methyl 2-[(2R,4aR,6S,9aS)-2-(4-methoxyphenyl)-7-oxo-4a,8,9,9a-tetrahydro-4H-[1,3]dioxino[5,4-b]oxepin-6-yl]acetate | 943732-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 2-[(2R,4aR,6S,9aS)-2-(4-methoxyphenyl)-7-oxo-4a,8,9,9a-tetrahydro-4H-[1,3]dioxino[5,4-b]oxepin-6-yl]acetate
• CAS: 943732-29-4
• 化学式: C₁₈H₂₂O₇
• 分子量: 350.368
• InChiKey: CGLOEIJBHZSZQE-LISAXSMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2R,4aR,6S,9aS)-2-(4-methoxyphenyl)-7-oxo-4a,8,9,9a-tetrahydro-4H-[1,3]dioxino[5,4-b]oxepin-6-yl]acetate 、 三甲基氯硅烷 在 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  A Concise Route to Two Distinct E-Ring Structures of Ciguatoxins

  摘要：

  Ciguatoxins, the causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers, and known to have more than 20 structurally distinct congeners. In this paper, we describe a new concise synthesis of the two E-ring structures, of different ring sizes, found in ciguatoxins. From the common oxepane intermediate, the seven-membered E-ring was prepared in three steps, and the eight-membered E-ring was synthesized in seven steps using ring expansion and olefin isomerization as key reactions.

  DOI：

  10.3987/com-06-s(k)16
• 作为产物：
  描述：

  methyl (E)-3-[[(2R,4S,5R)-2-(4-methoxyphenyl)-4-(3-oxo-3-phenylselanylpropyl)-1,3-dioxan-5-yl]oxy]prop-2-enoate 在 三乙基硼 、 三(三甲基硅基)硅烷 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以91%的产率得到methyl 2-[(2R,4aR,6S,9aS)-2-(4-methoxyphenyl)-7-oxo-4a,8,9,9a-tetrahydro-4H-[1,3]dioxino[5,4-b]oxepin-6-yl]acetate
  参考文献：
  名称：

  A Concise Route to Two Distinct E-Ring Structures of Ciguatoxins

  摘要：

  Ciguatoxins, the causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers, and known to have more than 20 structurally distinct congeners. In this paper, we describe a new concise synthesis of the two E-ring structures, of different ring sizes, found in ciguatoxins. From the common oxepane intermediate, the seven-membered E-ring was prepared in three steps, and the eight-membered E-ring was synthesized in seven steps using ring expansion and olefin isomerization as key reactions.

  DOI：

  10.3987/com-06-s(k)16