(6R)-4-((2R)-2-methylbutanoyl)-6-hydroxy-3,5-dimethoxy-2,6-dimethylcyclohexa-2,4-dienone | 287102-35-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6R)-4-((2R)-2-methylbutanoyl)-6-hydroxy-3,5-dimethoxy-2,6-dimethylcyclohexa-2,4-dienone
• 英文别名: wasabidienone B1；(6R)-6-hydroxy-3,5-dimethoxy-2,6-dimethyl-4-[(2R)-2-methylbutanoyl]cyclohexa-2,4-dien-1-one
• CAS: 287102-35-6
• 化学式: C₁₅H₂₂O₅
• 分子量: 282.337
• InChiKey: XAKJHYHFOWVGDO-GLEZIHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6R)-4-((2R)-2-methylbutanoyl)-6-hydroxy-3,5-dimethoxy-2,6-dimethylcyclohexa-2,4-dienone 以 苯 为溶剂， 反应 20.0h， 以33%的产率得到(5S^*)-5-acetyl-3,5-dimethoxy-2-methyl-(4R^*)-4-<(2R^*)-2-methylbutanoyl>-2-cyclopenten-1-one
  参考文献：
  名称：

  Isolation and Structure of a New Natural Cyclopentenone Derivative from Potato Culture Solution ofPhoma wasabiaeYokogi

  摘要：

  通过光谱和单晶 X 射线衍射分析，从马铃薯瘤培养液中分离出一种新的天然环戊烯酮衍生物，并确定其结构为 (5S*)-5- 乙酰基-3,5-二甲氧基-2-甲基-(4R*)-4-[(2R*)-2-甲基丁酰基]-2-环戊烯-1-酮。

  DOI：

  10.1246/cl.1988.1535
• 作为产物：
  描述：

  (R)-1-(4-hydroxy-2,6-dimethoxy-3,5-dimethylphenyl)-2-methylbutan-1-one 在 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 (6S)-4-((2R)-2-methylbutanoyl)-6-hydroxy-3,5-dimethoxy-2,6-dimethylcyclohexa-2,4-dienone 、 (6R)-4-((2R)-2-methylbutanoyl)-6-hydroxy-3,5-dimethoxy-2,6-dimethylcyclohexa-2,4-dienone
  参考文献：
  名称：

  Total Synthesis of Wasabidienones B₁ and B₀ via SIBX-Mediated Hydroxylative Phenol Dearomatization

  摘要：

  The first total synthesis of the natural nondimerizing o-quinol (+)-wasabidienone B-1 was achieved from commercially available 1,3,5-trimethoxybenzene. The key dearomatizing transformation was efficiently accomplished via a hydroxylative phenol dearomatization reaction using the stabilized lambda(5)-iodane reagent IBX (SIBX). (+)-Wasabidienone B-1 was then converted into its congener (-)-wasabidienone B-0 via an improved thermally induced ring-contracting isomerization reaction.

  DOI：

  10.1021/ol802183p

文献信息

• Isolation and Structure of a New Natural Cyclopentenone Derivative from Potato Culture Solution of<i>Phoma wasabiae</i>Yokogi
  作者：Osamu Soga、Hidetoshi Iwamoto、Akio Takuwa、Tamayo Takata、Yuko Tsugiyama、Kensaku Hamada、Takaji Fujiwara、Mitsuru Nakayama

  DOI：10.1246/cl.1988.1535

  日期：1988.9.5

  A new natural cyclopentenone derivative has been isolated from the potato culture solution of Phoma wasabiae, and its structure was determined to be (5S*)-5-acetyl-3,5-dimethoxy-2-methyl-(4R*)-4-[(2R*)-2-methylbutanoyl]-2-cyclopenten-1-one by spectroscopic and single crystal X-ray diffraction analyses.

  通过光谱和单晶 X 射线衍射分析，从马铃薯瘤培养液中分离出一种新的天然环戊烯酮衍生物，并确定其结构为 (5S*)-5- 乙酰基-3,5-二甲氧基-2-甲基-(4R*)-4-[(2R*)-2-甲基丁酰基]-2-环戊烯-1-酮。
• Total Synthesis of Wasabidienones B₁ and B₀ via SIBX-Mediated Hydroxylative Phenol Dearomatization
  作者：Laurent Pouységu、Mélanie Marguerit、Julien Gagnepain、Gildas Lyvinec、Andrew J. Eatherton、Stéphane Quideau

  DOI：10.1021/ol802183p

  日期：2008.11.20

  The first total synthesis of the natural nondimerizing o-quinol (+)-wasabidienone B-1 was achieved from commercially available 1,3,5-trimethoxybenzene. The key dearomatizing transformation was efficiently accomplished via a hydroxylative phenol dearomatization reaction using the stabilized lambda(5)-iodane reagent IBX (SIBX). (+)-Wasabidienone B-1 was then converted into its congener (-)-wasabidienone B-0 via an improved thermally induced ring-contracting isomerization reaction.