7-methyloxacyclo-9-undecyne-2,6-dione | 110797-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 7-methyloxacyclo-9-undecyne-2,6-dione
• 英文别名: 7-Methyl-1-oxacycloundec-9-yne-2,6-dione
• CAS: 110797-11-0
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: KYFIMMHNHSRTKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-methyloxacyclo-9-undecyne-2,6-dione 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.33h， 以72%的产率得到7,18-dimethyl-1,12-dioxacyclodocosa-9,20-diyne-2,6,13,17-tetraone
  参考文献：
  名称：

  Use of metal complexation in the synthesis of medium-ring acetylenic lactones

  摘要：

  The hexacarbonyldicobalt complexes of several appropriately designed acetylenic lactone precursors have been prepared, and lactones containing Co2(CO)6-complexed triple bonds in seven-, ten-, and eleven-membered rings obtained. The latter were best obtained through a retro-Dieckmann fragmentation of 2-(hydroxybutynyl) derivatives of 1,3-cyclohexanedione. Attempts to extend this reaction to cyclohexanones bearing other anion-stabilizing groups in the 2-position or to 1,3-cyclopentanediones were unsuccessful. Decomplexation afforded the metal-free 11-ring lactone, characterized crystallographically. Treatment of this system with basic reagents led to dimerization. In the case of the smaller rings, cyclization of the complexed acetylenic hydroxyacids under Mukaiyama conditions (2-chloro-N-methylpyridinium iodide, CH2Cl2, reflux) succeeded in modest yields.

  DOI：

  10.1016/0022-328x(92)83338-i
• 作为产物：
  描述：

  2-(4-hydroxy-2-butynyl)-2-methylcyclohexane-1,3-dione 在 dicobalt octacarbonyl 、 ammonium cerium(IV) nitrate 、 sodium hydride 作用下， 生成 10-Hydroxy-6-methyl-5-oxo-dec-8-ynoic acid 、 7-methyloxacyclo-9-undecyne-2,6-dione
  参考文献：
  名称：

  Use of metal complexation in the synthesis of medium-ring acetylenic lactones

  摘要：

  The hexacarbonyldicobalt complexes of several appropriately designed acetylenic lactone precursors have been prepared, and lactones containing Co2(CO)6-complexed triple bonds in seven-, ten-, and eleven-membered rings obtained. The latter were best obtained through a retro-Dieckmann fragmentation of 2-(hydroxybutynyl) derivatives of 1,3-cyclohexanedione. Attempts to extend this reaction to cyclohexanones bearing other anion-stabilizing groups in the 2-position or to 1,3-cyclopentanediones were unsuccessful. Decomplexation afforded the metal-free 11-ring lactone, characterized crystallographically. Treatment of this system with basic reagents led to dimerization. In the case of the smaller rings, cyclization of the complexed acetylenic hydroxyacids under Mukaiyama conditions (2-chloro-N-methylpyridinium iodide, CH2Cl2, reflux) succeeded in modest yields.

  DOI：

  10.1016/0022-328x(92)83338-i

文献信息

• Use of metal complexation in the synthesis of medium-ring acetylenic lactones
  作者：Samir D. Najdi、Marilyn M. Olmstead、Neil E. Schore

  DOI：10.1016/0022-328x(92)83338-i

  日期：1992.7

  The hexacarbonyldicobalt complexes of several appropriately designed acetylenic lactone precursors have been prepared, and lactones containing Co2(CO)6-complexed triple bonds in seven-, ten-, and eleven-membered rings obtained. The latter were best obtained through a retro-Dieckmann fragmentation of 2-(hydroxybutynyl) derivatives of 1,3-cyclohexanedione. Attempts to extend this reaction to cyclohexanones bearing other anion-stabilizing groups in the 2-position or to 1,3-cyclopentanediones were unsuccessful. Decomplexation afforded the metal-free 11-ring lactone, characterized crystallographically. Treatment of this system with basic reagents led to dimerization. In the case of the smaller rings, cyclization of the complexed acetylenic hydroxyacids under Mukaiyama conditions (2-chloro-N-methylpyridinium iodide, CH2Cl2, reflux) succeeded in modest yields.