(S)-(-)-1-amino-1-(p-fluorophenyl)methylphosphonic acid | 503540-12-3

• 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: (S)-(-)-1-amino-1-(p-fluorophenyl)methylphosphonic acid
• 英文别名: [(S)-amino-(4-fluorophenyl)methyl]phosphonic acid
• CAS: 503540-12-3
• 化学式: C₇H₉FNO₃P
• 分子量: 205.126
• InChiKey: VNELARWUCSOVHC-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯酐 、 (S)-(-)-1-amino-1-(p-fluorophenyl)methylphosphonic acid 生成 (S)-N-phthaloyl-1-amino-1-(p-fluorophenyl)methylphosphonic acid
  参考文献：
  名称：

  A new efficient procedure for asymmetric synthesis of α-aminophosphonic acids via addition of lithiated bis(diethylamino)phosphine borane complex to enantiopure sulfinimines

  摘要：

  The addition of lithiated bis(diethylamino)phosphine borane complex to enantiopure p-toluenesulfinimines is highly diastereoselective, affording the corresponding addition products with high efficiency (yields from 72 to 100%). The addition products were readily converted into alpha-amino-alpha-arylmethylphosphonic acids with high enantiomeric purities (from 72 to >98%). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00684-5
• 作为产物：
  描述：

  (S_S)-(+)-N-p-toluenesulfinyl-1-amino-1-(p-fluorophenyl)methyl-bis(diethylamino)phosphine borane 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.0h， 以93%的产率得到(S)-(-)-1-amino-1-(p-fluorophenyl)methylphosphonic acid
  参考文献：
  名称：

  A new efficient procedure for asymmetric synthesis of α-aminophosphonic acids via addition of lithiated bis(diethylamino)phosphine borane complex to enantiopure sulfinimines

  摘要：

  The addition of lithiated bis(diethylamino)phosphine borane complex to enantiopure p-toluenesulfinimines is highly diastereoselective, affording the corresponding addition products with high efficiency (yields from 72 to 100%). The addition products were readily converted into alpha-amino-alpha-arylmethylphosphonic acids with high enantiomeric purities (from 72 to >98%). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00684-5

文献信息

• A new efficient procedure for asymmetric synthesis of α-aminophosphonic acids via addition of lithiated bis(diethylamino)phosphine borane complex to enantiopure sulfinimines
  作者：Marian Mikołajczyk、Piotr Łyżwa、Józef Drabowicz

  DOI：10.1016/s0957-4166(02)00684-5

  日期：2002.11

  The addition of lithiated bis(diethylamino)phosphine borane complex to enantiopure p-toluenesulfinimines is highly diastereoselective, affording the corresponding addition products with high efficiency (yields from 72 to 100%). The addition products were readily converted into alpha-amino-alpha-arylmethylphosphonic acids with high enantiomeric purities (from 72 to >98%). (C) 2002 Elsevier Science Ltd. All rights reserved.