<1'R-(1'α,2'β,5'α)>-6,8-dibromo-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one | 160707-50-6

• 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-(1'α,2'β,5'α)>-6,8-dibromo-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one
• CAS: 160707-50-6
• 化学式: C₁₉H₂₂Br₂O₄
• 分子量: 474.189
• InChiKey: JQTYXSOVSKYIJS-NWJBQHJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  <1'R-(1'α,2'β,5'α)>-6,8-dibromo-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.5h， 以61%的产率得到(Z)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone
  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
• 作为产物：
  描述：

  Methanesulfonic acid 2,4-dibromo-6-[2-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1-hydroxy-ethyl]-3,5-dimethoxy-phenyl ester 在 sodium carbonate 草酰氯 、 sodium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.08h， 生成 <1'R-(1'α,2'β,5'α)>-6,8-dibromo-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-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