syn-3-ethyl-5-(1-hydroxyethyl)-4,5-dihydroisoxazole | 138587-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: syn-3-ethyl-5-(1-hydroxyethyl)-4,5-dihydroisoxazole
• 英文别名: (1R)-1-[(5R)-3-ethyl-4,5-dihydro-1,2-oxazol-5-yl]ethanol
• CAS: 138587-72-1
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: YWYWKTSKEOXBNQ-IYSWYEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  syn-3-ethyl-5-(1-hydroxyethyl)-4,5-dihydroisoxazole 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.5h， 生成 (2R,3R,5S)-5-Amino-5-ethyl-oct-7-ene-2,3-diol
  参考文献：
  名称：

  通过手性异恶唑啉简洁合成 β-氨基酸

  摘要：

  β-氨基酸是重要的合成目标，因为它们存在于各种天然产物、药物制剂和蛋白质结构基序的模拟物中。虽然含有成对取代模式的 β-氨基酸在这些情况下具有巨大的应用潜力，但对此类化合物的立体选择性制备的合成挑战迄今为止限制了更完整的研究。我们在这里提出了一种使用手性异恶唑啉作为关键中间体的直接方法，以优异的选择性获得五种不同的 β-氨基酸结构类型。特别值得注意的是使用这种方法来制备高度取代的顺-β-脯氨酸类似物。

  DOI：

  10.1021/ja0431713
• 作为产物：
  描述：

  1-(3-乙基-4,5-二氢-1,2-恶唑-5-基)乙酮 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以55%的产率得到syn-3-ethyl-5-(1-hydroxyethyl)-4,5-dihydroisoxazole
  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

文献信息

• A Concise Approach to Structurally Diverse β-Amino Acids
  作者：Aaron R. Minter、Amelia A. Fuller、Anna K. Mapp

  DOI：10.1021/ja0298747

  日期：2003.6.1

  We have demonstrated that the high yields and selectivities of 1,3-dipolar cycloadditions can be translated into facile stereoselective syntheses of a diverse array of beta-amino acids, key components of bioactive natural products, beta-lactams, and peptidomimetics. Simply by selecting different combinations of three readily available starting materials (an oxime, a chiral allylic alcohol, and a nucleophile), we used the reaction sequence to prepare four different beta-amino acid structural types with a variety of substitution patterns in good overall yield. Of particular note is the use of this approach to prepare highly substituted beta-amino acids not readily accessible by previously reported methodologies. This will pave the way for future studies of the structure and function of this important class of molecules.