trimethyl(spiro[adamantane-4,3'-diaziridine]-1-yl)silane | 591773-40-9

• 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: trimethyl(spiro[adamantane-4,3'-diaziridine]-1-yl)silane
• CAS: 591773-40-9
• 化学式: C₁₃H₂₄N₂Si
• 分子量: 236.432
• InChiKey: RKOZHRNKIPJPSL-UHFFFAOYSA-N

物化性质

• 沸点：
  291.1±50.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.88
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trimethyl(spiro[adamantane-4,3'-diaziridine]-1-yl)silane 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 4-azi-1-(trimethylsilyl)-adamantane
  参考文献：
  名称：

  Reversal of Diastereoselectivities in Intra- and Intermolecular Reactions of 2-Adamantanylidenes Primarily Caused by Electron-Donating and Electron- Withdrawing Substituents on C5

  摘要：

  A reversal of diastereoselectivity was observed for novel 5-(trimethylsilyl)adamantan-2-ylidene (1c) with regard to 5-hydroxyadamantan-2-ylidene (1a). Ostensibly in intermolecular reactions, 5-substituted 2-adamantanylidenes (1) are sterically unbiased. However, inductive effects originating from the pendant group bend the divalent carbon bridge of 1 either toward (ERG's, e.g., -Si(CH3)(3)) or away from (EWG's, e.g., -OH) the gamma-position. Hence, the more exposed side is more susceptible to intermolecular reaction and the other side concomitantly undergoes intramolecular 1,3-CH insertions more readily.

  DOI：

  10.1021/ol0350700
• 作为产物：
  描述：

  5-(trimethylsilyl)adamantan-2-one ethylene ketal 在 盐酸 、 氨 、 hydroxylamine-O-sulfonic acid 作用下， 以 甲醇 为溶剂， 生成 trimethyl(spiro[adamantane-4,3'-diaziridine]-1-yl)silane
  参考文献：
  名称：

  Reversal of Diastereoselectivities in Intra- and Intermolecular Reactions of 2-Adamantanylidenes Primarily Caused by Electron-Donating and Electron- Withdrawing Substituents on C5

  摘要：

  A reversal of diastereoselectivity was observed for novel 5-(trimethylsilyl)adamantan-2-ylidene (1c) with regard to 5-hydroxyadamantan-2-ylidene (1a). Ostensibly in intermolecular reactions, 5-substituted 2-adamantanylidenes (1) are sterically unbiased. However, inductive effects originating from the pendant group bend the divalent carbon bridge of 1 either toward (ERG's, e.g., -Si(CH3)(3)) or away from (EWG's, e.g., -OH) the gamma-position. Hence, the more exposed side is more susceptible to intermolecular reaction and the other side concomitantly undergoes intramolecular 1,3-CH insertions more readily.

  DOI：

  10.1021/ol0350700