2-tert-Butyl-2-methyl-6-(4'-methyl-4'-pentenyl)-1,3-dioxin-4-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-tert-Butyl-2-methyl-6-(4'-methyl-4'-pentenyl)-1,3-dioxin-4-one
• 英文别名: 2-Tert-butyl-2-methyl-6-(4-methylpent-4-enyl)-1,3-dioxin-4-one
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: ZZOAHVSJHSFMEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-tert-Butyl-2-methyl-6-(4'-methyl-4'-pentenyl)-1,3-dioxin-4-one 以 丙酮 、 乙腈 为溶剂， 反应 0.5h， 生成 3α-tert-Butyl-6β-hydro-3β,8α-dimethyl-2,4-dioxa-5-oxotricyclo<5.4.0.0^1,8>undecane 、 3α-tert-Butyl-6α-hydro-3β,8β-dimethyl-2,4-dioxa-5-oxotricyclo<5.4.0.0^1,8>undecane
  参考文献：
  名称：

  Intramolecular Photoaddition of Alkenes to Chiral 1,3-Dioxin-4-ones: Evidence for Effect of Pyramidalization on the Facial Selectivity

  摘要：

  Intramolecular photoaddition of alkenes to chiral 1,3-dioxin -4-ones 5 present, for the first time, examples with high facial selectivity in which the addition proceeds preferentially from the less exposed side (b-side) under kinetic control conditions. This unprecedented facial selectivity cannot be explained only on the basis of steric effects; however, it is consistent with the direction of pyramidalizaton in structure 3. It can be concluded that the geometry of the pyramidalized C-beta in the triplet excited dioxinones plays an important role in defining the facial selectivity in this reaction. However, steric effect cannot be neglected in rationalizing the facial selectivity as found by comparing the facial selectivity obtained in the irradiation of the studied compounds.

  DOI：

  10.1021/jo00126a045
• 作为产物：
  描述：

  4-碘-2-甲基丁-1-烯 、 2-t-butyl-2,6-dimethyl-1,3-dioxin-4-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 环己烷 为溶剂， 生成 、 2-tert-Butyl-2-methyl-6-(4'-methyl-4'-pentenyl)-1,3-dioxin-4-one
  参考文献：
  名称：

  Intramolecular Photoaddition of Alkenes to Chiral 1,3-Dioxin-4-ones: Evidence for Effect of Pyramidalization on the Facial Selectivity

  摘要：

  Intramolecular photoaddition of alkenes to chiral 1,3-dioxin -4-ones 5 present, for the first time, examples with high facial selectivity in which the addition proceeds preferentially from the less exposed side (b-side) under kinetic control conditions. This unprecedented facial selectivity cannot be explained only on the basis of steric effects; however, it is consistent with the direction of pyramidalizaton in structure 3. It can be concluded that the geometry of the pyramidalized C-beta in the triplet excited dioxinones plays an important role in defining the facial selectivity in this reaction. However, steric effect cannot be neglected in rationalizing the facial selectivity as found by comparing the facial selectivity obtained in the irradiation of the studied compounds.

  DOI：

  10.1021/jo00126a045

文献信息

• Intramolecular Photoaddition of Alkenes to Chiral 1,3-Dioxin-4-ones: Evidence for Effect of Pyramidalization on the Facial Selectivity
  作者：Nizar Haddad、Zehavit Abramovich

  DOI：10.1021/jo00126a045

  日期：1995.10

  Intramolecular photoaddition of alkenes to chiral 1,3-dioxin -4-ones 5 present, for the first time, examples with high facial selectivity in which the addition proceeds preferentially from the less exposed side (b-side) under kinetic control conditions. This unprecedented facial selectivity cannot be explained only on the basis of steric effects; however, it is consistent with the direction of pyramidalizaton in structure 3. It can be concluded that the geometry of the pyramidalized C-beta in the triplet excited dioxinones plays an important role in defining the facial selectivity in this reaction. However, steric effect cannot be neglected in rationalizing the facial selectivity as found by comparing the facial selectivity obtained in the irradiation of the studied compounds.