| 173044-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 173044-53-6
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: PRDPJSLKDQYBBY-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以57%的产率得到
  参考文献：
  名称：

  Taxane Synthesis through Intramolecular Pinacol Coupling at C-1−C-2. Construction and Oxidative Transformations of a C-Aromatic Taxane Diene

  摘要：

  A ten-linear-step construction of C-aromatic taxane diene 14 from ethyl isopropyl ketone, acryloyl chloride, and commercially available 8 is reported. This sequence concludes with an intramolecular pinacol coupling carried out on 13. 14 is oxidized by m-chloroperbenzoic acid and dimethyldioxirane to give 17 through intermediate epoxide 20 and by VO(acac)(2)-t-BuOOH and Mo(CO)(6)-t-BuOOH to give 13. 17 is converted efficiently into 22 upon treatment with Mo(CO)(6)-t-BuOOH, apparently through an unusual equilibration with isomeric 20, which is converted irreversibly to 22. While these oxidative transformations highlight some of the peculiar reactivity patterns characteristic of taxane-related structures, the formation of 14 through an intramolecular pinacol coupling that joins C-l and C-2 demonstrates the potential of this strategy for stereoselectively delivering advanced taxane synthesis intermediates.

  DOI：

  10.1021/jo951935e
• 作为产物：
  描述：

  2-iodo-3,5-dimethoxybenzyl acetate 在 palladium on barium sulfate 吡啶 、 manganese(IV) oxide 、 palladium diacetate 、 氢氧化钾 、 sodium tetrahydroborate 、 氢气 、 三乙胺 、 三苯基膦 、 三氯氧磷 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 水 、 苯 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 33.5h， 生成
  参考文献：
  名称：

  Taxane Synthesis through Intramolecular Pinacol Coupling at C-1−C-2. Construction and Oxidative Transformations of a C-Aromatic Taxane Diene

  摘要：

  A ten-linear-step construction of C-aromatic taxane diene 14 from ethyl isopropyl ketone, acryloyl chloride, and commercially available 8 is reported. This sequence concludes with an intramolecular pinacol coupling carried out on 13. 14 is oxidized by m-chloroperbenzoic acid and dimethyldioxirane to give 17 through intermediate epoxide 20 and by VO(acac)(2)-t-BuOOH and Mo(CO)(6)-t-BuOOH to give 13. 17 is converted efficiently into 22 upon treatment with Mo(CO)(6)-t-BuOOH, apparently through an unusual equilibration with isomeric 20, which is converted irreversibly to 22. While these oxidative transformations highlight some of the peculiar reactivity patterns characteristic of taxane-related structures, the formation of 14 through an intramolecular pinacol coupling that joins C-l and C-2 demonstrates the potential of this strategy for stereoselectively delivering advanced taxane synthesis intermediates.

  DOI：

  10.1021/jo951935e

文献信息

• Unusual oxidative transformations of a C-aromatic taxane diene and related structures
  作者：Charles S. Swindell、Madhavi C. Chander

  DOI：10.1016/0040-4039(94)88059-x

  日期：1994.8

  The interaction of 1 and related substances with MCPBA, dimethyldioxirane, VO(acach)(2)-t-BuOOH, and Mo(C0)(6)-t-BuOOH affords products with oxygenated A-rings and/or cleaved B-rings through novel oxidative processes.