2-heptyl-6-methoxy-1,4-benzoquinone | 107811-51-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-heptyl-6-methoxy-1,4-benzoquinone
• 英文别名: 2-Methoxy-6-heptyl-1,4-benzoquinone；2,5-Cyclohexadiene-1,4-dione, 2-heptyl-6-methoxy-；2-heptyl-6-methoxycyclohexa-2,5-diene-1,4-dione
• CAS: 107811-51-8
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: FVLYRFSEEUSOAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-heptyl-6-methoxyphenol 在 potassium nitrososulfonate 、 borate buffer pH 9 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以24%的产率得到2-heptyl-6-methoxy-1,4-benzoquinone
  参考文献：
  名称：

  Koenig, Wilfried A.; Faasch, Holger; Heitsch, Holger, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1993, vol. 48, # 3, p. 387 - 393

  摘要：

  DOI：

文献信息

• Isolation, Synthesis, and Structure−Activity Relationships of Bioactive Benzoquinones from <i>Miconia lepidota</i> from the Suriname Rainforest
  作者：A. A. Leslie Gunatilaka、John M. Berger、Randy Evans、James S. Miller、Jan H. Wisse、Kim M. Neddermann、Isia Bursuker、David G. I. Kingston

  DOI：10.1021/np000219r

  日期：2001.1.1

  Bioactivity-directed fractionation of an EtOAc extract from the leaves of Miconia lepidota afforded the two benzoquinones 2-methoxy-6-heptyl-1,4-benzoquinone (1) and 2-methoxy-6-pentyl-1,4-benzoquinone (primin) (2). This is the first reported isolation of 1. Both quinones 1 and 2 exhibited activity toward mutant yeast strains based on Saccharomyces cerevisiae, indicative of their cytotoxicity and potential anticancer activity. A number of previously synthesized and new analogues were prepared and tested in the same strains. Compounds 1, 2, 2-methoxy-6-butyl-1,4-benzoquinone (5), and 2-methoxy-6-decyl-1,4-benzoquinone (6) were tested in two cytotoxicity assays. In the M109 tumor cell lines, quinones 1, 2, and 6 had an IC50 value of 10 mug/mL. In the A2780 cell line, compounds 1, 2 and 5 had IC50 values of 7.9, 2.9, and 3.2 mug/mL, respectively.
• Koenig, Wilfried A.; Faasch, Holger; Heitsch, Holger, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1993, vol. 48, # 3, p. 387 - 393
  作者：Koenig, Wilfried A.、Faasch, Holger、Heitsch, Holger、Colberg, Cornelia、Hausen, Bjoern M.

  DOI：——

  日期：——