1-(azido(tert-butylperoxy)methyl)-3-(cyclopentyloxy)benzene | 1447824-50-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(azido(tert-butylperoxy)methyl)-3-(cyclopentyloxy)benzene
• 英文别名: 1-[Azido(tert-butylperoxy)methyl]-3-cyclopentyloxybenzene；1-[azido(tert-butylperoxy)methyl]-3-cyclopentyloxybenzene
• CAS: 1447824-50-1；1447824-74-9
• 化学式: C₁₆H₂₃N₃O₃
• 分子量: 305.377
• InChiKey: XKSHQUPZPWUREB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(azido(tert-butylperoxy)methyl)-3-(cyclopentyloxy)benzene 在 (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan) 作用下， 以 乙酸乙酯 为溶剂， 反应 14.0h， 以35%的产率得到1-(azido(tert-butylperoxy)methyl)-3-(cyclopentyloxy)benzene
  参考文献：
  名称：

  Synthesis and Asymmetric Resolution of α-Azido-peroxides

  摘要：

  An unprecedented synthesis of alpha-azido-peroxides has been developed using an FeCl3-catalyst starting from carbonyl, TMS-azide, and hydroperoxide. Further, a base promoted decomposition of synthesized secondary alpha-azido-peroxides to provide the corresponding tert-butyl esters has been disclosed. Finally, an asymmetric kinetic resolution of such alpha-azido-peroxides has also been developed to provide chiral a-azido-peroxides in excellent enantiopurity.

  DOI：

  10.1021/ol401443a
• 作为产物：
  描述：

  叔丁基过氧化氢 、 3-环戊基氧基-苯甲醛 在 iron(III) chloride 、 叠氮基三甲基硅烷 作用下， 以 癸烷 、 二氯甲烷 为溶剂， 反应 1.5h， 以68%的产率得到1-(azido(tert-butylperoxy)methyl)-3-(cyclopentyloxy)benzene
  参考文献：
  名称：

  Synthesis and Asymmetric Resolution of α-Azido-peroxides

  摘要：

  An unprecedented synthesis of alpha-azido-peroxides has been developed using an FeCl3-catalyst starting from carbonyl, TMS-azide, and hydroperoxide. Further, a base promoted decomposition of synthesized secondary alpha-azido-peroxides to provide the corresponding tert-butyl esters has been disclosed. Finally, an asymmetric kinetic resolution of such alpha-azido-peroxides has also been developed to provide chiral a-azido-peroxides in excellent enantiopurity.

  DOI：

  10.1021/ol401443a

文献信息

• Synthesis and Asymmetric Resolution of α-Azido-peroxides
  作者：Suman Pramanik、Prasanta Ghorai

  DOI：10.1021/ol401443a

  日期：2013.8.2

  An unprecedented synthesis of alpha-azido-peroxides has been developed using an FeCl3-catalyst starting from carbonyl, TMS-azide, and hydroperoxide. Further, a base promoted decomposition of synthesized secondary alpha-azido-peroxides to provide the corresponding tert-butyl esters has been disclosed. Finally, an asymmetric kinetic resolution of such alpha-azido-peroxides has also been developed to provide chiral a-azido-peroxides in excellent enantiopurity.