(2R,4R,5R)-4-(3-butenone-1-yl)-5-hydroxy-2-methyl-1,3-dioxane | 223575-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2R,4R,5R)-4-(3-butenone-1-yl)-5-hydroxy-2-methyl-1,3-dioxane
• CAS: 223575-77-7
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: WIYYSJAEAYWKMV-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.25
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,4R,5R)-4-(3-butenone-1-yl)-5-hydroxy-2-methyl-1,3-dioxane 在 palladium on activated charcoal 盐酸 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2S,4R,5R,E)-5-hydroxy-4-((3-methyl-2-pentenoic acid ethyl ester)-5-yl)-2-methyl-1,3-dioxane
  参考文献：
  名称：

  Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center

  摘要：

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.

  DOI：

  10.1021/jo9822380
• 作为产物：
  描述：

  (2S,4S,5R)-5-羟基-2-甲基-1,3-二恶烷-4-甲醛 、 1-三苯基膦-2-丙酮 以 四氢呋喃 为溶剂， 以75%的产率得到(2R,4R,5R)-4-(3-butenone-1-yl)-5-hydroxy-2-methyl-1,3-dioxane
  参考文献：
  名称：

  Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center

  摘要：

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.

  DOI：

  10.1021/jo9822380