(3R,4aS,8S,8aS)-8-(but-3-en-1-yl)-3,8a-dimethyltetrahydrobenzo[b][1,4]dioxine-2,6(3H,5H)-dione | 1240408-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (3R,4aS,8S,8aS)-8-(but-3-en-1-yl)-3,8a-dimethyltetrahydrobenzo[b][1,4]dioxine-2,6(3H,5H)-dione
• CAS: 1240408-64-3
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: VQVWCIOFTCWWLV-IHOMSZDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (3R,4aS,8aS)-3,8a-dimethyl-4a,8a-dihydrobenzo[b][1,4]dioxine-2,6(3H,5H)-dione 、 3-Butenylmagnesium bromide 在 copper(I) bromide dimethylsulfide complex 、 三甲基氯硅烷 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 1.5h， 以89%的产率得到(3R,4aS,8S,8aS)-8-(but-3-en-1-yl)-3,8a-dimethyltetrahydrobenzo[b][1,4]dioxine-2,6(3H,5H)-dione
  参考文献：
  名称：

  Dearomatization applications of I(III) reagents and some unusual reactivity amongst resorcinol derived cyclohexadienones

  摘要：

  The oxidative dearomatization of resorcinol derivatives, which are outfitted with a lactic acid derived chiral tether, and mitigated by hypervalent iodine derivatives of PhIO, affords stable chiral cyclohexadienones as useful building blocks for the construction of many highly functionalized chiral six and seven-membered ring systems. Herein, we report a multitude of remarkable and unexpected diastereoselective transformations stemming from these cyclohexadienone adducts. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.05.041