methyl (2E,4E)-7-[(2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oxy]hepta-2,4-dienoate | 757231-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2E,4E)-7-[(2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oxy]hepta-2,4-dienoate
• CAS: 757231-66-6
• 化学式: C₁₃H₂₀N₂O₅
• 分子量: 284.312
• InChiKey: FEGSJMXBMKUNJH-SBIWHPGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  78.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2E,4E)-7-[(2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oxy]hepta-2,4-dienoate 以 甲苯 为溶剂， 反应 20.0h， 以86%的产率得到(3aR,6R,6aR)-6a-Methoxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Formal Intramolecular (4 + 1)-Cycloaddition of Dialkoxycarbenes: Control of the Stereoselectivity and a Mechanistic Portrait

  摘要：

  The stereoselective synthesis of 5-5, 6-5, and 7-5 fused O-heterocyclic compounds is reported. The key reaction is a formal intramolecular (4 + 1)-cycloaddition involving a dialkox-ycarbene and an electron-deficient diene where the stereo-selectivity is dependent on the length of the tether. An analysis of the stereochemical outcome of this reaction sheds light on its complex mechanistic picture. High-level calculations were used to support the proposed mechanistic portrait.

  DOI：

  10.1021/ja211927b
• 作为产物：
  描述：

  4-溴-2-丁烯酸甲酯 在 camphor-10-sulfonic acid 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.75h， 生成 methyl (2E,4E)-7-[(2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oxy]hepta-2,4-dienoate
  参考文献：
  名称：

  Inter- and Intramolecular [4 + 1]-Cycloadditions Between Electron-Poor Dienes and Electron-Rich Carbenes

  摘要：

  Inter- and intramolecular [4 + 1]-annulations between dialkoxy carbenes and electron-deficient dienes afford mono- or bicyclic products in moderate to good yield.

  DOI：

  10.1021/ja046344x

文献信息

• Formal Intramolecular (4 + 1)-Cycloaddition of Dialkoxycarbenes: Control of the Stereoselectivity and a Mechanistic Portrait
  作者：Francis Beaumier、Marianne Dupuis、Claude Spino、Claude Y. Legault

  DOI：10.1021/ja211927b

  日期：2012.4.4

  The stereoselective synthesis of 5-5, 6-5, and 7-5 fused O-heterocyclic compounds is reported. The key reaction is a formal intramolecular (4 + 1)-cycloaddition involving a dialkox-ycarbene and an electron-deficient diene where the stereo-selectivity is dependent on the length of the tether. An analysis of the stereochemical outcome of this reaction sheds light on its complex mechanistic picture. High-level calculations were used to support the proposed mechanistic portrait.
• Inter- and Intramolecular [4 + 1]-Cycloadditions Between Electron-Poor Dienes and Electron-Rich Carbenes
  作者：Claude Spino、Hadi Rezaei、Kristina Dupont-Gaudet、Francis Bélanger

  DOI：10.1021/ja046344x

  日期：2004.8.1

  Inter- and intramolecular [4 + 1]-annulations between dialkoxy carbenes and electron-deficient dienes afford mono- or bicyclic products in moderate to good yield.