(3aR,7aR)-N-[(R)-diethoxyphosphoryl-(4-fluorophenyl)methyl]-2-oxo-1,3-di(propan-2-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-amine | 1255703-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aR,7aR)-N-[(R)-diethoxyphosphoryl-(4-fluorophenyl)methyl]-2-oxo-1,3-di(propan-2-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-amine
• CAS: 1255703-22-0
• 化学式: C₂₃H₄₀FN₃O₄P₂
• 分子量: 503.534
• InChiKey: RLDWHDSFENFFSV-DNVJHFABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  71.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-[(3aR,7aR)-2-oxido-1,3-di(propan-2-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-ium-2-yl]-1-(4-fluorophenyl)methanimine 、 亚磷酸二乙酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 以91%的产率得到(3aR,7aR)-N-[(R)-diethoxyphosphoryl-(4-fluorophenyl)methyl]-2-oxo-1,3-di(propan-2-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-amine
  参考文献：
  名称：

  Research Article: Asymmetric Hydrophosphylation of Chiral N-Phosphonyl Imines Provides an Efficient Approach to Chiral α-Amino Phosphonates

  摘要：

  Chiral N‐phosphonylimines were found to react with lithium phosphites to provide various substituted chiral α‐amino phosphonates in excellent yields (94–97%) and diastereoselectivities (93:7–99:1). The types of bases utilized for generating the nucleophile are crucial for the effectiveness of asymmetric induction. In addition, N,N‐isopropyl group on chiral N‐phosphonylimine auxilliary was proven to be superior to other protecting groups in controlling diastereoselectivity. The absolute configuration was unambiguously determined by converting a chiral α‐amino phosphonate into its authentic N‐Cbz derivative.

  DOI：

  10.1111/j.1747-0285.2010.01013.x

文献信息

• Research Article: Asymmetric Hydrophosphylation of Chiral N-Phosphonyl Imines Provides an Efficient Approach to Chiral α-Amino Phosphonates
  作者：Parminder Kaur、Walter Wever、Trideep Rajale、Guigen Li

  DOI：10.1111/j.1747-0285.2010.01013.x

  日期：2010.10

  Chiral N‐phosphonylimines were found to react with lithium phosphites to provide various substituted chiral α‐amino phosphonates in excellent yields (94–97%) and diastereoselectivities (93:7–99:1). The types of bases utilized for generating the nucleophile are crucial for the effectiveness of asymmetric induction. In addition, N,N‐isopropyl group on chiral N‐phosphonylimine auxilliary was proven to be superior to other protecting groups in controlling diastereoselectivity. The absolute configuration was unambiguously determined by converting a chiral α‐amino phosphonate into its authentic N‐Cbz derivative.