1-methoxy-3-(1-methylethenyl)cyclohexyl hydroperoxide | 364593-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氢过氧化物
• 英文名称: 1-methoxy-3-(1-methylethenyl)cyclohexyl hydroperoxide
• 英文别名: 1-Hydroperoxy-1-methoxy-3-prop-1-en-2-ylcyclohexane；1-hydroperoxy-1-methoxy-3-prop-1-en-2-ylcyclohexane
• CAS: 364593-90-8
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: JSEUDXARBYTIKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methoxy-3-(1-methylethenyl)cyclohexyl hydroperoxide 在 2,2,2-三氟乙醇 、 臭氧 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-methoxy-4-methyl-1-methyldioxy-2,3-dioxabicyclo[3.3.1]nonane
  参考文献：
  名称：

  Yingzhaosu A analogues: synthesis by the ozonolysis of unsaturated hydroperoxides, structural analysis and determination of anti-malarial activity

  摘要：

  Ozone-mediated cyclization of a series of unsaturated hydroperoxides 7, prepared from dienes 2, afforded the corresponding yingzhaosu A analogues 9 in moderate to high yield. X-Ray crystallographic analysis of two yingzhaosu A analogues, endo-9f and 13, showed that the 2,3-dioxabicyclo[3,3,1]nonane system adopts a chair-boat arrangement. Subsequent treatment of endoperoxides 9 with Ag2O/MeI afforded the expected methyldioxy-substituted cyclic peroxides 14, several of which showed notable anti-malarial activity against P. falciparum in vitro. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00557-9
• 作为产物：
  描述：

  1-Isopropenyl-3-[1-methoxy-meth-(Z)-ylidene]-cyclohexane 在 臭氧 作用下， 以 甲醇 为溶剂， 以67%的产率得到1-methoxy-3-(1-methylethenyl)cyclohexyl hydroperoxide
  参考文献：
  名称：

  不饱和氢过氧乙缩醛应召素A类似物的合成及抗疟活性

  摘要：

  乙烯基醚的臭氧分解2，从dihydrocarvone制备1（1：4混合物的顺式-和反式-异构体），在甲醇中，得到两种异构体的不饱和氢过氧缩醛顺-和反式- 3。碘鎓离子或氢过氧化物的臭氧介导的环化反应的顺式- 3，得到相应的鹰爪甲类似物4和6在中等产率。由Ag 2 O介导的6的甲基化获得的过氧化物8在体外具有显着的抗疟疾活性（IC 50 = 1.0×10-7 M）。

  DOI：

  10.1016/s0040-4039(00)00372-5

文献信息

• Antimalarial Activity of Yingzhaosu A Analogues
  作者：Hye-Sook Kim、Khurshida Begum、Naoki Ogura、Yusuke Wataya、Takahiro Tokuyasu、Araki Masuyama、Masatomo Nojima、Kevin J. McCullough

  DOI：10.1021/jm020208q

  日期：2002.10.1

  hydroperoxides 1 afforded the expected yingzhaosu A analogues 2. In some cases, however, the corresponding cyclic ethers 5 were formed competitively with the cyclic peroxides 2, the ratios of these two products being a marked function of the structure of the starting materials. Some of the cyclic peroxides 2 showed significant antimalarial activities in vitro and in vivo.

  碘鎓离子介导的不饱和氢过氧化物1的环化提供了预期的yingzhaosu A类似物2。然而，在某些情况下，相应的环醚5与环过氧化物2竞争地形成，这两种产物的比率是其结构的显着函数起始材料。一些环状过氧化物2在体外和体内均表现出显着的抗疟活性。
• Synthesis and anti-malarial activity of yingzhaosu A analogues from unsaturated hydroperoxy acetals
  作者：Takahiro Tokuyasu、Araki Masuyama、Masatomo Nojima、Hye-Sook Kim、Yusuke Wataya

  DOI：10.1016/s0040-4039(00)00372-5

  日期：2000.4

  Ozonolysis of a vinyl ether 2, prepared from dihydrocarvone 1 (a 1:4 mixture of cis- and trans-isomer), in methanol gave two isomeric unsaturated hydroperoxy acetals cis- and trans-3. Iodonium ion- or ozone-mediated cyclizations of the hydroperoxide cis-3 gave the corresponding yingzhaosu A analogues 4 and 6 in moderate yields. The peroxide 8, obtained by the Ag2O-mediated methylation of 6, showed

  乙烯基醚的臭氧分解2，从dihydrocarvone制备1（1：4混合物的顺式-和反式-异构体），在甲醇中，得到两种异构体的不饱和氢过氧缩醛顺-和反式- 3。碘鎓离子或氢过氧化物的臭氧介导的环化反应的顺式- 3，得到相应的鹰爪甲类似物4和6在中等产率。由Ag 2 O介导的6的甲基化获得的过氧化物8在体外具有显着的抗疟疾活性（IC 50 = 1.0×10-7 M）。
• Yingzhaosu A analogues: synthesis by the ozonolysis of unsaturated hydroperoxides, structural analysis and determination of anti-malarial activity
  作者：Takahiro Tokuyasu、Araki Masuyama、Masatomo Nojima、Kevin J McCullough、Hye-Sook Kim、Yusuke Wataya

  DOI：10.1016/s0040-4020(01)00557-9

  日期：2001.7

  Ozone-mediated cyclization of a series of unsaturated hydroperoxides 7, prepared from dienes 2, afforded the corresponding yingzhaosu A analogues 9 in moderate to high yield. X-Ray crystallographic analysis of two yingzhaosu A analogues, endo-9f and 13, showed that the 2,3-dioxabicyclo[3,3,1]nonane system adopts a chair-boat arrangement. Subsequent treatment of endoperoxides 9 with Ag2O/MeI afforded the expected methyldioxy-substituted cyclic peroxides 14, several of which showed notable anti-malarial activity against P. falciparum in vitro. (C) 2001 Elsevier Science Ltd. All rights reserved.