6-Methyl-6-(3-oxo-butyl)-1,4-dioxa-spiro[4.5]decan-7-one | 129156-19-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Methyl-6-(3-oxo-butyl)-1,4-dioxa-spiro[4.5]decan-7-one
• 英文别名: 6-Methyl-6-(3-oxobutyl)-1,4-dioxaspiro[4.5]decan-7-one
• CAS: 129156-19-0
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: POPQBSUBNJBVEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Methyl-6-(3-oxo-butyl)-1,4-dioxa-spiro[4.5]decan-7-one 在 titanium(III) chloride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 30.0h， 以75%的产率得到2',3',3a',5',6',7'-hexahydro-1',3'a-dimethylspiro<1,3-dioxolane-2,4'-<4H>indene>
  参考文献：
  名称：

  New low-valent titanium reagents for dicarbonyl coupling and their use in a general method of annulation

  摘要：

  New low-valent titanium reagents have been prepared by reducing TiCl3 (1 mol) with C8K (2 mol) or by reducing TiCl4 (1 mol) with Na-naphthalene (2.75 mol). Ketones carrying a chain that incorporates a suitably placed oxo function (aldehyde or ketone) undergo intramolecular dicarbonyl coupling to produce a bicyclic compound when treated with an excess (16-17 mol of titanium halide per mol of dicarbonyl compound) of one of these reagents. The procedure works well even for highly oxygenated substrates and constitutes a general method of annulation. Other reducing agents besides C8K or Na-naphthalene are suitable, and a brief examination of Na(Hg) and Na-K alloy was made. The C8K/TiCl3 system was also used to convert a cis-1,2-diol into the corresponding olefin.

  DOI：

  10.1021/jo00022a042