[(5S)-3-hydroxymethyl-2-isoxazolin-5-yl]carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: [(5S)-3-hydroxymethyl-2-isoxazolin-5-yl]carboxylic acid methyl ester
• 英文别名: methyl (5S)-3-(hydroxymethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate
• 化学式: C₆H₉NO₄
• 分子量: 159.142
• InChiKey: LBPCNNHNCQXJJR-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-[(3R,5R)-(3-t-butyldimethylsilyloxymethyl-N-triisopropylsilyloxy-2-isoxazolidin-5-yl)carbonyl]-2-oxazolidinone 在 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.08h， 生成 [(5R)-3-hydroxymethyl-2-isoxazolin-5-yl]carboxylic acid methyl ester 、 [(5S)-3-hydroxymethyl-2-isoxazolin-5-yl]carboxylic acid methyl ester
  参考文献：
  名称：

  Silyl Nitronate Cycloadditions Catalyzed by Cu(II)-Bisoxazoline

  摘要：

  Cu(OTf)(2) and chiral BOX ligand-catalyzed 1,3-dipolar cydoadditions Of triisopropylsilyl nitronates with alpha,beta-unsaturated carboximides produced chiral isoxazolines in high yields, high enantioselectivities, and complete diastereoselectivities. These chiral isoxazoline products were further converted into structurally diversified derivatives, which demonstrated the utility of the new method of constructing isoxazolines. The transition-state structure of cydoaddition was proposed in the light of the relative and absolute configurations of the products.

  DOI：

  10.1021/acs.joc.5b02035

文献信息

• Silyl Nitronate Cycloadditions Catalyzed by Cu(II)-Bisoxazoline
  作者：Li Dong、Caiwei Geng、Peng Jiao

  DOI：10.1021/acs.joc.5b02035

  日期：2015.11.6

  Cu(OTf)(2) and chiral BOX ligand-catalyzed 1,3-dipolar cydoadditions Of triisopropylsilyl nitronates with alpha,beta-unsaturated carboximides produced chiral isoxazolines in high yields, high enantioselectivities, and complete diastereoselectivities. These chiral isoxazoline products were further converted into structurally diversified derivatives, which demonstrated the utility of the new method of constructing isoxazolines. The transition-state structure of cydoaddition was proposed in the light of the relative and absolute configurations of the products.