2-methoxyprop-2-yl-3-[(1S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl]-prop-1-yl-peroxide | 461417-88-9

• 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: 2-methoxyprop-2-yl-3-[(1S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl]-prop-1-yl-peroxide
• 英文别名: (1R,5S)-2-[3-(2-methoxypropan-2-ylperoxy)propyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene
• CAS: 461417-88-9
• 化学式: C₁₆H₂₈O₃
• 分子量: 268.397
• InChiKey: KTUFXCGXXJPFFZ-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxyprop-2-yl-3-[(1S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl]-prop-1-yl-peroxide 在 2,6-二叔丁基-4-甲基苯酚 、 溶剂黄146 作用下， 以98%的产率得到3-[(1S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl]-propyl hydroperoxide
  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：

  (1S)-homonopol 在 吡啶 、 cesium hydroxide 、 sodium bromide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 189.0h， 生成 2-methoxyprop-2-yl-3-[(1S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl]-prop-1-yl-peroxide
  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.
• Synthesis and trichomonacidal activity of perketals and hydroperoxides
  作者：L. Cointeaux、J.-F. Berrien、B. Camuzat-Dedenis、V. Peyrou、O. Provot、C. Bories、P.M. Loiseau、J. Mayrargue

  DOI：10.1016/s0014-827x(02)01238-7

  日期：2002.5

  Some perketals were synthesized by the Dussault procedure using simple bromides and 2-methoxyprop-2-yl hydroperoxide. Treatment with acetic acid gave the corresponding hydroperoxides. Both perketals and hydroperoxides were tested in vitro as trichomonacidal agents. Most of them exhibited very good activities. Them most powerful compound was 2-methoxyprop-2-yl hexadec-1-yl peroxide which exhibited an IC50 value of 0.51 muM being 10 times more effective than the reference compound Metronidazole. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.