(-)-(1R)-6,6-Dimethylbicyclo<3.1.1>hept-2-ene-2-propyl 4-toluenesulfonate | 144342-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-(1R)-6,6-Dimethylbicyclo<3.1.1>hept-2-ene-2-propyl 4-toluenesulfonate
• 英文别名: (1S)-4-(6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-2-yl)-but-1-yl-tosylate；(-)-(1R)-6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-propyl 4-toluenesulfonate
• CAS: 144342-20-1
• 化学式: C₁₉H₂₆O₃S
• 分子量: 334.48
• InChiKey: LVDCSDIUHWQDPN-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (-)-(1R)-6,6-Dimethylbicyclo<3.1.1>hept-2-ene-2-propyl 4-toluenesulfonate 在 cesium hydroxide 、 二-叔-丁基过氧草酸酯 、 2,6-二叔丁基-4-甲基苯酚 、 氧气 、 溶剂黄146 、 sodium bromide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 186.0h， 生成
  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)6,6-二甲基联环(3.1.1)庚烷-2-烯-2-乙醇 在 吡啶 、 magnesium 、 sodium bromide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 11.0h， 生成 (-)-(1R)-6,6-Dimethylbicyclo<3.1.1>hept-2-ene-2-propyl 4-toluenesulfonate
  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

• Preparation of Campholenal Analogues: Chirons for the lipophilic moiety of sandalwood-like odorant alcohols
  作者：Christian Chapuis、Robert Brauchli

  DOI：10.1002/hlca.19920750507

  日期：1992.8.13

  In connection with structure-activity relationship studies, analogues of campholenal ((+)-4b), an important building block for sandalwood-like odorants, were prepared. The five-membered-ring analogues 4 were obtained by epoxidation of the corresponding α-pinene derivatives 2, followed by catalytic ZnBr2 isomerisation (Scheme 2). The six-membered-ring skeleton was obtained by ozonolysis of α-campholenyl

  结合结构-活性关系研究，制备了樟脑类似物（（+）- 4b），它是檀香状增香剂的重要组成部分。通过将相应的α- by烯衍生物2环氧化，然后进行催化的ZnBr 2异构化（流程2），获得五元环类似物4。通过臭氧分解α-樟脑烯基乙酸酯（（-）- 14b），然后进行分子内羟醛缩合，获得六元环骨架（方案5）。给出13 C-NMR分配。
• 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.