(E)-6-(1-ethoxy-3-methylbuta-1,3-dienyl)-2-methyl-3,4-dihydro-2H-pyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环化合物
• 英文名称: (E)-6-(1-ethoxy-3-methylbuta-1,3-dienyl)-2-methyl-3,4-dihydro-2H-pyran
• 英文别名: 6-[(1E)-1-ethoxy-3-methylbuta-1,3-dienyl]-2-methyl-3,4-dihydro-2H-pyran
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: MQLDZDIUEGUPJF-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-(1-ethoxy-3-methylbuta-1,3-dienyl)-2-methyl-3,4-dihydro-2H-pyran 在 Amberlyst 15 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到2,5,5-trimethyl-3,4,5,6-tetrahydro-2H-cyclopenta[b]pyran-7-one
  参考文献：
  名称：

  New Synthetic Approach to Cyclopenta-Fused Heterocycles Based upon a Mild Nazarov Reaction. 2. Further Studies on the Torquoselectivity

  摘要：

  Conjugated alkoxytrienes in which one of the double bonds is embedded in a heterocyclic moiety are obtained by the Pd-catalyzed coupling reaction of lactam- and lactone-derived vinyl triflates with alpha-alkoxydienylboronates. These compounds undergo a 4pi electrocyclization process (Nazarov reaction) under acidic conditions and afford cyclopenta-fused heterocycles in good yields. As a continuation of a previous study, the torquoselectivity of this Nazarov reaction has been investigated using 2-alkyl-substituted pyrrolidinone and 2- and 4-substituted delta-valerolactone derivatives. High or complete stereoselectivity has only been observed with the 2-alkyl-substituted heterocycles. Both steric and stereoelectronic effects could contribute to determining the stereoselection of the ring closure.

  DOI：

  10.1021/jo0489263
• 作为产物：
  描述：

  丁位己内酯 在 六甲基磷酰三胺 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (E)-6-(1-ethoxy-3-methylbuta-1,3-dienyl)-2-methyl-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  New Synthetic Approach to Cyclopenta-Fused Heterocycles Based upon a Mild Nazarov Reaction. 2. Further Studies on the Torquoselectivity

  摘要：

  Conjugated alkoxytrienes in which one of the double bonds is embedded in a heterocyclic moiety are obtained by the Pd-catalyzed coupling reaction of lactam- and lactone-derived vinyl triflates with alpha-alkoxydienylboronates. These compounds undergo a 4pi electrocyclization process (Nazarov reaction) under acidic conditions and afford cyclopenta-fused heterocycles in good yields. As a continuation of a previous study, the torquoselectivity of this Nazarov reaction has been investigated using 2-alkyl-substituted pyrrolidinone and 2- and 4-substituted delta-valerolactone derivatives. High or complete stereoselectivity has only been observed with the 2-alkyl-substituted heterocycles. Both steric and stereoelectronic effects could contribute to determining the stereoselection of the ring closure.

  DOI：

  10.1021/jo0489263

文献信息

• New Synthetic Approach to Cyclopenta-Fused Heterocycles Based upon a Mild Nazarov Reaction. 2. Further Studies on the Torquoselectivity
  作者：Cristina Prandi、Alessandro Ferrali、Antonio Guarna、Paolo Venturello、Ernesto G. Occhiato

  DOI：10.1021/jo0489263

  日期：2004.10.1

  Conjugated alkoxytrienes in which one of the double bonds is embedded in a heterocyclic moiety are obtained by the Pd-catalyzed coupling reaction of lactam- and lactone-derived vinyl triflates with alpha-alkoxydienylboronates. These compounds undergo a 4pi electrocyclization process (Nazarov reaction) under acidic conditions and afford cyclopenta-fused heterocycles in good yields. As a continuation of a previous study, the torquoselectivity of this Nazarov reaction has been investigated using 2-alkyl-substituted pyrrolidinone and 2- and 4-substituted delta-valerolactone derivatives. High or complete stereoselectivity has only been observed with the 2-alkyl-substituted heterocycles. Both steric and stereoelectronic effects could contribute to determining the stereoselection of the ring closure.