(1R,5S,6R)-6-((1R,3R)-3-Hydroxy-1-methyl-butoxy)-bicyclo[3.2.1]octan-8-one | 724432-54-6

• 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-((1R,3R)-3-Hydroxy-1-methyl-butoxy)-bicyclo[3.2.1]octan-8-one
• CAS: 724432-54-6
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: CEJAEMZWNTWZNR-PZWNZHSQSA-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-((1R,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：

  在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 丙酮 为溶剂， 生成 (1R,5S,6R)-6-((1R,3R)-3-Hydroxy-1-methyl-butoxy)-bicyclo[3.2.1]octan-8-one
  参考文献：
  名称：

  Regio- and diastereo-chemically controlled photocycloaddition of an arene and an alkene linked by a chiral auxiliary

  摘要：

  Intramolecular meta-arene-alkene photocycloaddition of 1b, the substrate having a chiral auxiliary as a linking bridge between the arene and the alkene, resulted in high diastereofacial differentiation of the alkene at the addition step and sufficient regiocontrol of the subsequent ring closure step to give a single diastereomer 4.

  DOI：

  10.1016/0957-4166(94)80147-9