5-(trimethylsilyl)adamantan-2-one ethylene ketal | 121498-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(trimethylsilyl)adamantan-2-one ethylene ketal
• 英文别名: trimethyl(spiro[1,3-dioxolane-2,4'-adamantane]-1'-yl)silane
• CAS: 121498-03-1
• 化学式: C₁₅H₂₆O₂Si
• 分子量: 266.456
• InChiKey: WOTKXYSNKYMEOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  18.0
• 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：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-(trimethylsilyl)adamantan-2-one ethylene ketal 在 chromium(VI) oxide 、 盐酸 、 硫酸 、 氨 、 hydroxylamine-O-sulfonic acid 作用下， 以 甲醇 、 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：

  金刚烷酮 在 氢溴酸 、 甲基锂 、 硝酸 、 对甲苯磺酸 作用下， 以 六甲基磷酰三胺 、 乙醚 、 甲苯 为溶剂， 生成 5-(trimethylsilyl)adamantan-2-one ethylene ketal
  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

文献信息

• Stereochemistry of reduction and methylation of 5-(trimethylsilyl)adamantan-2-one and 5-(trimethylstannyl)adamantan-2-one
  作者：Mei Xie、W. J. Le Noble

  DOI：10.1021/jo00277a018

  日期：1989.8