(1R,5S,6R)-6-((1S,3R)-3-Hydroxy-1-methyl-butoxy)-bicyclo[3.2.1]octan-8-one | 724432-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,5S,6R)-6-((1S,3R)-3-Hydroxy-1-methyl-butoxy)-bicyclo[3.2.1]octan-8-one
• CAS: 724432-56-8
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: CEJAEMZWNTWZNR-CSYMLDBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,5S,6R)-6-((1S,3R)-3-Hydroxy-1-methyl-butoxy)-bicyclo[3.2.1]octan-8-one 在 4-甲基苯磺酸吡啶 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (1'R,5'S,6'R)-spiro[1,3-dioxolane-2,8'-bicyclo[3.2.1]octane]-6'-ol
  参考文献：
  名称：

  Asymmetric meta-arene–alkene photocycloaddition controlled by a 2,4-pentanediol tether

  摘要：

  Photo-irradiation of a substrate having phenyl and vinyl groups resulted in a stereocontrolled meta-arene-alkene cycloaddition when the two groups were connected by a chiral 2,4-pentanediol tether. The regioselectivity during the ring closing step after the initial addition was dependent on the stereochemistry of the tether and the photolysis conditions. The substrate bearing a p-tolyl or 3,5-xylyl group instead of the phenyl also underwent strict stereocontrolled addition. In the case of the o- and m-tolyl substrates, the regioselectivity due to the unsymmetric substitution of the arene moiety was also fully controlled. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.03.017
• 作为产物：
  描述：

  (1S,5R,7R)-7-((1S,3R)-3-Hydroxy-1-methyl-butoxy)-bicyclo[3.2.1]oct-2-en-8-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (1R,5S,6R)-6-((1S,3R)-3-Hydroxy-1-methyl-butoxy)-bicyclo[3.2.1]octan-8-one
  参考文献：
  名称：

  Asymmetric meta-arene–alkene photocycloaddition controlled by a 2,4-pentanediol tether

  摘要：

  Photo-irradiation of a substrate having phenyl and vinyl groups resulted in a stereocontrolled meta-arene-alkene cycloaddition when the two groups were connected by a chiral 2,4-pentanediol tether. The regioselectivity during the ring closing step after the initial addition was dependent on the stereochemistry of the tether and the photolysis conditions. The substrate bearing a p-tolyl or 3,5-xylyl group instead of the phenyl also underwent strict stereocontrolled addition. In the case of the o- and m-tolyl substrates, the regioselectivity due to the unsymmetric substitution of the arene moiety was also fully controlled. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.03.017