2-(azido(tert-butylperoxy)methyl)naphthalene | 1447824-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(azido(tert-butylperoxy)methyl)naphthalene
• CAS: 1447824-53-4
• 化学式: C₁₅H₁₇N₃O₂
• 分子量: 271.319
• InChiKey: KWVXJMLGQJCNPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.22
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(azido(tert-butylperoxy)methyl)naphthalene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 以191.5 mg的产率得到tert-butyl 2-naphthoate
  参考文献：
  名称：

  Intramolecular Rearrangement of α-Azidoperoxides: An Efficient Synthesis of tert-Butyl Esters

  摘要：

  An unprecedented intramolecular rearrangement of alpha-azidoperoxides, promoted by simple organic base to provide tert-butyl esters, has been presented. Further, a one-pot methodology consisting of in situ generation of the a-azidoperoxides from corresponding aldehydes followed by base-promoted rearrangement to obtain the desired ester has also been executed. Relevant mechanistic studies, to provide the proof for intramolecular alkoxy transfer, are investigated.

  DOI：

  10.1021/acs.orglett.5b00190
• 作为产物：
  描述：

  叔丁基过氧化氢 、 2-萘甲醛 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 1.0h， 生成 2-(azido(tert-butylperoxy)methyl)naphthalene
  参考文献：
  名称：

  Intramolecular Rearrangement of α-Azidoperoxides: An Efficient Synthesis of tert-Butyl Esters

  摘要：

  An unprecedented intramolecular rearrangement of alpha-azidoperoxides, promoted by simple organic base to provide tert-butyl esters, has been presented. Further, a one-pot methodology consisting of in situ generation of the a-azidoperoxides from corresponding aldehydes followed by base-promoted rearrangement to obtain the desired ester has also been executed. Relevant mechanistic studies, to provide the proof for intramolecular alkoxy transfer, are investigated.

  DOI：

  10.1021/acs.orglett.5b00190

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.