(1S,5S,6R)-6-((R)-3-Hydroxy-butoxy)-bicyclo[3.2.1]oct-2-en-8-one | 848873-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,5S,6R)-6-((R)-3-Hydroxy-butoxy)-bicyclo[3.2.1]oct-2-en-8-one
• CAS: 848873-89-2
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: NTCRQROIOYTENB-CHWFTXMASA-N

物化性质

• 沸点：
  371.0±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (1S,5S,6R)-6-((R)-3-Hydroxy-butoxy)-bicyclo[3.2.1]oct-2-en-8-one 在 palladium on activated charcoal 吡啶 、 氢气 、 对甲苯磺酸 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Stereocontrolled intramolecular meta-arene–alkene photocycloaddition reactions using chiral tethers: efficiency of the tether derived from 2,4-pentanediol

  摘要：

  Photochemical reactions of substrates consisting of phenyl and vinyl groups, which are tethered with a chiral diol, resulted in intramolecular meta-arene-alkene cycloaddition; the reaction efficiency as well as the stereoselectivity was studied. 1,3-Butanediol, 2-substituted 1,3-propanediols, 2-methyl-2,4-penetanediol, and 2,6-dimethyl-3,5-heptanediol were employed as tethers, and the results are compared with those obtained with 2,4-pentanediol (PD) tether, which are known to show high stereoselectivity and moderate efficiency. All the reactions with the lower analogues were less efficient than with PD, although one of the butanediol-tethered reactions afforded a single stereoisomer as PD did. The dimethylheptanediol tether showed similar efficiency but lower stereoselectivity than PD. The results suggest that the PD tether has an optimized structure having a proper flexibility. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.086
• 作为产物：
  描述：

  在 盐酸 作用下， 以 丙酮 为溶剂， 反应 168.0h， 以40%的产率得到(1S,5S,6R)-6-((R)-3-Hydroxy-butoxy)-bicyclo[3.2.1]oct-2-en-8-one
  参考文献：
  名称：

  Stereocontrolled intramolecular meta-arene–alkene photocycloaddition reactions using chiral tethers: efficiency of the tether derived from 2,4-pentanediol

  摘要：

  Photochemical reactions of substrates consisting of phenyl and vinyl groups, which are tethered with a chiral diol, resulted in intramolecular meta-arene-alkene cycloaddition; the reaction efficiency as well as the stereoselectivity was studied. 1,3-Butanediol, 2-substituted 1,3-propanediols, 2-methyl-2,4-penetanediol, and 2,6-dimethyl-3,5-heptanediol were employed as tethers, and the results are compared with those obtained with 2,4-pentanediol (PD) tether, which are known to show high stereoselectivity and moderate efficiency. All the reactions with the lower analogues were less efficient than with PD, although one of the butanediol-tethered reactions afforded a single stereoisomer as PD did. The dimethylheptanediol tether showed similar efficiency but lower stereoselectivity than PD. The results suggest that the PD tether has an optimized structure having a proper flexibility. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.086