(1R,5S)-2-(2-hydroperoxyethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene | 474070-42-3

• 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: (1R,5S)-2-(2-hydroperoxyethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene
• CAS: 474070-42-3
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: SJDQWYOWQZZFMK-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,5S)-2-(2-hydroperoxyethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene 在 吡啶 、 二-叔-丁基过氧草酸酯 、 氧气 、 乙酸酐 作用下， 以 苯 为溶剂， 生成 (1R,2R,5R)-6,6-dimethylspiro[bicyclo[3.1.1]heptane-2,3'-dioxolane]-3-one
  参考文献：
  名称：

  Synthesis of cardamom peroxide analogues by radical cyclization of hydroperoxyalkenes

  摘要：

  Three pinenic hydroperoxides were synthesized according to the Dussault method. Two of them could cyclize under radical conditions to give the exo-trig isomer as a single regioisomer. Only five- and six-member ring peroxides were obtained, whereas none of the possible seven-member ones was observed. This strategy could be employed in the total synthesis of cardamom peroxide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01122-x
• 作为产物：
  描述：

  nopyl bromide 在 cesium hydroxide 、 2,6-二叔丁基-4-甲基苯酚 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 480.0h， 生成 (1R,5S)-2-(2-hydroperoxyethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene
  参考文献：
  名称：

  Synthesis of cardamom peroxide analogues by radical cyclization of hydroperoxyalkenes

  摘要：

  Three pinenic hydroperoxides were synthesized according to the Dussault method. Two of them could cyclize under radical conditions to give the exo-trig isomer as a single regioisomer. Only five- and six-member ring peroxides were obtained, whereas none of the possible seven-member ones was observed. This strategy could be employed in the total synthesis of cardamom peroxide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01122-x

文献信息

• Synthesis of cardamom peroxide analogues by radical cyclization of hydroperoxyalkenes
  作者：Laure Cointeaux、Jean-François Berrien、Joëlle Mayrargue

  DOI：10.1016/s0040-4039(02)01122-x

  日期：2002.8

  Three pinenic hydroperoxides were synthesized according to the Dussault method. Two of them could cyclize under radical conditions to give the exo-trig isomer as a single regioisomer. Only five- and six-member ring peroxides were obtained, whereas none of the possible seven-member ones was observed. This strategy could be employed in the total synthesis of cardamom peroxide. (C) 2002 Elsevier Science Ltd. All rights reserved.