2-methoxyprop-2-yl 2-[(1S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]eth-1-yl peroxide | 419568-92-6

• 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 2-[(1S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]eth-1-yl peroxide
• 英文别名: (1R,5S)-2-[2-(2-methoxypropan-2-ylperoxy)ethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene
• CAS: 419568-92-6
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: NKNSZYHRPNHCIT-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 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 2-[(1S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]eth-1-yl peroxide 在 2,6-二叔丁基-4-甲基苯酚 、 溶剂黄146 作用下， 以97%的产率得到(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
• 作为产物：
  描述：

  (1R)-nopol tosylate 在 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 482.0h， 生成 2-methoxyprop-2-yl 2-[(1S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]eth-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 and in vitro Trichomonacidal activities of some new dialkylperoxides and 1,2,4-trioxanes
  作者：B Camuzat-Dedenis

  DOI：10.1016/s0223-5234(01)01278-8

  日期：2001.10

  Two series of three trioxanes and 18 disubstituted peroxides were synthesised and evaluated for their in vitro trichomonacidal activity against Trichomonas vaginalis. The most active compound, 2-methylprop-2-yl 2-methoxyeth-1-yl peroxide exhibited an IC(50) value of 1.0+/-0.2 microM whereas other dialkyl peroxides had various IC(50) values which could not be correlated to their molecule structure.

  合成了两个系列的三个三恶烷和18个双取代的过氧化物，并评估了它们对阴道毛滴虫的体外毛滴酸活性。最具活性的化合物2-甲基丙-2-基2-甲氧基乙基-1-基过氧化物的IC（50）值为1.0 +/- 0.2 microM，而其他二烷基过氧化物具有的各种IC（50）值则无法关联他们的分子结构。最好的化合物的活性约为甲硝唑的五倍。产生的氧或自由基的量不能完全解释活性，表明这些化合物对阴道锥虫的另一种作用方式。
• 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.