diisopropyl [(4-methoxyphenyl)amino](2-nitrophenyl)methylphosphonate

• 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: diisopropyl [(4-methoxyphenyl)amino](2-nitrophenyl)methylphosphonate
• 英文别名: 4-methoxy-N-[(R)-(2-nitrophenyl)-[oxido-di(propan-2-yloxy)phosphaniumyl]methyl]aniline
• 化学式: C₂₀H₂₇N₂O₆P
• 分子量: 422.418
• InChiKey: XYVSLPYHVNLYIW-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-methoxy-N-((E)-(2-nitrophenyl)methylidene)aniline 、 亚磷酸二异丙酯 在 (S)-(+)-3,3′-双(3,5-双(三氟甲基)苯基)-1,1′-联萘-2,2′-二基磷酸氢酯 作用下， 以 xylene 为溶剂， 反应 24.0h， 生成 diisopropyl [(4-methoxyphenyl)amino](2-nitrophenyl)methylphosphonate 、 diisopropyl [(4-methoxyphenyl)amino](2-nitrophenyl)methylphosphonate
  参考文献：
  名称：

  Chiral Brønsted Acid Catalyzed Enantioselective Hydrophosphonylation of Imines:  Asymmetric Synthesis of α-Amino Phosphonates

  摘要：

  A cyclic phosphoric acid derivative, derived from (R)-BINOL, was used as a chiral Bronsted acid (10 mol %) in hydrophosphonylation of aldimines with diisopropyl phosphite at room temperature. alpha-Amino phosphonates were obtained with good to high enantioselectivities.

  DOI：

  10.1021/ol050695e

文献信息

• Chiral Brønsted acid-catalyzed hydrophosphonylation of imines—DFT study on the effect of substituents of phosphoric acid
  作者：Takahiko Akiyama、Hisashi Morita、Prabhakar Bachu、Keiji Mori、Masahiro Yamanaka、Takashi Hirata

  DOI：10.1016/j.tet.2009.03.023

  日期：2009.6

  enantioselective hydrophosphonylation reaction of diisopropyl phosphite with aldimine furnished α-amino phosphonates with high enantioselectivities by means of a chiral phosphoric acid. DFT calculation of the effect of 3,3′-substituents of the phosphoric acid revealed the reason for the high enantioselectivities.

  亚磷酸二异丙酯与醛亚胺的对映体选择性氢膦酰化反应通过手性磷酸提供了高对映体选择性的α-氨基膦酸酯。DFT计算磷酸的3,3'取代基的效果揭示了高对映选择性的原因。
• EP1623971
  申请人：——

  公开号：——

  公开（公告）日：——
• Chiral Brønsted Acid Catalyzed Enantioselective Hydrophosphonylation of Imines:  Asymmetric Synthesis of α-Amino Phosphonates
  作者：Takahiko Akiyama、Hisashi Morita、Junji Itoh、Kohei Fuchibe

  DOI：10.1021/ol050695e

  日期：2005.6.1

  A cyclic phosphoric acid derivative, derived from (R)-BINOL, was used as a chiral Bronsted acid (10 mol %) in hydrophosphonylation of aldimines with diisopropyl phosphite at room temperature. alpha-Amino phosphonates were obtained with good to high enantioselectivities.