ethyl 3,5-bis(diethoxyphosphoryl)-2-methylisoxazolidine-5-carboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: ethyl 3,5-bis(diethoxyphosphoryl)-2-methylisoxazolidine-5-carboxylate
• 英文别名: ethyl (3R,5S)-3,5-bis[diethoxy(oxido)phosphaniumyl]-2-methyl-1,2-oxazolidine-5-carboxylate
• 化学式: C₁₅H₃₁NO₉P₂
• 分子量: 431.36
• InChiKey: QIPOLTMENCUUNS-HIFRSBDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N-methyl-C-(diethoxyphosphoryl)nitrone 、 ethyl 2-diethoxyphosphinoylacrylate 以 甲苯 为溶剂， 反应 24.0h， 生成 ethyl 3,5-bis(diethoxyphosphoryl)-2-methylisoxazolidine-5-carboxylate 、 ethyl 3,5-bis(diethoxyphosphoryl)-2-methylisoxazolidine-5-carboxylate
  参考文献：
  名称：

  Stereochemistry of substituted isoxazolidines derived from N-methyl C-diethoxyphosphorylated nitrone

  摘要：

  Cycloadditions of N-methyl-C-(diethoxyphosphoryl)nitrone 1a to cyclic alkenes proceeded regio- and diastereospecifically. Reactions of la with 1, 1-disubstituted alkenes led to the regiospecific formation of 5,5-disubstituted isoxazolidines 7/8 in nearly equimolar ratios, whereas additions to trans- 1,2-disubstituted alkenes gave four isomeric isoxazolidines with up to 80% regioselectivity and moderate (up to 60%) diastereoselectivity. Stereochemistry of the substituted isoxazolidines was established based on the conformational analysis using vicinal H-H, H-P and P-C couplings, and was, in some cases, supported by geminal H-C-P=O coupling and deshielding P=O and C=O effects. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.011

文献信息

• Stereochemistry of substituted isoxazolidines derived from N-methyl C-diethoxyphosphorylated nitrone
  作者：Dorota G. Piotrowska

  DOI：10.1016/j.tet.2006.10.011

  日期：2006.12

  Cycloadditions of N-methyl-C-(diethoxyphosphoryl)nitrone 1a to cyclic alkenes proceeded regio- and diastereospecifically. Reactions of la with 1, 1-disubstituted alkenes led to the regiospecific formation of 5,5-disubstituted isoxazolidines 7/8 in nearly equimolar ratios, whereas additions to trans- 1,2-disubstituted alkenes gave four isomeric isoxazolidines with up to 80% regioselectivity and moderate (up to 60%) diastereoselectivity. Stereochemistry of the substituted isoxazolidines was established based on the conformational analysis using vicinal H-H, H-P and P-C couplings, and was, in some cases, supported by geminal H-C-P=O coupling and deshielding P=O and C=O effects. (c) 2006 Elsevier Ltd. All rights reserved.