(4,5)-anti-(5,6)-syn-5,6-dihydroxy-2,2-dimethyl-4-methylheptan-3-one | 138587-95-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4,5)-anti-(5,6)-syn-5,6-dihydroxy-2,2-dimethyl-4-methylheptan-3-one
• CAS: 138587-95-8
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: CECMZQNNQAKXDA-CSMHCCOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (4,5)-anti-(5,5')-syn-3-tert-butyl-5-(1-hydroxyethyl)-4-methyl-4,5-dihydroisoxazole 在 氢气 、 硼酸 、 镍 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以54%的产率得到(4,5)-anti-(5,6)-syn-5,6-dihydroxy-2,2-dimethyl-4-methylheptan-3-one
  参考文献：
  名称：

  Nucleophilic additions to and reductiosn of 5-formyl-and 5-acyl-2-isoxazolines (4,5-dihydeoisoxazoles): a stereoselective route to β,γ-dihydroxy ketones

  摘要：

  Reductions of readily available 5-acyl-2-isoxazolines with L-Selectride follow the Felkin-Anh model and produce syn-5-hydroxyalkyl-2-isoxazolines with excellent (> 95:5) selectivities. Swern oxidation of 5-hydroxymethyl-2-isoxazolines, followed by direct addition of a Grignard reagent to the intermediate 5-formyl-2-isoxazolines, also follows the Felkin-Anh model and produces anti-5-hydroxyalkyl-2-isoxazolines with modest (80:20) to excellent (> 95:5) selectivity. In contrast, additions of Grignard reagents to 5-acyl-2-isoxazolines follow the chelation model, and give syn or anti products (depending on choice of acyl substituent and Grignard reagent) with good (90:10) to excellent selectivity. These selectivities are almost always far superior to those that can be obtained by direct nitrile oxide cycloaddition to a chiral allylic alcohol or ether. The resulting products are readily reduced to syn- or anti-beta,gamma-dihydroxy ketones. A speculative model to explain this surprising reversal in selectivity between formyl and acyl isoxazolines is proposed.

  DOI：

  10.1039/p19910002613