2-hydroxy-3-methyl-6-phenethyl-1,4-benzoquinone | 1310708-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-3-methyl-6-phenethyl-1,4-benzoquinone
• CAS: 1310708-29-2
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: NSDXXVBYDGKWQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-methyl-6-phenethyl-1,4-benzoquinone 在 sodium dithionite 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以100%的产率得到3-methyl-6-phenethylbenzene-1,2,4-triol
  参考文献：
  名称：

  Synthesis of Parvistemin A via Biomimetic Oxidative Dimerization

  摘要：

  The first synthesis of the naturally occurring benzoquinone dimer parvistemin A is reported. The key step is the late stage iron(III) mediated dimerization of a 1,2,4-trihydroxyarene to give the natural product in good yield, a phenol oxidative coupling that is believed to be biomimetic. The route proceeds in seven steps from an inexpensive commercially available acetophenone in 14% overall yield.

  DOI：

  10.1021/ol201246e
• 作为产物：
  描述：

  3-methyl-6-phenethylbenzene-1,2,4-triol 在 FeCl₃/SiO₂ 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.17h， 以55%的产率得到parvistemin A
  参考文献：
  名称：

  Synthesis of Parvistemin A via Biomimetic Oxidative Dimerization

  摘要：

  The first synthesis of the naturally occurring benzoquinone dimer parvistemin A is reported. The key step is the late stage iron(III) mediated dimerization of a 1,2,4-trihydroxyarene to give the natural product in good yield, a phenol oxidative coupling that is believed to be biomimetic. The route proceeds in seven steps from an inexpensive commercially available acetophenone in 14% overall yield.

  DOI：

  10.1021/ol201246e