((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)(3-ethyl-2-((trimethylsilyl)oxy)isoxazolidin-5-yl)methanone | 133705-97-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)(3-ethyl-2-((trimethylsilyl)oxy)isoxazolidin-5-yl)methanone
• CAS: 133705-97-2；139491-32-0；139491-44-4；139491-45-5；139491-46-6
• 化学式: C₁₉H₃₄N₂O₅SSi
• 分子量: 430.641
• InChiKey: RAGKMTHCMAWGQR-IWJNZZSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  76.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)(3-ethyl-2-((trimethylsilyl)oxy)isoxazolidin-5-yl)methanone 在 L-Selectride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.33h， 生成 5-异噻唑甲醇,3-乙基-4,5-二氢-,(R)-
  参考文献：
  名称：

  Asymmetric silyl nitronate cycloadditions with bornane-10,2-sultam derivatives

  摘要：

  Asymmetric silyl nitronate cycloadditions with N-acryloyl (2R)-bornane-10,2-sultam, N-acryloyl (2S)-bornane-10,2-sultam, and N-methacryloyl (2R)-bornane-10,2-sultam have been studied. The asymmetric silyl nitronate cycloaddition/elimination methodology provides a general route for the asymmetric synthesis of 2-isoxazolines.

  DOI：

  10.1016/s0957-4166(00)80032-4
• 作为产物：
  描述：

  N-<(4,5-dihydro-3-methyl-(5R)-5-isoxazolyl)carbonyl>-(2R)-bornane-10,2-sultam 在 L-Selectride 、 sodium hydride 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 25.75h， 生成 ((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)(3-ethyl-2-((trimethylsilyl)oxy)isoxazolidin-5-yl)methanone
  参考文献：
  名称：

  Asymmetric silyl nitronate cycloadditions with bornane-10,2-sultam derivatives

  摘要：

  Asymmetric silyl nitronate cycloadditions with N-acryloyl (2R)-bornane-10,2-sultam, N-acryloyl (2S)-bornane-10,2-sultam, and N-methacryloyl (2R)-bornane-10,2-sultam have been studied. The asymmetric silyl nitronate cycloaddition/elimination methodology provides a general route for the asymmetric synthesis of 2-isoxazolines.

  DOI：

  10.1016/s0957-4166(00)80032-4

文献信息

• Asymmetric induction in silyl nitronate cycloadditions to Oppolzer's chiral sultam derivatives
  作者：Byeang Hyean Kim、Ju Young Lee、Kimoon Kim、Dongmok Whang

  DOI：10.1016/s0957-4166(00)82151-5

  日期：1991.1

  Silyl nitronate cycloadditions to Oppolzer's chiral sultam derivatives, followed by the elimination of the sily alcohols from the resulting N-silyloxyisoxazolidines, provide DELTA-2-isoxazolines in good stereoselectivity (ca. 89/11). The favored transition state is suggested in the light of the X-ray crystal structure of a major cycloadduct.