methyl (5RS)-5-<(1RS)-1-hydroxyethyl>-3-phenyl-2-isoxazoline-5-carboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (5RS)-5-<(1RS)-1-hydroxyethyl>-3-phenyl-2-isoxazoline-5-carboxylate
• 英文别名: anti-5-Carbomethoxy-5-(1'-hydroxyethyl)-4,5-dihydroisoxazole；methyl (5R)-5-[(1R)-1-hydroxyethyl]-3-phenyl-4H-1,2-oxazole-5-carboxylate
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: WTYBMMOGDXGRKE-NOZJJQNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  benzohydroximoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 methyl (5RS)-5-<(1RS)-1-hydroxyethyl>-3-phenyl-2-isoxazoline-5-carboxylate
  参考文献：
  名称：

  通过羟肟基氯的O-金属化生成腈氧化物。氮氧化物与α-取代的烯丙醇的螯合控制的顺-选择性环加成反应

  摘要：

  据报道，通过用有机金属化合物处理羟肟基氯，新一代的腈氧化物。它们在1-位手性中心的烯丙醇上的环加成是以顺选择性方式进行的，这是借助金属螯合来立体控制1,3-偶极环加成的第一个例子。

  DOI：

  10.1016/0040-4039(91)80171-2

文献信息

• Lewis Acid Coordinated Nitrile Oxide and Nitrile Imine 1,3-Dipoles.<i>syn</i>-Selective Cycloadditions to 2-(1-Hydroxyalkyl)acrylates
  作者：Shuji Kanemasa、Shigeru Kobayashi

  DOI：10.1246/bcsj.66.2685

  日期：1993.9

  chlorides with organometallics or carbohydrazonoyl chlorides with metal alkoxides or amides offers a new generation of Lewis acid-coordinated nitrile oxide and nitrile imine 1,3-dipoles, respectively. These 1,3-dipole/Lewis acid complexes undergo syn-selective cycloaddition reactions to 2-(1-hydroxyalkyl)acrylates through a chelated transition state, while free dipoles show anti-selectivities.

  用有机金属化合物处理碳羟肟酰氯或用金属醇盐或酰胺处理碳腙酰氯分别提供了新一代路易斯酸配位的腈氧化物和腈亚胺 1,3-偶极子。这些 1,3-偶极/路易斯酸配合物通过螯合过渡态发生顺向选择性环加成反应生成 2-(1-羟基烷基)丙烯酸酯，而游离偶极则表现出反选择性。
• 1,3-Dipolar Cycloadditions to Baylis-Hillman Adducts: Rationale for the Observed Diastereoselectivity
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Laura Raimondi

  DOI：10.1021/jo00120a009

  日期：1995.7

  Diazomethane and benzonitrile oxide cycloadditions were performed on Baylis-Hillman adducts derived from methyl acrylate and aldehydes (beta'-alkoxy-alpha,beta-unsaturated esters). The reactions proceed in good chemical yields, and their stereochemical outcome can be explained by the ''inside alkoxy effect'' theory. In the case of diazomethane cycloadditions, however, electrostatic factors play a reduced role in comparison to the corresponding nitrile oxide reactions, while steric effects are of major importance in governing the stereoselectivity. This different behavior of the two 1,3-dipoles finds a rationale in the analysis of the atomic charges as calculated at the RHF/3-21G level of theory for the transition structure of these reactions.