(1R,2R,4S)-3,3-Dimethoxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester | 142968-11-4

• 分子结构分类: 有机化合物
• 英文名称: (1R,2R,4S)-3,3-Dimethoxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
• CAS: 142968-11-4
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: ZRZVJSYEZZTGOW-CSMHCCOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S)-3,3-Dimethoxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 在 Nafion-501 (H+ form) 作用下， 以 丙酮 为溶剂， 反应 96.0h， 以68%的产率得到(±)-3-endo-(methoxycarbonyl)-7-oxabicyclo[2.2.1]hepta-5-en-2-one
  参考文献：
  名称：

  Diels-Alder reaction of furan with methyl 3-bromopropiolate: a route to methyl 3-oxo-7-oxabicyclo[2.2.1]hept-5-en-2-carboxylate

  摘要：

  The two epimers of methyl 3-oxo-7-oxabicyclo[2.2.1]hept-5-en-2-carboxylate have been prepared from furan and methyl 3-bromopropiolate as a methoxycarbonylketene equivalent. The final step required hydrolysis of acetals by Nafion-H.

  DOI：

  10.1016/s0040-4039(00)79574-8
• 作为产物：
  描述：

  sodium methylate 、 methyl 3-bromo-7-oxabicyclo[2.2.1]hepta-2,5-diene-2-carboxylate 以 甲醇 为溶剂， 生成 (1R,2R,4S)-3,3-Dimethoxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 、 (1S,2R,4R)-3,3-Dimethoxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Diels-Alder reaction of furan with methyl 3-bromopropiolate: a route to methyl 3-oxo-7-oxabicyclo[2.2.1]hept-5-en-2-carboxylate

  摘要：

  The two epimers of methyl 3-oxo-7-oxabicyclo[2.2.1]hept-5-en-2-carboxylate have been prepared from furan and methyl 3-bromopropiolate as a methoxycarbonylketene equivalent. The final step required hydrolysis of acetals by Nafion-H.

  DOI：

  10.1016/s0040-4039(00)79574-8