(-)-(1S,3R,4R,7S,8R,11S)-7,11-dimethyl-4-hydroxy-3-iodomethyl-8-methoxycarbonyl-2-oxatricyclo<6.4.0.0^3,7>dodecane | 145315-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (-)-(1S,3R,4R,7S,8R,11S)-7,11-dimethyl-4-hydroxy-3-iodomethyl-8-methoxycarbonyl-2-oxatricyclo<6.4.0.0^3,7>dodecane
• 英文别名: methyl (3R,3aR,4aS,6S,8aR,8bS)-3-hydroxy-3a-(iodomethyl)-6,8b-dimethyl-1,2,3,4a,5,6,7,8-octahydrocyclopenta[b][1]benzofuran-8a-carboxylate
• CAS: 145315-23-7
• 化学式: C₁₆H₂₅IO₄
• 分子量: 408.277
• InChiKey: KLECDDKYWMPHQI-KZQACRCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(1S,3R,4R,7S,8R,11S)-7,11-dimethyl-4-hydroxy-3-iodomethyl-8-methoxycarbonyl-2-oxatricyclo<6.4.0.0^3,7>dodecane 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以98%的产率得到(+)-(1S,3R,7S,8R,11S)-7,11-dimethyl-3-iodomethyl-8-methoxycarbonyl-4-oxo-2-oxatricyclo<6.4.0.0^3,7>dodecane
  参考文献：
  名称：

  Enantioselective synthesis of an ent-trichothecene

  摘要：

  A convergent route for the enantioselective synthesis of trichothecenes is described. A key step in the synthetic sequence is an Ireland-Claisen rearrangement that occurs with total facial selectivity and high diastereoselectivity. The relative stereochemistry about the vicinal quaternary centers of the major diastereomer is that of the trichothecene skeleton, but the absolute stereochemistry is opposite to that of the natural products.

  DOI：

  10.1016/s0040-4020(01)80841-3
• 作为产物：
  描述：

  methyl (1R,2S,4S)-1-<3-hydroxy-1-methyl-2-methylenecyclopentyl>-2-methoxy-4-methylcyclohexanecarboxylate 在 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以87%的产率得到(-)-(1S,3R,4R,7S,8R,11S)-7,11-dimethyl-4-hydroxy-3-iodomethyl-8-methoxycarbonyl-2-oxatricyclo<6.4.0.0^3,7>dodecane
  参考文献：
  名称：

  Enantioselective synthesis of an ent-trichothecene

  摘要：

  A convergent route for the enantioselective synthesis of trichothecenes is described. A key step in the synthetic sequence is an Ireland-Claisen rearrangement that occurs with total facial selectivity and high diastereoselectivity. The relative stereochemistry about the vicinal quaternary centers of the major diastereomer is that of the trichothecene skeleton, but the absolute stereochemistry is opposite to that of the natural products.

  DOI：

  10.1016/s0040-4020(01)80841-3