7-Ethynyl-6,6,8-trimethyl-1,4-dioxaspiro[4.5]decan-7-ol | 153786-92-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-Ethynyl-6,6,8-trimethyl-1,4-dioxaspiro[4.5]decan-7-ol
• CAS: 153786-92-6
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: ZEKGGONSYWQONZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-Ethynyl-6,6,8-trimethyl-1,4-dioxaspiro[4.5]decan-7-ol 在 palladium diacetate 、 氢氧化钾 、 对甲苯磺酸 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 红铝 、 lithium iodide 、 三氯氧磷 、 原甲酸三甲酯 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[(Z)-2-[2-(iodomethyl)-4,6-dimethoxyphenyl]ethenyl]-2,2,4-trimethylcyclohex-3-en-1-one
  参考文献：
  名称：

  An AC → ABC approach to taxol involving B-ring closure at C-1–C-2

  摘要：

  The treatment of keto aldehyde 13 with low-valent Ti results in a stereoselective intramolecular pinacol coupling that produces taxane synthesis intermediate 14.

  DOI：

  10.1016/s0040-4039(00)61582-4
• 作为产物：
  描述：

  乙炔锂乙二胺配合物 、 3,3-(ethylenedioxy)-2,2,6-trimethyl-1-cyclohexanone 以 四氢呋喃 为溶剂， 反应 48.0h， 以87%的产率得到7-Ethynyl-6,6,8-trimethyl-1,4-dioxaspiro[4.5]decan-7-ol
  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