(6S)-1-(2-methyl-6-oxo-2-phenyl-1,3-dioxin-4-yl)-6-tri(propan-2-yl)silyloxyheptane-2,4-dione | 1192264-11-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6S)-1-(2-methyl-6-oxo-2-phenyl-1,3-dioxin-4-yl)-6-tri(propan-2-yl)silyloxyheptane-2,4-dione
• CAS: 1192264-11-1
• 化学式: C₂₇H₄₀O₆Si
• 分子量: 488.697
• InChiKey: NDNIHYSXGKQVSL-LWAJAQLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2,4,6-trimethylbenzyl 2,4-dihydroxy-6-(2-hydroxypropyl)benzoate 、 (6S)-1-(2-methyl-6-oxo-2-phenyl-1,3-dioxin-4-yl)-6-tri(propan-2-yl)silyloxyheptane-2,4-dione 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Tuning Diketodioxinone Reactivity: Biomimetic Synthesis of the Resorcylate Antibiotic Fungal Metabolites ent-W1278A, -B, and -C, Using Iterative Aromatization Reactions

  摘要：

  The onset temperature of the retro-Diels-Alder reactions of diketo-1,3-dioxin-2-ones to generate alpha,gamma,epsilon-triketo-ketenes was found to be significantly reduced with 2-phenyl substitution. These ketenes, generated at 78 degrees C, were trapped with alcohols to provide resorcylate esters following aromatization by sequential reaction with cesium acetate and trifluoroacetic acid. The methodology was applied iteratively to the total synthesis of the resorcylate antibiotics W1278A, -B, and -C. It is noteworthy that in this process the linking of the monomer units occurs during construction of the aromatic ring.

  DOI：

  10.1021/jo9015858
• 作为产物：
  描述：

  2-methyl-6-(2-oxopropyl)-2-phenyl-4H-1,3-dioxin-4-one 、 (S)-N-methoxy-N-methyl-3-triisopropylsilyloxybutyramide 在 正丁基锂 、 二异丙胺 、 盐酸 、 氯化铵 作用下， 以 四氢呋喃 、 hexanes 、 水 为溶剂， 反应 2.0h， 以63%的产率得到(6S)-1-(2-methyl-6-oxo-2-phenyl-1,3-dioxin-4-yl)-6-tri(propan-2-yl)silyloxyheptane-2,4-dione
  参考文献：
  名称：

  Tuning Diketodioxinone Reactivity: Biomimetic Synthesis of the Resorcylate Antibiotic Fungal Metabolites ent-W1278A, -B, and -C, Using Iterative Aromatization Reactions

  摘要：

  The onset temperature of the retro-Diels-Alder reactions of diketo-1,3-dioxin-2-ones to generate alpha,gamma,epsilon-triketo-ketenes was found to be significantly reduced with 2-phenyl substitution. These ketenes, generated at 78 degrees C, were trapped with alcohols to provide resorcylate esters following aromatization by sequential reaction with cesium acetate and trifluoroacetic acid. The methodology was applied iteratively to the total synthesis of the resorcylate antibiotics W1278A, -B, and -C. It is noteworthy that in this process the linking of the monomer units occurs during construction of the aromatic ring.

  DOI：

  10.1021/jo9015858

文献信息

• Tuning Diketodioxinone Reactivity: Biomimetic Synthesis of the Resorcylate Antibiotic Fungal Metabolites <i>ent</i>-W1278A, -B, and -C, Using Iterative Aromatization Reactions
  作者：Ismael Navarro、Christoph Pöverlein、Gerhard Schlingmann、Anthony G. M. Barrett

  DOI：10.1021/jo9015858

  日期：2009.11.6

  The onset temperature of the retro-Diels-Alder reactions of diketo-1,3-dioxin-2-ones to generate alpha,gamma,epsilon-triketo-ketenes was found to be significantly reduced with 2-phenyl substitution. These ketenes, generated at 78 degrees C, were trapped with alcohols to provide resorcylate esters following aromatization by sequential reaction with cesium acetate and trifluoroacetic acid. The methodology was applied iteratively to the total synthesis of the resorcylate antibiotics W1278A, -B, and -C. It is noteworthy that in this process the linking of the monomer units occurs during construction of the aromatic ring.