6-[(3E,5E,7S)-5,7-dimethylnona-3,5-dien-1-ynyl]-2,4-dihydroxy-3-methylbenzaldehyde | 1277176-10-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-[(3E,5E,7S)-5,7-dimethylnona-3,5-dien-1-ynyl]-2,4-dihydroxy-3-methylbenzaldehyde
• CAS: 1277176-10-9
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: JJYOPLACOGBJOG-ONXIXHNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-[(3E,5E,7S)-5,7-dimethylnona-3,5-dien-1-ynyl]-2,4-dihydroxy-3-methylbenzaldehyde 在 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 氧气 、 N,N-二异丙基乙胺 、 (1R,2S,9S)-11-ethyl-7,11-diazatricyclo[7.3.1.0^2,7]tridecane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 31.58h， 生成 (+)-N-methylsclerotiorinamine
  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 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 1,2-二碘乙烷 、 三溴化硼 、 potassium carbonate 、 N,N,N'-三甲基乙二胺 、 三乙胺 、 二异丙胺 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 6-[(3E,5E,7S)-5,7-dimethylnona-3,5-dien-1-ynyl]-2,4-dihydroxy-3-methylbenzaldehyde
  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

• 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.