(2E,4E)-8-[(2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oxy]octa-2,4-dienenitrile | 1369873-92-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E,4E)-8-[(2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oxy]octa-2,4-dienenitrile
• CAS: 1369873-92-6
• 化学式: C₁₃H₁₉N₃O₃
• 分子量: 265.312
• InChiKey: YQYCRILLYATQOU-DVBIZMGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E,4E)-8-[(2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oxy]octa-2,4-dienenitrile 在 水 作用下， 以 甲苯 为溶剂， 反应 22.0h， 生成 (4E,6E)-7-cyanohepta-4,6-dien-1-yl formate
  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：

  methyl-2,3-diaza-4-methyl-4-acetoxypent-2-enoate 在 草酰氯 、 lead(IV) tetraacetate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium hydroxide 、 lithium hexamethyldisilazane 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 37.01h， 生成 (2E,4E)-8-[(2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oxy]octa-2,4-dienenitrile
  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

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.