2-tert-butyl-5-(2-cyclohexen-1-yl)-2,5-cyclohexadiene-1,4-dione | 1207096-45-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-tert-butyl-5-(2-cyclohexen-1-yl)-2,5-cyclohexadiene-1,4-dione
• 英文别名: 2-tert-butyl-5-(cyclohex-1-en-3-yl)-1,4-quinone；2-Tert-butyl-5-cyclohex-2-en-1-ylcyclohexa-2,5-diene-1,4-dione
• CAS: 1207096-45-4
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: IICTVKAADZJYHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-tert-butyl-5-(2-cyclohexen-1-yl)-2,5-cyclohexadiene-1,4-dione 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以92%的产率得到2-tert-butyl-5-cyclohexyl-1,4-quinone
  参考文献：
  名称：

  Synthesis and inhibitory evaluation of cyclohexen-2-yl- and cyclohexyl-substituted phenols and quinones to endothelial cell and cancer cells

  摘要：

  Alkylanon of phenols with 1,3-cyclohexadiene (1) has been conducted and a series of cyclohexen-2-yl- and cyclohexyl-substituted phenols and quinones were screened against the proliferation of HUVEC and cancer cells. Phenol type as well as the size and occupied position of the substitute are important for the alkylating reaction and the inhibitory activity and selectivity of a compound. 2,5-Di(cyclohexen-2-yl)benzene-1,4-diol (25) bearing two cyclohexen-2-yl groups and 2-tert-butyl-5-(cyclohexen-2-yl)benzene-1,4-diol (30) bearing cyclohexen-2-yl and tert-butyl groups exhibited good selectivity against HUVEC pioliferation (IC(50)s of 2 0 and 1 4 mu M, respectively) with relatively low toxicity to ccc-HPF-1.

  DOI：

  10.1016/j.ejmech.2010.01.051
• 作为产物：
  描述：

  叔丁基对苯醌 在 hafnium tetrakis(trifluoromethanesulfonate) 、 二氢吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-tert-butyl-5-(2-cyclohexen-1-yl)-2,5-cyclohexadiene-1,4-dione
  参考文献：
  名称：

  对苯二酚通过氧化还原链反应的催化亲电烷基化

  摘要：

  对苯醌的烯丙基化和苄基化是通过不寻常的氧化还原链反应实现的。机理研究表明，痕量对苯二酚的存在会引发氧化还原链反应，该反应由路易斯酸催化的Friedel-Crafts烷基化反应和随后的氧化还原平衡而重新生成对苯二酚。亲电子试剂可以是各种烯丙基和苄基酯。Hantzsch酯作为引发剂的添加提高了反应效率。

  DOI：

  10.1002/anie.201702885

文献信息

• Catalytic Electrophilic Alkylation of<i>p</i>-Quinones through a Redox Chain Reaction
  作者：Xiao-Long Xu、Zhi Li

  DOI：10.1002/anie.201702885

  日期：2017.7.3

  Allylation and benzylation of p‐quinones was achieved through an unusual redox chain reaction. Mechanistic studies suggest that the existence of trace hydroquinone initiates a redox chain reaction that consists of a Lewis acid catalyzed Friedel–Crafts alkylation and a subsequent redox equilibrium that regenerates hydroquinone. The electrophiles could be various allylic and benzylic esters. The addition

  对苯醌的烯丙基化和苄基化是通过不寻常的氧化还原链反应实现的。机理研究表明，痕量对苯二酚的存在会引发氧化还原链反应，该反应由路易斯酸催化的Friedel-Crafts烷基化反应和随后的氧化还原平衡而重新生成对苯二酚。亲电子试剂可以是各种烯丙基和苄基酯。Hantzsch酯作为引发剂的添加提高了反应效率。
• Synthesis and inhibitory evaluation of cyclohexen-2-yl- and cyclohexyl-substituted phenols and quinones to endothelial cell and cancer cells
  作者：Xin Liu、Yingyong Ou、Shaopeng Chen、Xin Lu、Hao Cheng、Xian Jia、Decai Wang、Guo-Chun Zhou

  DOI：10.1016/j.ejmech.2010.01.051

  日期：2010.6

  Alkylanon of phenols with 1,3-cyclohexadiene (1) has been conducted and a series of cyclohexen-2-yl- and cyclohexyl-substituted phenols and quinones were screened against the proliferation of HUVEC and cancer cells. Phenol type as well as the size and occupied position of the substitute are important for the alkylating reaction and the inhibitory activity and selectivity of a compound. 2,5-Di(cyclohexen-2-yl)benzene-1,4-diol (25) bearing two cyclohexen-2-yl groups and 2-tert-butyl-5-(cyclohexen-2-yl)benzene-1,4-diol (30) bearing cyclohexen-2-yl and tert-butyl groups exhibited good selectivity against HUVEC pioliferation (IC(50)s of 2 0 and 1 4 mu M, respectively) with relatively low toxicity to ccc-HPF-1.