2-iodo-1,8-bis(methoxymethoxy)anthracene | 134112-16-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-iodo-1,8-bis(methoxymethoxy)anthracene
• 英文别名: 1,8-Bis(methoxymethoxy)-2-iodoanthracene
• CAS: 134112-16-6
• 化学式: C₁₈H₁₇IO₄
• 分子量: 424.235
• InChiKey: DFGHHBZMWKLRMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-iodo-1,8-bis(methoxymethoxy)anthracene 在 bis-triphenylphosphine-palladium(II) chloride 、 正丁基锂 、 四甲基乙二胺 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 生成 2-carbomethoxy-1,8-bis(methoxymethoxy)-7-phenylanthracene
  参考文献：
  名称：

  C-Glycosylanthraquinone synthesis: total synthesis of vineomycinone B2 methyl ester

  摘要：

  A synthesis of substituted anthraquinones has been developed. Commercially available anthrarufin and 1,8-dihydroxyanthraquinone were converted to the corresponding (methoxymethoxy)anthracenes. Directed metalation followed by stannylation produced stable intermediates that were either alkylated, arylated, acylated, and/or C-glycosylated. The value of this new methodology was demonstrated by the triply convergent total synthesis of vineomycinone B2 methyl ester, a representative C-glycosylanthraquinone antibiotic.

  DOI：

  10.1021/ja00015a035
• 作为产物：
  描述：

  2-(tributylstannyl)-1,8-bis(methoxymethoxy)anthracene 在 碘 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到2-iodo-1,8-bis(methoxymethoxy)anthracene
  参考文献：
  名称：

  C-Glycosylanthraquinone synthesis: total synthesis of vineomycinone B2 methyl ester

  摘要：

  A synthesis of substituted anthraquinones has been developed. Commercially available anthrarufin and 1,8-dihydroxyanthraquinone were converted to the corresponding (methoxymethoxy)anthracenes. Directed metalation followed by stannylation produced stable intermediates that were either alkylated, arylated, acylated, and/or C-glycosylated. The value of this new methodology was demonstrated by the triply convergent total synthesis of vineomycinone B2 methyl ester, a representative C-glycosylanthraquinone antibiotic.

  DOI：

  10.1021/ja00015a035

文献信息

• Synthesis and Bioactivities of Naturally Occurring Anthraquinones: Isochrysophanol, Isozyganein, ω-Hydroxyisochrysophanol and Morindaparvin
  作者：Javed H. Zaidi、Fazal Naeem、Rashid Iqbal、Mohammed Iqbal Choudhary、Khalid Mohammed Khan、Shahnaz Perveen、Syed T. Ali Shah、Safdar Hayat、Wolfgang Voelter

  DOI：10.1515/znb-2001-0717

  日期：2001.7.1

  Isochrysophanol, isozyganein, ω-hydroxyisochrysophanol, and morindaparvin are naturally occurring substituted anthraquinones. We report the synthesis of these compounds as well as selected biological activities.

  异黄酚、isozyganein、ω-羟基异黄酚和morindaparvin 是天然存在的取代蒽醌。我们报告了这些化合物的合成以及选定的生物活性。