diethyl 2-acetamido-2-isopropylvinylphosphonate | 1044255-77-7

• 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 2-acetamido-2-isopropylvinylphosphonate
• 英文别名: N-[(E)-1-[diethoxy(oxido)phosphaniumyl]-3-methylbut-1-en-2-yl]acetamide
• CAS: 1044255-77-7
• 化学式: C₁₁H₂₂NO₄P
• 分子量: 263.274
• InChiKey: MYWQHAIKDPJNCT-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  70.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-acetamido-2-isopropylvinylphosphonate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 氢气 、 (S)-(-)-[(5,6),(5',6')-双(乙烯二氧)联苯-2,2'-基]二苯基磷 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、9.0 MPa 条件下， 反应 24.0h， 生成 (+)-diethyl 2-acetamido-2-isopropylethylphosphonate 、 (+)-diethyl 2-acetamido-2-isopropylethylphosphonate
  参考文献：
  名称：

  Synthesis of chiral β-aminophosphonates via Rh-catalyzed asymmetric hydrogenation of β-amido-vinylphosphonates

  摘要：

  The Rh-catalyzed asymmetric hydrogenation of prochiral beta-N-acetylamino-vinylphosphoniites allows the preparation of chiral beta-N-acetylamino-phosphonates with excellent yields (up to 100%) and. high enantioselectivities (up to 92% ee). The reaction is strongly dependent on the chiral bidentate phosphorus ligand and the solvent employed. In several cases an inversion of the induced chirality was noted by using the corresponding E- or Z-isomeric substrates. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.019
• 作为产物：
  描述：

  diethyl 2-amino-2-isopropylvinylphosphonate 、 乙酸酐 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以59%的产率得到diethyl 2-acetamido-2-isopropylvinylphosphonate
  参考文献：
  名称：

  Synthesis of chiral β-aminophosphonates via Rh-catalyzed asymmetric hydrogenation of β-amido-vinylphosphonates

  摘要：

  The Rh-catalyzed asymmetric hydrogenation of prochiral beta-N-acetylamino-vinylphosphoniites allows the preparation of chiral beta-N-acetylamino-phosphonates with excellent yields (up to 100%) and. high enantioselectivities (up to 92% ee). The reaction is strongly dependent on the chiral bidentate phosphorus ligand and the solvent employed. In several cases an inversion of the induced chirality was noted by using the corresponding E- or Z-isomeric substrates. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.019

文献信息

• Synthesis of chiral β-aminophosphonates via Rh-catalyzed asymmetric hydrogenation of β-amido-vinylphosphonates
  作者：Renat Kadyrov、Jens Holz、Benjamin Schäffner、Odalys Zayas、Juan Almena、Armin Börner

  DOI：10.1016/j.tetasy.2008.04.019

  日期：2008.5

  The Rh-catalyzed asymmetric hydrogenation of prochiral beta-N-acetylamino-vinylphosphoniites allows the preparation of chiral beta-N-acetylamino-phosphonates with excellent yields (up to 100%) and. high enantioselectivities (up to 92% ee). The reaction is strongly dependent on the chiral bidentate phosphorus ligand and the solvent employed. In several cases an inversion of the induced chirality was noted by using the corresponding E- or Z-isomeric substrates. (C) 2008 Elsevier Ltd. All rights reserved.