10-epi-heliannuol A | 1217760-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: 10-epi-heliannuol A
• CAS: 1217760-49-0
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: FWVBSUZWRAYTJB-YMTOWFKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-benzyloxy-10α-hydroxy-7αH,11-heliannane 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到10-epi-heliannuol A
  参考文献：
  名称：

  A stereoselective route towards heliannuol A

  摘要：

  Both epimers of Heliannuol A, first heliannane reported in the literature, isolated from Heliannthus annuus, have been prepared individually in a stereoselective route using a ring closing metathesis (RCM) as a key step to obtain the eight-membered ring. Very good overall yield was obtained in both cases. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.03.105

文献信息

• Efficient and enantioselective total syntheses of heliannuols A and K
  作者：Makoto Kanematsu、Kana Soga、Yuki Manabe、Sachie Morimoto、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tet.2011.05.034

  日期：2011.7

  transfer in the Lewis acid mediated Claisen rearrangement of the allyl aryl ether for the key construction of a tertiary stereogenic center at the benzylic position followed by, for heliannuol A, ring-closing metathesis, diastereoselective epoxidation, and regioselective cleavage of the epoxide; and for heliannuol K, ring-closing metathesis and conjugate reduction of the eight-membered enone.

  Helennuol A的第二代对映选择性合成和Helennuol K的第一对映选择性全合成（通过两条途径）都已经有效地完成。（Heliannuol A，九步，产率为25％； Heliannuol K，七步，产率为47％）。我们合成策略的重点包括在路易斯酸介导的烯丙基芳基醚的Claisen重排中进行底物控制的手性转移，以​​关键性地构建苄基位置的叔立体异构中心，然后，对于Heliannuol A，进行闭环复分解，非对映选择性环氧化和环氧化物的区域选择性裂解；对于Helennuol K，八元烯酮的闭环复分解和共轭还原。
• A stereoselective route towards heliannuol A
  作者：Francisco A. Macías、David Chinchilla、Jose M.G. Molinillo、Frank R. Fronczek、Kozo Shishido

  DOI：10.1016/j.tet.2008.03.105

  日期：2008.6

  Both epimers of Heliannuol A, first heliannane reported in the literature, isolated from Heliannthus annuus, have been prepared individually in a stereoselective route using a ring closing metathesis (RCM) as a key step to obtain the eight-membered ring. Very good overall yield was obtained in both cases. (C) 2008 Published by Elsevier Ltd.