7-epi-sclerotiorin | 549-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂非酮类
• 英文名称: 7-epi-sclerotiorin
• 英文别名: [(7S)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-7-methyl-6,8-dioxoisochromen-7-yl] acetate
• CAS: 549-23-5；103033-42-7；58976-45-7
• 化学式: C₂₁H₂₃ClO₅
• 分子量: 390.864
• InChiKey: SWJLTKXURNHVHE-SGAXEVNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-epi-sclerotiorin 在 ammonium acetate 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 7-epi-8-O-methylmethylsclerotiorinamine
  参考文献：
  名称：

  Synthesis of the Azaphilones (+)-Sclerotiorin and (+)-8-O-Methylsclerotiorinamine Utilizing (+)-Sparteine Surrogates in Copper-Mediated Oxidative Dearomatization

  摘要：

  Enantioselective syntheses of the azaphilone natural products (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine that possess the natural R-configuration at the quaternary center are reported. The syntheses were accomplished using copper-mediated asymmetric dearomatization employing bis-y-oxo copper complexes prepared from readily available (+)-sparteine surrogates. Of note, site-selective O-methylation of a vinylogous pyridone was used to access the isoquinolin-6(7H)-one core of (+)-8-O-methylsclerotiorinamine.

  DOI：

  10.1021/jo102448n
• 作为产物：
  描述：

  2,4-二甲氧基-3-甲基苯甲醛 在 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 N-氯代丁二酰亚胺 、 copper(l) iodide 、 正丁基锂 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 1,2-二碘乙烷 、 氧气 、 三溴化硼 、 potassium carbonate 、 N,N,N'-三甲基乙二胺 、 三乙胺 、 二异丙胺 、 N,N-二异丙基乙胺 、 鹰爪豆碱 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 62.58h， 生成 7-epi-sclerotiorin
  参考文献：
  名称：

  Synthesis of the Azaphilones (+)-Sclerotiorin and (+)-8-O-Methylsclerotiorinamine Utilizing (+)-Sparteine Surrogates in Copper-Mediated Oxidative Dearomatization

  摘要：

  Enantioselective syntheses of the azaphilone natural products (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine that possess the natural R-configuration at the quaternary center are reported. The syntheses were accomplished using copper-mediated asymmetric dearomatization employing bis-y-oxo copper complexes prepared from readily available (+)-sparteine surrogates. Of note, site-selective O-methylation of a vinylogous pyridone was used to access the isoquinolin-6(7H)-one core of (+)-8-O-methylsclerotiorinamine.

  DOI：

  10.1021/jo102448n

文献信息

• Reengineering an Azaphilone Biosynthesis Pathway in <i>Aspergillus nidulans</i> To Create Lipoxygenase Inhibitors
  作者：Amber D. Somoza、Kuan-Han Lee、Yi-Ming Chiang、Berl R. Oakley、Clay C. C. Wang

  DOI：10.1021/ol203094k

  日期：2012.2.17

  Sclerotiorin, an azaphilone polyketide, is a bioactive natural product known to inhibit 15-lipoxygenase and many other biological targets. To readily access sclerotiorin and analogs, we developed a 2-3 step semisynthetic route to produce a variety of azaphilones starting from an advanced, putative azaphilone intermediate (5) overproduced by an engineered strain of Aspergillus nidulans. The inhibitory activities of the semisynthetic azaphilones against 15-lipoxygenase were evaluated with several compounds displaying low micromolar potency.
• Fujimoto, Haruhiro; Matsudo, Takanoa; Yamaguchi, Akira, Heterocycles, 1990, vol. 30, # 1, p. 607 - 616
  作者：Fujimoto, Haruhiro、Matsudo, Takanoa、Yamaguchi, Akira、Yamazaki, Mikio

  DOI：——

  日期：——
• Synthesis of the Azaphilones (+)-Sclerotiorin and (+)-8-<i>O</i>-Methylsclerotiorinamine Utilizing (+)-Sparteine Surrogates in Copper-Mediated Oxidative Dearomatization
  作者：Andrew R. Germain、Daniel M. Bruggemeyer、Jianglong Zhu、Cedric Genet、Peter O’Brien、John A. Porco

  DOI：10.1021/jo102448n

  日期：2011.4.15

  Enantioselective syntheses of the azaphilone natural products (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine that possess the natural R-configuration at the quaternary center are reported. The syntheses were accomplished using copper-mediated asymmetric dearomatization employing bis-y-oxo copper complexes prepared from readily available (+)-sparteine surrogates. Of note, site-selective O-methylation of a vinylogous pyridone was used to access the isoquinolin-6(7H)-one core of (+)-8-O-methylsclerotiorinamine.