diethyl (3R,3aS,6aR)-hexahydro-2-[(S)-1-phenylethyl]-2H-cyclopenta[d]isoxazol-3-yl-3-phosphonate | 1093380-51-8

• 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: diethyl (3R,3aS,6aR)-hexahydro-2-[(S)-1-phenylethyl]-2H-cyclopenta[d]isoxazol-3-yl-3-phosphonate
• 英文别名: (3R,3aS,6aR)-3-[diethoxy(oxido)phosphaniumyl]-2-[(1S)-1-phenylethyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[d][1,2]oxazole
• CAS: 1093380-51-8
• 化学式: C₁₈H₂₈NO₄P
• 分子量: 353.398
• InChiKey: IRGPPAUMVKGPNT-DZJNRPSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (3R,3aS,6aR)-hexahydro-2-[(S)-1-phenylethyl]-2H-cyclopenta[d]isoxazol-3-yl-3-phosphonate 、 二碳酸二叔丁酯 在 Pd(OH)2/C 、 10% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 tert-butyl (3R,3aS,6aR)-hexahydro-3-diethoxyphosphorylcyclopenta[d]isoxazolidine-2-carboxylate 、 tert-butyl (2R,3R,3aS,6aR)-2-ethoxy-2-oxocyclopenta[d](1,2-oxaphospholan-3-yl)carbamate 、
  参考文献：
  名称：

  Stereochemistry of cycloaddition of (S)-N-(1-phenylethyl)-C-phosphorylated nitrone with cyclopentene and 2,3-dihydrofuran

  摘要：

  Cycloaddition of(S)-N-(1-phenylethyl)-C-(diethoxyphosphoryl)nitrone to cyclopentene gave a mixture of diethyl (3S,3aR,6aS)- and (3R,3aS,6aR)-hexahydro-2-[(S)-1-phenylethyl-2H-cyclopenta[d]isoxazol-3-yl-3-phosphonates with moderate (68:32) diastereoselectivity, while the reaction with 2,3-dihydrofuran led regiospecifically to the formation of an easily separable mixture of diethyl (3S,3aR,6aR)- and (3R,3aS,6aS)-hexahydro-2-[(S)-1-phenylethyl]furo[3,2-d]isoxazol-3-yl-3-phosphonates in a 65:35 ratio. Absolute configurations of cycloadducts Were established based on conformational analyses employing H-1 and C-13 NMR data and confirmed by 2D NOE experiments. Diastereoisomeric diethyl (3S,3aR,6aS)and (3R,3aS,6aR)-hexahydro-2-[(S)-1-phenylethyl-2H-cyclopenata[d]isoxazol-3-yl-3-phosphonates were transformed into both enantiomers of tert-butyl (2S,3S,3aR,6aS)- and (2R,3R,3aS,6aR)-2-ethoxy-2-oxo-cyclopenta[d](1,2-oxaphospholan-3-yl)carbamates in good yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.09.027
• 作为产物：
  描述：

  N-[(S)-1-phenylethyl]-C-(diethoxyphosphoryl)nitrone 、 环戊烯 以 甲苯 为溶剂， 以54%的产率得到diethyl (3S,3aR,6aS)-hexahydro-2-[(S)-1-phenylethyl]-2H-cyclopenta[d]isoxazol-3-yl-3-phosphonate
  参考文献：
  名称：

  Stereochemistry of cycloaddition of (S)-N-(1-phenylethyl)-C-phosphorylated nitrone with cyclopentene and 2,3-dihydrofuran

  摘要：

  Cycloaddition of(S)-N-(1-phenylethyl)-C-(diethoxyphosphoryl)nitrone to cyclopentene gave a mixture of diethyl (3S,3aR,6aS)- and (3R,3aS,6aR)-hexahydro-2-[(S)-1-phenylethyl-2H-cyclopenta[d]isoxazol-3-yl-3-phosphonates with moderate (68:32) diastereoselectivity, while the reaction with 2,3-dihydrofuran led regiospecifically to the formation of an easily separable mixture of diethyl (3S,3aR,6aR)- and (3R,3aS,6aS)-hexahydro-2-[(S)-1-phenylethyl]furo[3,2-d]isoxazol-3-yl-3-phosphonates in a 65:35 ratio. Absolute configurations of cycloadducts Were established based on conformational analyses employing H-1 and C-13 NMR data and confirmed by 2D NOE experiments. Diastereoisomeric diethyl (3S,3aR,6aS)and (3R,3aS,6aR)-hexahydro-2-[(S)-1-phenylethyl-2H-cyclopenata[d]isoxazol-3-yl-3-phosphonates were transformed into both enantiomers of tert-butyl (2S,3S,3aR,6aS)- and (2R,3R,3aS,6aR)-2-ethoxy-2-oxo-cyclopenta[d](1,2-oxaphospholan-3-yl)carbamates in good yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.09.027

文献信息

• Stereochemistry of cycloaddition of (S)-N-(1-phenylethyl)-C-phosphorylated nitrone with cyclopentene and 2,3-dihydrofuran
  作者：Dorota G. Piotrowska

  DOI：10.1016/j.tetasy.2008.09.027

  日期：2008.10

  Cycloaddition of(S)-N-(1-phenylethyl)-C-(diethoxyphosphoryl)nitrone to cyclopentene gave a mixture of diethyl (3S,3aR,6aS)- and (3R,3aS,6aR)-hexahydro-2-[(S)-1-phenylethyl-2H-cyclopenta[d]isoxazol-3-yl-3-phosphonates with moderate (68:32) diastereoselectivity, while the reaction with 2,3-dihydrofuran led regiospecifically to the formation of an easily separable mixture of diethyl (3S,3aR,6aR)- and (3R,3aS,6aS)-hexahydro-2-[(S)-1-phenylethyl]furo[3,2-d]isoxazol-3-yl-3-phosphonates in a 65:35 ratio. Absolute configurations of cycloadducts Were established based on conformational analyses employing H-1 and C-13 NMR data and confirmed by 2D NOE experiments. Diastereoisomeric diethyl (3S,3aR,6aS)and (3R,3aS,6aR)-hexahydro-2-[(S)-1-phenylethyl-2H-cyclopenata[d]isoxazol-3-yl-3-phosphonates were transformed into both enantiomers of tert-butyl (2S,3S,3aR,6aS)- and (2R,3R,3aS,6aR)-2-ethoxy-2-oxo-cyclopenta[d](1,2-oxaphospholan-3-yl)carbamates in good yields. (C) 2008 Elsevier Ltd. All rights reserved.