2-((4-butylphenyl)amino)-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((4-butylphenyl)amino)-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• 英文别名: 2-((4-Butylphenyl)amino)-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione；2-(4-butylanilino)-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: RFYQGKUTWAUUJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-正丁基苯胺 、 (4S)-4-hydroxy-3-methoxy-5-methyl-5,6-epoxycyclohex-2-enone 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 以26.6 mg的产率得到2-((4-butylphenyl)amino)-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Phytotoxic Potential of Secondary Metabolites and Semisynthetic Compounds from Endophytic Fungus Xylaria feejeensis Strain SM3e-1b Isolated from Sapium macrocarpum

  摘要：

  Bioactivity-directed fractionation of the combined culture medium and mycelium extract of the endophytic fungus Xylaria feejeensis strain SM3e-1b, isolated from Sapium macrocarpum, led to the isolation of three known natural products: (4S,5S,6S)-4-hydroxy-3-methoxy-5-methyl-5,6-epoxycyclohex-2-enone or coriloxine, 1; 2-hydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione, 2; and 2,6-dihydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione or fumiquinone B, 3. This is the first report of compound 3 being isolated from this species. Additionally, four new derivatives of coriloxine were prepared: (4R,5S,6R)-6-chloro-4,5-dihydroxy-3-methoxy-5-methylcyclohex-2-enone, 4; 6-hydroxy-5-methyl-3-(methylamino)cyclohexa-2,5- diene-1,4-dione, 5; (4R,5R,6R)-4,5-dihydroxy-3-methoxy-5-methyl-6-(phenylamino)cyclohex-2-enone, 6; and 2-((4-butylphenyl)amino)-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione, 7. X-ray analysis allowed us to unambiguously determine the structures and absolute configuration of semisynthetic derivatives 4, 5, and 6. The phytotoxic activity of the three isolated natural products and the coriloxine derivatives is reported. Germination of the seed, root growth, and oxygen uptake of the seedlings of Trifolium pratense, Medicago sativa, Panicum miliaceum, and Amaranthus hypochondriacus were significantly inhibited by all of the tested compounds. In general, they were more effective inhibiting root elongation than suppressing the germination and seedling oxygen uptake processes as shown by their IC50 values.

  DOI：

  10.1021/acs.jafc.6b01111

文献信息

• Effect of phytotoxic secondary metabolites and semisynthetic compounds from endophytic fungus Xylaria feejeensis strain SM3e-1b on spinach chloroplast photosynthesis
  作者：Martha Lydia Macías-Rubalcava、Marbella Claudia García-Méndez、Beatriz King-Díaz、Norma Angélica Macías-Ruvalcaba

  DOI：10.1016/j.jphotobiol.2016.11.002

  日期：2017.1

  photosynthesis light reactions of three major secondary metabolites produced by the endophytic fungus Xylaria feejeensis strain SM3e-1b, isolated from Sapium macrocarpum; and four novel derivatives of coriloxine, a major compound produced by X. feejeensis. The natural phytotoxins include one epoxycyclohexenone derivative, coriloxine (1), and two quinone derivatives (2–3). The semisynthetic derivatives of coriloxine

  我们研究了从大果ap中分离出的内生真菌Xylaria Feejeensis菌株SM3e-1b产生的三种主要次生代谢产物对光合作用光反应的作用机理；以及四新的Coriloxine衍生物，后者是X. Feejeensis生产的主要化合物。天然植物毒素包括一个epoxycyclohexenone衍生物，coriloxine（1），以及两个醌衍生物（2 - 3）。硅氧烷的半合成衍生物是两个环己烯酮（4 – 6）和两个醌化合物（5 – 7）。环己烯酮（4），（4R，5 S，6 R）-6-氯-4,5-二羟基-3-甲氧基-5-甲基环己-2-烯酮抑制新鲜裂解的菠菜叶绿体从水到MV的ATP合成；它也部分地抑制了基础的和解偶联的光合电子传递，并显着增强了磷酸化电子传递和Mg 2 + -ATPase的活性，从而证明了其作为解偶联剂的作用。另一方面，醌（7），2-（（（4-丁基苯基）氨基）-5-甲氧基-3-甲基环己基2
• Phytotoxic Potential of Secondary Metabolites and Semisynthetic Compounds from Endophytic Fungus <i>Xylaria feejeensis</i> Strain SM3e-1b Isolated from <i>Sapium macrocarpum</i>
  作者：Marbella Claudia García-Méndez、Norma A. Macías-Ruvalcaba、Patricia Lappe-Oliveras、Simón Hernández-Ortega、Martha Lydia Macías-Rubalcava

  DOI：10.1021/acs.jafc.6b01111

  日期：2016.6.1

  Bioactivity-directed fractionation of the combined culture medium and mycelium extract of the endophytic fungus Xylaria feejeensis strain SM3e-1b, isolated from Sapium macrocarpum, led to the isolation of three known natural products: (4S,5S,6S)-4-hydroxy-3-methoxy-5-methyl-5,6-epoxycyclohex-2-enone or coriloxine, 1; 2-hydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione, 2; and 2,6-dihydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione or fumiquinone B, 3. This is the first report of compound 3 being isolated from this species. Additionally, four new derivatives of coriloxine were prepared: (4R,5S,6R)-6-chloro-4,5-dihydroxy-3-methoxy-5-methylcyclohex-2-enone, 4; 6-hydroxy-5-methyl-3-(methylamino)cyclohexa-2,5- diene-1,4-dione, 5; (4R,5R,6R)-4,5-dihydroxy-3-methoxy-5-methyl-6-(phenylamino)cyclohex-2-enone, 6; and 2-((4-butylphenyl)amino)-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione, 7. X-ray analysis allowed us to unambiguously determine the structures and absolute configuration of semisynthetic derivatives 4, 5, and 6. The phytotoxic activity of the three isolated natural products and the coriloxine derivatives is reported. Germination of the seed, root growth, and oxygen uptake of the seedlings of Trifolium pratense, Medicago sativa, Panicum miliaceum, and Amaranthus hypochondriacus were significantly inhibited by all of the tested compounds. In general, they were more effective inhibiting root elongation than suppressing the germination and seedling oxygen uptake processes as shown by their IC50 values.