-5, the new stereogenic centre.

  DOI：

  10.1016/0957-4166(95)00362-s