(2R,3R,7R)-7-heptyl-2-(1-hydroxy-2-methylpropan-2-yl)-1,6-dioxaspiro[4.4]nonan-3-ol | 1252660-48-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,7R)-7-heptyl-2-(1-hydroxy-2-methylpropan-2-yl)-1,6-dioxaspiro[4.4]nonan-3-ol
• CAS: 1252660-48-2
• 化学式: C₁₈H₃₄O₄
• 分子量: 314.466
• InChiKey: ZNYXGEIEBNJWHA-LTBNCBHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,7R)-7-heptyl-2-(1-hydroxy-2-methylpropan-2-yl)-1,6-dioxaspiro[4.4]nonan-3-ol 在 magnesium oxide 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以86%的产率得到(2R,3R,5R,7R)-7-heptyl-2-(1-hydroxy-2-methylpropan-2-yl)-1,6-dioxaspiro[4.4]nonan-3-ol
  参考文献：
  名称：

  Stereocontrol of 5,5-Spiroketals in the Synthesis of Cephalosporolide H Epimers

  摘要：

  A blueprint for controlling the stereochemistry of oxygenated 5,5-spiroketals using chelation effects is provided. Chelation specifically of zinc salts (other protic and Lewis acids were less effective) between the spiroketal oxygen and an appropriately positioned alcohol group overrides normal biases in the preparation of 5,5-spiroketals, as illustrated by the stereocontrolled synthesis of epimeric cephalosporolide H isomers. This study provides new and valuable information for prescribing the chirality of the stereogenic core of 5,5-spiroketals.

  DOI：

  10.1021/ol102201z

文献信息

• Stereocontrol of 5,5-Spiroketals in the Synthesis of Cephalosporolide H Epimers
  作者：Sami F. Tlais、Gregory B. Dudley

  DOI：10.1021/ol102201z

  日期：2010.10.15

  A blueprint for controlling the stereochemistry of oxygenated 5,5-spiroketals using chelation effects is provided. Chelation specifically of zinc salts (other protic and Lewis acids were less effective) between the spiroketal oxygen and an appropriately positioned alcohol group overrides normal biases in the preparation of 5,5-spiroketals, as illustrated by the stereocontrolled synthesis of epimeric cephalosporolide H isomers. This study provides new and valuable information for prescribing the chirality of the stereogenic core of 5,5-spiroketals.