1,3-Diacetoxy-5,7-dimethyl-adamantan | 20366-07-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3-Diacetoxy-5,7-dimethyl-adamantan
• 英文别名: (3-Acetyloxy-5,7-dimethyl-1-adamantyl) acetate
• CAS: 20366-07-8
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: CUZHDLZZCCPIFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酸异丙烯酯 、 1,3-二羟基-5,7-二甲基金刚烷 在 Cp*2Sm(THF)2 、 cyclohexanone oxime acetate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以99%的产率得到1,3-Diacetoxy-5,7-dimethyl-adamantan
  参考文献：
  名称：

  An Efficient Acylation of Tertiary Alcohols with Isopropenyl Acetate Mediated by an Oxime Ester and Cp*₂Sm(thf)₂

  摘要：

  An efficient method for the acylation of tertiary alcohols with isopropenyl acetate (1) by the use of an oxime and Cp*Sm-2(thf)(2) as catalyst was developed. Thus, various types of tertiary alcohols could be acylated with 1 in the presence of a catalytic amount of cyclohexanone oxime acetate (2) and Cp*Sm-2(thf)(2) under mild conditions to form the corresponding acetates in excellent yields. Acid-sensitive terpene alcohols such as linalool were successfully acetylated by the present method to give acetyl linalool in quantitative yield. This method enables an alternative acylation of tertiary alcohols under acid-free conditions.

  DOI：

  10.1021/jo971204+

文献信息

• An Efficient Acylation of Tertiary Alcohols with Isopropenyl Acetate Mediated by an Oxime Ester and Cp*₂Sm(thf)₂
  作者：Daisuke Tashiro、Yumi Kawasaki、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1021/jo971204+

  日期：1997.11.1

  An efficient method for the acylation of tertiary alcohols with isopropenyl acetate (1) by the use of an oxime and Cp*Sm-2(thf)(2) as catalyst was developed. Thus, various types of tertiary alcohols could be acylated with 1 in the presence of a catalytic amount of cyclohexanone oxime acetate (2) and Cp*Sm-2(thf)(2) under mild conditions to form the corresponding acetates in excellent yields. Acid-sensitive terpene alcohols such as linalool were successfully acetylated by the present method to give acetyl linalool in quantitative yield. This method enables an alternative acylation of tertiary alcohols under acid-free conditions.