dimethyl 2-ethoxy-6,6-dimethoxy-5-oxa-bicyclo[2.1.1]hexane-1,4-dicarboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 2-ethoxy-6,6-dimethoxy-5-oxa-bicyclo[2.1.1]hexane-1,4-dicarboxylate
• 英文别名: dimethyl (1R,2R,4S)-2-ethoxy-6,6-dimethoxy-5-oxabicyclo[2.1.1]hexane-1,4-dicarboxylate
• 化学式: C₁₃H₂₀O₈
• 分子量: 304.297
• InChiKey: DZHDLSTWMGABSF-FXAINCCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 (1S,4R,5R)-1,4-Dibromo-5-ethoxy-7,7-dimethoxy-bicyclo[2.2.1]heptane-2,3-dione 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 33.0h， 以63%的产率得到dimethyl 2-ethoxy-6,6-dimethoxy-5-oxa-bicyclo[2.1.1]hexane-1,4-dicarboxylate
  参考文献：
  名称：

  Synthesis of a Novel, Highly Symmetric Bis-Oxa-Bridged Compound

  摘要：

  A highly oxygenated, novel pentacyclic bis-oxa-bridged compound 8 was synthesized with remarkable efficiency starting from readily available tetrachloro-5,5-dimethoxyclopentadiene and 1,4-cyclohexadiene in three steps. The ruthenium-catalyzed oxidation of 2:1 bis-adduct 1 followed by a one-pot transformation of the resulting bis-alpha-diketone 3 furnished (after esterification) the title compound in an overall yield of 29.1%. The versatility of this simple method was further demonstrated with other norbornyl alpha-diketones to obtain the corresponding strained oxa-bridged derivatives.

  DOI：

  10.1021/ja017371f

文献信息

• Synthesis of a Novel, Highly Symmetric Bis-Oxa-Bridged Compound
  作者：Faiz Ahmed Khan、Jyotirmayee Dash

  DOI：10.1021/ja017371f

  日期：2002.3.1

  A highly oxygenated, novel pentacyclic bis-oxa-bridged compound 8 was synthesized with remarkable efficiency starting from readily available tetrachloro-5,5-dimethoxyclopentadiene and 1,4-cyclohexadiene in three steps. The ruthenium-catalyzed oxidation of 2:1 bis-adduct 1 followed by a one-pot transformation of the resulting bis-alpha-diketone 3 furnished (after esterification) the title compound in an overall yield of 29.1%. The versatility of this simple method was further demonstrated with other norbornyl alpha-diketones to obtain the corresponding strained oxa-bridged derivatives.