(S)-1-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-6-(triisopropylsilyloxy)heptane-2,4-dione | 1192264-05-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-6-(triisopropylsilyloxy)heptane-2,4-dione
• 英文别名: (6S)-1-(2,2-dimethyl-6-oxo-1,3-dioxin-4-yl)-6-tri(propan-2-yl)silyloxyheptane-2,4-dione
• CAS: 1192264-05-3
• 化学式: C₂₂H₃₈O₆Si
• 分子量: 426.626
• InChiKey: JIJVROSZVYIGLO-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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)-1-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-6-(triisopropylsilyloxy)heptane-2,4-dione 在 caesium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 22.0h， 生成 (S)-methyl 2,4-dihydroxy-6-(2-(tri-isopropylsilyloxy)propyl)benzoate
  参考文献：
  名称：

  Biomimetic Total Synthesis of Angelicoin A and B via a Palladium-Catalyzed Decarboxylative Prenylation-Aromatization Sequence

  摘要：

  Five-step total syntheses of angelicoin A and B from 2,2,6-trimethyl-4-dioxinone are reported using late stage biomimetic aromatization reactions via diketo-dioxinones as intermediates. In addition, with angelicoin A, this aromatization was coupled with a palladium-catalyzed decarboxylative prenylation in a one-pot sequence as the key step.

  DOI：

  10.1021/ol202320m
• 作为产物：
  描述：

  (5S)-allyl 2-(2-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)acetyl)-3-oxo-5-(triisopropylsilyloxy)hexanoate 在 吗啉 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 0.92h， 生成 (S)-1-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-6-(triisopropylsilyloxy)heptane-2,4-dione
  参考文献：
  名称：

  Biomimetic Total Synthesis of Angelicoin A and B via a Palladium-Catalyzed Decarboxylative Prenylation-Aromatization Sequence

  摘要：

  Five-step total syntheses of angelicoin A and B from 2,2,6-trimethyl-4-dioxinone are reported using late stage biomimetic aromatization reactions via diketo-dioxinones as intermediates. In addition, with angelicoin A, this aromatization was coupled with a palladium-catalyzed decarboxylative prenylation in a one-pot sequence as the key step.

  DOI：

  10.1021/ol202320m

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.
• Biomimetic Total Synthesis of Angelicoin A and B via a Palladium-Catalyzed Decarboxylative Prenylation-Aromatization Sequence
  作者：Katie Anderson、Frederick Calo、Toni Pfaffeneder、Andrew J. P. White、Anthony G. M. Barrett

  DOI：10.1021/ol202320m

  日期：2011.11.4

  Five-step total syntheses of angelicoin A and B from 2,2,6-trimethyl-4-dioxinone are reported using late stage biomimetic aromatization reactions via diketo-dioxinones as intermediates. In addition, with angelicoin A, this aromatization was coupled with a palladium-catalyzed decarboxylative prenylation in a one-pot sequence as the key step.