10,20-Dimethyl-1,11-dioxacycloicosane-2,12-dione | 83637-45-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 10,20-Dimethyl-1,11-dioxacycloicosane-2,12-dione
• CAS: 83637-45-0
• 化学式: C₂₀H₃₆O₄
• 分子量: 340.503
• InChiKey: CWKHFDLIWTWEEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  9-癸烯酸 在 氢溴酸 、 甲基三辛基氯化铵 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.75h， 生成 10,20-Dimethyl-1,11-dioxacycloicosane-2,12-dione
  参考文献：
  名称：

  Cyclization of 9-substituted decanoic acid derivatives to 9-decanolide and 9-decanolactam

  摘要：

  Several standard and some novel cyclization reactions have been applied to 9-substituted decanoic acids to establish which are the optimum procedrues for lactonization and lactamization at 80-degrees-C under identical high-dilution conditions. The methods of Galli-Mandolini and Kellogg (cyclization of 9-bromodecanoate ion), Gerlach (cyclization of S-2-pyridyl 9-hydroxydecanethioate in the presence of AgClO4), and Yamaguchi (activation of the carboxyl group as a mixed with anhydride) in the presence of an excess of DMAP appear to be the most useful for the preparation of the 10-membered lactone, phoracantolide I, under these conditions. Analogously, treatment of S-2-pyridyl 9-azidodecanethioate with Sn(SePh)3-afforded the best yield of the 10-membered lactam. The mixed anhydrides RCOOCOAr (Ar = 2,4,6-trichlorophenyl) are more reactive than thioesters RCOSPy (Py = 2-pyridyl) with benzyl alcohol or benzylamine; it is confirmed that the addition of DMAP activates the reaction of alcohols with mixed anhydrides much more than with pyridyl thioesters, while the addition of Ag+ strongly activates RCOSPy in relation to either RCOOCOAr or RCOOSO2Mes.

  DOI：

  10.1021/jo00017a027

文献信息

• (±)-Phoracantholid I via the caesium carbonate-promoted ring closures of the methanesulphonate of 9-hydroxydecanoic acid
  作者：Michel barbier

  DOI：10.1039/c39820000668

  日期：——

  (±)-Phoracantholid I, a product from the secretion of the longicorn Phoracantha synonyma, has been synthesised via the caesium carbonate treatment of the methanesulphonate of 9-hydroxydecanoic acid, prepared from the easily accessible 9-oxo-derivative.

  （±）-Phoracantholid I是长角兽Phoracantha同义词的分泌产物，它是通过碳酸铯对9-羟基癸酸的甲磺酸盐进行碳酸铯处理而合成的，所述9-羟基癸酸的甲磺酸盐是由易于获得的9-氧代衍生物制备的。