(Z)-2-((5-iodopent-4-en-1-yl)oxy)-2-methoxy-5,5-dimethyl-2,5-dihydro-1,3,4-oxadiazole | 1369875-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-2-((5-iodopent-4-en-1-yl)oxy)-2-methoxy-5,5-dimethyl-2,5-dihydro-1,3,4-oxadiazole
• CAS: 1369875-63-7
• 化学式: C₁₀H₁₇IN₂O₃
• 分子量: 340.161
• InChiKey: APFLCEMJKQGKMT-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.41
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-((5-iodopent-4-en-1-yl)oxy)-2-methoxy-5,5-dimethyl-2,5-dihydro-1,3,4-oxadiazole 、 methyl (E)-3-(tributylstannyl)acrylate 在 双(乙腈)氯化钯(II) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以65%的产率得到
  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：

  (Z)-5-iodo-4-penten-1-ol 、 methyl-2,3-diaza-4-methyl-4-acetoxypent-2-enoate 在 lead(IV) tetraacetate 、 溶剂黄146 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以923 mg的产率得到(Z)-2-((5-iodopent-4-en-1-yl)oxy)-2-methoxy-5,5-dimethyl-2,5-dihydro-1,3,4-oxadiazole
  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