(E)-1-[3,6-dimethoxy-2-(methoxymethoxy)-phenyl]-1-hydroxy-4-[2-(methoxymethoxy)-phenyl]-but-3-en-2-one | 914604-12-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-[3,6-dimethoxy-2-(methoxymethoxy)-phenyl]-1-hydroxy-4-[2-(methoxymethoxy)-phenyl]-but-3-en-2-one
• 英文别名: (E)-1-[3,6-dimethoxy-2-(methoxymethoxy)phenyl]-1-hydroxy-4-[2-(methoxymethoxy)phenyl]but-3-en-2-one
• CAS: 914604-12-9
• 化学式: C₂₂H₂₆O₈
• 分子量: 418.444
• InChiKey: LGDVMHCAWIMGAJ-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-1-[3,6-dimethoxy-2-(methoxymethoxy)-phenyl]-1-hydroxy-4-[2-(methoxymethoxy)-phenyl]-but-3-en-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 1-[3,6-dimethoxy-2-(methoxymethoxy)phenyl]-1-hydroxy-4-[2-(methoxymethoxy)phenyl]butan-2-one
  参考文献：
  名称：

  Synthesis of Bisbenzannulated SpiroketalsModel Studies for a Modular Approach to Rubromycins

  摘要：

  [GRAPHICS]A highly flexible synthesis of bisbenzannulated spiroketals is described with additions of lithiated methoxyallene to aryl aldehydes and Heck reactions as key steps. Subsequent hydrogenations and ketalizations afforded the desired spiroketals in good yields and with predominating trans-configuration. With model compound 30, already bearing the fully substituted naphthyl core of rubromycins, the ketalization proceeded efficiently providing the expected product 31 and the isopropoxy compound 32. Both products are advanced model compounds of heliquinomycin.

  DOI：

  10.1021/ol061932w
• 作为产物：
  描述：

  3,6-Dimethoxy-2-(methoxymethoxy)benzaldehyde 在 palladium diacetate 正丁基锂 、 potassium carbonate 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 (E)-1-[3,6-dimethoxy-2-(methoxymethoxy)-phenyl]-1-hydroxy-4-[2-(methoxymethoxy)-phenyl]-but-3-en-2-one
  参考文献：
  名称：

  Synthesis of Bisbenzannulated SpiroketalsModel Studies for a Modular Approach to Rubromycins

  摘要：

  [GRAPHICS]A highly flexible synthesis of bisbenzannulated spiroketals is described with additions of lithiated methoxyallene to aryl aldehydes and Heck reactions as key steps. Subsequent hydrogenations and ketalizations afforded the desired spiroketals in good yields and with predominating trans-configuration. With model compound 30, already bearing the fully substituted naphthyl core of rubromycins, the ketalization proceeded efficiently providing the expected product 31 and the isopropoxy compound 32. Both products are advanced model compounds of heliquinomycin.

  DOI：

  10.1021/ol061932w

文献信息

• Synthesis of Bisbenzannulated SpiroketalsModel Studies for a Modular Approach to Rubromycins
  作者：Sebastian Sörgel、Cengiz Azap、Hans-Ulrich Reissig

  DOI：10.1021/ol061932w

  日期：2006.10.1

  [GRAPHICS]A highly flexible synthesis of bisbenzannulated spiroketals is described with additions of lithiated methoxyallene to aryl aldehydes and Heck reactions as key steps. Subsequent hydrogenations and ketalizations afforded the desired spiroketals in good yields and with predominating trans-configuration. With model compound 30, already bearing the fully substituted naphthyl core of rubromycins, the ketalization proceeded efficiently providing the expected product 31 and the isopropoxy compound 32. Both products are advanced model compounds of heliquinomycin.