(S)-2,4,6-trimethylbenzyl 2,4-dihydroxy-6-(2-hydroxypropyl)benzoate | 1192264-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2,4,6-trimethylbenzyl 2,4-dihydroxy-6-(2-hydroxypropyl)benzoate
• 英文别名: (2,4,6-trimethylphenyl)methyl 2,4-dihydroxy-6-[(2S)-2-hydroxypropyl]benzoate
• CAS: 1192264-07-5
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: XIDKGMOJIVMHCJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2,4,6-trimethylbenzyl 2,4-dihydroxy-6-(2-hydroxypropyl)benzoate 以 甲苯 为溶剂， 反应 2.0h， 以100%的产率得到(S)-6-hydroxymellein
  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：

  (S)-2,4,6-trimethylbenzyl 2,4-dihydroxy-6-(2-(triisopropylsilyloxy)propyl)benzoate 在 六氟合硅酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.75h， 以92%的产率得到(S)-2,4,6-trimethylbenzyl 2,4-dihydroxy-6-(2-hydroxypropyl)benzoate
  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