<1'R-(1'α,2'α,5'α)>-6,8-dibromo-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one | 128260-47-9

• 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'α,5'α)>-6,8-dibromo-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one
• 英文别名: (1'R-(1'α,2'α,5'α))-6,8-dibromo-5,7-dimethoxy-6',6'-dimethylspiro(2H-1-benzopyran-2,2'-bicyclo[3.1.1]heptan)-4(3H)-one；(1'R,2R,5'S)-6,8-dibromo-5,7-dimethoxy-6',6'-dimethylspiro[3H-chromene-2,2'-bicyclo[3.1.1]heptane]-4-one
• CAS: 128260-47-9
• 化学式: C₁₉H₂₂Br₂O₄
• 分子量: 474.189
• InChiKey: JQTYXSOVSKYIJS-LFVASHNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <1'R-(1'α,2'α,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 吗啉 正丁基锂 作用下， 以 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 5.0h， 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
• 作为产物：
  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 吗啉 正丁基锂 作用下， 以 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 3.5h， 生成 <1'R-(1'α,2'α,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

文献信息

• Stereoselective Synthesis Of Dimethylrobustadials
  作者：Marek Majewski、Nicholas M. Irvine、Gary W. Bantle

  DOI：10.1021/jo00101a031

  日期：1994.11

  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.