(1S,3R,5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octan-2-one | 1560848-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S,3R,5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octan-2-one
• 英文别名: (1S,3R,5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octan-2-one
• CAS: 1560848-65-8
• 化学式: C₂₁H₃₁NO₄Si
• 分子量: 389.567
• InChiKey: KBIBNKZZYHBMOR-SSWGBVJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  51.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octan-2-one 在 迭氮酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 10.33h， 生成 N-[(1R,5R,6S)-5-[(tert-butyldimethylsilyl)oxy]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]acetamide
  参考文献：
  名称：

  Use of Aziridines for the Stereocontrolled Synthesis of (−)-LL-C10037α, (+)-MT35214, and (+)-4-epi-MT35214

  摘要：

  Strategies for the synthesis of the title compounds have been developed using a diastereoselective aziridination reaction of 4-O-substituted cyclohexenones. Aziridination using a chiral amine permitted resolution of a 4-hydroxycyclohexane derivative, and this resulted in the synthesis of both enantiomers of the title compound. Alternatively, the chiral 4-hydroxycyclohexenone starting material was derived from quinic acid. In both cases stereoselective epoxidation and opening of the aziridine ring with hydrazoic acid afforded the 2-azidocyclohexenone, which was transformed to the 2-acetamido group present in the natural product.

  DOI：

  10.1021/jo402535j
• 作为产物：
  描述：

  (1S,5S,6R)-5-[(tert-butyldimethylsilyl)oxy]-7-[(1R)-1-(4-methoxyphenyl)ethyl]-7-azabicyclo[4.1.0]hept-3-en-2-one 在 双氧水 、 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 以74%的产率得到(1S,3R,5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octan-2-one
  参考文献：
  名称：

  Use of Aziridines for the Stereocontrolled Synthesis of (−)-LL-C10037α, (+)-MT35214, and (+)-4-epi-MT35214

  摘要：

  Strategies for the synthesis of the title compounds have been developed using a diastereoselective aziridination reaction of 4-O-substituted cyclohexenones. Aziridination using a chiral amine permitted resolution of a 4-hydroxycyclohexane derivative, and this resulted in the synthesis of both enantiomers of the title compound. Alternatively, the chiral 4-hydroxycyclohexenone starting material was derived from quinic acid. In both cases stereoselective epoxidation and opening of the aziridine ring with hydrazoic acid afforded the 2-azidocyclohexenone, which was transformed to the 2-acetamido group present in the natural product.

  DOI：

  10.1021/jo402535j