Benzoic acid (R)-1-((4S,5R)-3-formyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester | 735317-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (R)-1-((4S,5R)-3-formyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester
• 英文别名: [(1R)-1-[(4S,5R)-3-formyl-4-methyl-4,5-dihydro-1,2-oxazol-5-yl]ethyl] benzoate
• CAS: 735317-37-0
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: LXLKRJCJVAXDEQ-OPQQBVKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzoic acid (R)-1-((4S,5R)-3-formyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester 在 镍 samarium diiodide 、 氢气 、 硼酸 、 双(三甲基硅烷基)氨基钾 、 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 55.58h， 生成 Benzoic acid (R)-1-{(4R,5S,6S)-6-[(3S,5S,6S,7S)-7-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-3,5-dimethyl-4-oxo-octyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl ester
  参考文献：
  名称：

  Stereochemically Rich Pentaketides from Bis(isoxazolines):  A General Strategy for Efficient Polyketide Synthesis

  摘要：

  A strategy based on diastereoselective dipolar cycloaddition reaction of nitrile oxides and allylic alcoholates has been applied to the synthesis of bis(isoxazolines) that are precursors to polyketide fragments. These intermediates can be elaborated into protected polyols by chemoselective reductive opening of each isoxazoline sequentially or, alternatively, both simultaneously, potentially providing access to all stereoisomers of this carbon skeleton.

  DOI：

  10.1021/ol0490633
• 作为产物：
  描述：

  Benzoic acid (R)-1-((4S,5R)-3-hydroxymethyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.83h， 以88%的产率得到Benzoic acid (R)-1-((4S,5R)-3-formyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester
  参考文献：
  名称：

  Stereochemically Rich Pentaketides from Bis(isoxazolines):  A General Strategy for Efficient Polyketide Synthesis

  摘要：

  A strategy based on diastereoselective dipolar cycloaddition reaction of nitrile oxides and allylic alcoholates has been applied to the synthesis of bis(isoxazolines) that are precursors to polyketide fragments. These intermediates can be elaborated into protected polyols by chemoselective reductive opening of each isoxazoline sequentially or, alternatively, both simultaneously, potentially providing access to all stereoisomers of this carbon skeleton.

  DOI：

  10.1021/ol0490633