(1'R,2R,5'S)-6,8-dibromo-7-methoxy-6',6'-dimethyl-5-(2-methylpropyl)spiro[3H-chromene-2,2'-bicyclo[3.1.1]heptane]-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (1'R,2R,5'S)-6,8-dibromo-7-methoxy-6',6'-dimethyl-5-(2-methylpropyl)spiro[3H-chromene-2,2'-bicyclo[3.1.1]heptane]-4-one
• 化学式: C₂₂H₂₈Br₂O₃
• 分子量: 500.271
• InChiKey: LDONDBGUZSMKAG-ZNVLZIIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-4,6-dimethoxy-2-(methanesulfonyloxy)phenyl)ethanone 在 吗啉 、 sodium carbonate 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 4.33h， 生成 (1'R,2R,5'S)-6,8-dibromo-7-methoxy-6',6'-dimethyl-5-(2-methylpropyl)spiro[3H-chromene-2,2'-bicyclo[3.1.1]heptane]-4-one
  参考文献：
  名称：

  Stereoselective Synthesis Of Dimethylrobustadials

  摘要：

  A stereoselective synthesis of the methyl ethers of robustadials A and B (24) is described. The crucial step is the amine-catalyzed cyclization of the enone 8b which leads to the products 9b and 10b with high diastereoselectivity. The choice of the amine catalyst has a strong influence on the selectivity (i.e. on the ratio of trans and cis products 9b:10b); the amine must have an optimum pK(b) value. The aromatic synthon and the terpene synthon of robustadials are joined via a Prins reaction of a substituted benzaldehyde (3b) with beta-pinene (4). The reaction is strongly dependent on electronic effects, and the choice of substituents on the aromatic ring is critical. The use of (1S)-(-)-beta-pinene ensures the synthesis of enantiomerically pure compounds.

  DOI：

  10.1021/jo00101a031