6-Hex-5-enyl-2,3-dihydropyran-4-one | 153000-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-Hex-5-enyl-2,3-dihydropyran-4-one
• CAS: 153000-36-3
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: OIJFKPLJTYQFTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Hex-5-enyl-2,3-dihydropyran-4-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.58h， 生成 2-(5-Hydroxy-3-oxopentyl)cyclohexan-1-one
  参考文献：
  名称：

  Studies on the intramolecular [2+2] photocycloaddition of dihydro-4-pyrones

  摘要：

  Dihydropyrones 3 shown to undergo intramolecular photocycloaddition in high regioselectivity and good yields. The oxygen-heteroatom plays an important role in the regioselectivity of this reaction and in the subsequent fragmentations. Two possible approaches of the olefin to the cyclic enone have been described.

  DOI：

  10.1016/s0040-4039(00)61747-1
• 作为产物：
  描述：

  6-碘-1-己烯 在 叔丁基锂 、 草酸 、 silica gel 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 6-Hex-5-enyl-2,3-dihydropyran-4-one
  参考文献：
  名称：

  Studies on the intramolecular [2+2] photocycloaddition of dihydro-4-pyrones

  摘要：

  Dihydropyrones 3 shown to undergo intramolecular photocycloaddition in high regioselectivity and good yields. The oxygen-heteroatom plays an important role in the regioselectivity of this reaction and in the subsequent fragmentations. Two possible approaches of the olefin to the cyclic enone have been described.

  DOI：

  10.1016/s0040-4039(00)61747-1

文献信息

• Synthesis of substituted phenols Via photoaddition-fragmentation-aromatic annelation sequence
  作者：Nizar Haddad、Irina Kuzmenkov

  DOI：10.1016/0040-4039(96)00083-4

  日期：1996.3

  Intramolecular photocycloaddition reaction of dihyro-4-pyrones to alkenes (1), followed by fragmentation then subsequent aromatic annelation, carried out by two alternative methods, has been performed efficiently. The sequence provides a convenient method for the construction of substituted phenols fused to aliphatic ring (4).

  二氢-4-吡喃酮与烯烃的分子内光环加成反应（1），然后进行断裂，然后通过两种替代方法进行的随后的芳族芳构化反应已得到有效执行。该序列为构建与脂族环（4）稠合的取代酚提供了便利的方法。
• Studies on the intramolecular [2+2] photocycloaddition of dihydro-4-pyrones
  作者：Nizar Haddad、Irina Kusmenkov

  DOI：10.1016/s0040-4039(00)61747-1

  日期：1993.9

  Dihydropyrones 3 shown to undergo intramolecular photocycloaddition in high regioselectivity and good yields. The oxygen-heteroatom plays an important role in the regioselectivity of this reaction and in the subsequent fragmentations. Two possible approaches of the olefin to the cyclic enone have been described.