4-(4-methylenecyclohexyl)phenyl acetate | 1427281-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-(4-methylenecyclohexyl)phenyl acetate
• 英文别名: [4-(4-Methylidenecyclohexyl)phenyl] acetate；[4-(4-methylidenecyclohexyl)phenyl] acetate
• CAS: 1427281-58-0
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: FBLYIPYSMZIZQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-methylenecyclohexyl)phenyl acetate 在 过氧乙酸 、 Mo(acac)2 、 camphor-10-sulfonic acid 、 水 、 双氧水 、 sodium acetate 、 四丁基硫酸氢铵 、 magnesium sulfate 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Comparative Antimalarial Activities and ADME Profiles of Ozonides (1,2,4-trioxolanes) OZ277, OZ439, and Their 1,2-Dioxolane, 1,2,4-Trioxane, and 1,2,4,5-Tetraoxane Isosteres

  摘要：

  To ascertain the structure-activity relationship of the core 1,2,4-trioxolane substructure of dispiro ozonides OZ277 and OZ439, we compared the antimalarial activities and ADME profiles of the 1,2-dioxolane, 1,2,4-trioxane, and 1,2,4,5-tetraoxane isosteres. Consistent with previous data, both dioxolanes had very weak antimalarial properties. For the OZ277 series, the trioxane isostere had the best ADME profile, but its overall antimalarial efficacy was not superior to that of the trioxolane or tetraoxane isosteres. For the OZ439 series, there was a good correlation between the antimalarial efficacy and ADME profiles in the rank order trioxolane > trioxane > tetraoxane. As we have previously observed for OZ439 versus OZ277, the OZ439 series peroxides had superior exposure and efficacy in mice compared to the corresponding OZ277 series peroxides.

  DOI：

  10.1021/jm400004u
• 作为产物：
  描述：

  4-(4-羟基苯基)环己酮 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-(4-methylenecyclohexyl)phenyl acetate
  参考文献：
  名称：

  通过氧化脱芳构化/碘化/[3+2]成环级联构建 Simplicissin 的 A–B–C 环

  摘要：

  作为一种有吸引力的 DMOA 衍生螺萜类化合物，simplicissin 与其他天然类似物具有共同的 A-B-C 环骨架。在氧化脱芳构化/碘化/[3+2]环化级联发展的基础上，成功建立了simplicissin A-B-C环的简明合成途径，并建立了新型氧化脱芳构化/[3+2]环化级联的底物通用性。碘化/[3+2]环化级联已被检查。

  DOI：

  10.1021/acs.orglett.3c03464

文献信息

• Comparative Antimalarial Activities and ADME Profiles of Ozonides (1,2,4-trioxolanes) OZ277, OZ439, and Their 1,2-Dioxolane, 1,2,4-Trioxane, and 1,2,4,5-Tetraoxane Isosteres
  作者：Xiaofang Wang、Yuxiang Dong、Sergio Wittlin、Susan A. Charman、Francis C. K. Chiu、Jacques Chollet、Kasiram Katneni、Janne Mannila、Julia Morizzi、Eileen Ryan、Christian Scheurer、Jessica Steuten、Josefina Santo Tomas、Christopher Snyder、Jonathan L. Vennerstrom

  DOI：10.1021/jm400004u

  日期：2013.3.28

  To ascertain the structure-activity relationship of the core 1,2,4-trioxolane substructure of dispiro ozonides OZ277 and OZ439, we compared the antimalarial activities and ADME profiles of the 1,2-dioxolane, 1,2,4-trioxane, and 1,2,4,5-tetraoxane isosteres. Consistent with previous data, both dioxolanes had very weak antimalarial properties. For the OZ277 series, the trioxane isostere had the best ADME profile, but its overall antimalarial efficacy was not superior to that of the trioxolane or tetraoxane isosteres. For the OZ439 series, there was a good correlation between the antimalarial efficacy and ADME profiles in the rank order trioxolane > trioxane > tetraoxane. As we have previously observed for OZ439 versus OZ277, the OZ439 series peroxides had superior exposure and efficacy in mice compared to the corresponding OZ277 series peroxides.
• Construction of the A–B–C Ring of Simplicissin through an Oxidative Dearomatization/Iodination/[3+2] Annulation Cascade
  作者：Ziwei Zhang、Zezhong Sun、Jianing Song、Hao Guo、Yunxia Wang、Xiangdong Hu

  DOI：10.1021/acs.orglett.3c03464

  日期：2023.12.8

  analogues. On the basis of the development of an oxidative dearomatization/iodination/[3+2] annulation cascade, a concise synthetic pathway to the A–B–C ring of simplicissin has been successfully established, and the substrate generality of the novel oxidative dearomatization/iodination/[3+2] annulation cascade has been checked.

  作为一种有吸引力的 DMOA 衍生螺萜类化合物，simplicissin 与其他天然类似物具有共同的 A-B-C 环骨架。在氧化脱芳构化/碘化/[3+2]环化级联发展的基础上，成功建立了simplicissin A-B-C环的简明合成途径，并建立了新型氧化脱芳构化/[3+2]环化级联的底物通用性。碘化/[3+2]环化级联已被检查。