diethyl 5-benzoyl-2-methyl-4-phenylisoxazolidin-3-yl-3-phosphonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl 5-benzoyl-2-methyl-4-phenylisoxazolidin-3-yl-3-phosphonate
• 英文别名: [(3R,4S,5R)-3-[diethoxy(oxido)phosphaniumyl]-2-methyl-4-phenyl-1,2-oxazolidin-5-yl]-phenylmethanone
• 化学式: C₂₁H₂₆NO₅P
• 分子量: 403.415
• InChiKey: FMHINKYDHNIRLO-CEWLAPEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-methyl-C-(diethoxyphosphoryl)nitrone 、 反式-查耳酮 以 甲苯 为溶剂， 反应 48.0h， 以50%的产率得到diethyl 5-benzoyl-2-methyl-4-phenylisoxazolidin-3-yl-3-phosphonate
  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

• Design, synthesis and cytotoxicity of a new series of isoxazolidines derived from substituted chalcones
  作者：Dorota G. Piotrowska、Marcin Cieślak、Karolina Królewska、Andrzej E. Wróblewski

  DOI：10.1016/j.ejmech.2011.01.067

  日期：2011.4

  A new series of isomeric isoxazolidin-3-yl-3-phosphonates were synthesised from N-methyl-C-diethoxyphosphorylnitrone and substituted chalcones. The respective isoxazolidin-3-yl-3-phosphonic acids were obtained from phosphonates via dealkylation procedure using trimethylsilyl bromide. Selected phosphonates and their respective phosphonic acids were screened for their cytotoxic activity to HeLa and K562

  一系列新的同分异构的异恶唑烷-3-基-3-膦酸酯由来自合成Ñ甲基Ç -diethoxyphosphorylnitrone和取代的查耳酮。使用三甲基甲硅烷基溴，通过脱烷基方法从膦酸酯获得相应的异恶唑烷-3--3-基膦酸。筛选选定的膦酸酯及其各自的膦酸对HeLa和K562细胞的细胞毒性活性，IC 50为0.1–0.3 mM。
• 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.