N-[(1S,2R)-2-hydroxy-1,4-diphenylbutyl]-P,P-diphenyl-N-[(1S)-1-phenylethyl]phosphinic amide

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: N-[(1S,2R)-2-hydroxy-1,4-diphenylbutyl]-P,P-diphenyl-N-[(1S)-1-phenylethyl]phosphinic amide
• 英文别名: (1S,2R)-1-[diphenylphosphoryl-[(1S)-1-phenylethyl]amino]-1,4-diphenylbutan-2-ol
• 化学式: C₃₆H₃₆NO₂P
• 分子量: 545.661
• InChiKey: BNQFEUAHTWGFPN-MCRCAKTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯丙醛 、 N-benzyl-P,P-diphenyl-N-[(1S)-1-phenylethyl]phosphinic amide 在 叔丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.5h， 以81%的产率得到N-[(1S,2R)-2-hydroxy-1,4-diphenylbutyl]-P,P-diphenyl-N-[(1S)-1-phenylethyl]phosphinic amide
  参考文献：
  名称：

  Phosphinamide-Directed Benzylic Lithiation. Application to the Synthesis of Peptide Building Blocks

  摘要：

  N-Benzyldiphenylphosphinamides are deprotonated at the NC alpha position diastereospecifically upon treatment with t-BuLi in diethyl ether at low temperature. The reaction of the anions with alkyl, acyl, and tin halides, aliphatic and aromatic aldehydes, and Michael acceptors allowed installation of a variety of functional groups into the benzylic arm in excellent yields. Cleavage of the P-N linkage affords 1,2-amino alcohols and alpha-, beta-, and gamma-amino acids.

  DOI：

  10.1021/ol7028096

文献信息

• Phosphinamide-Directed Benzylic Lithiation. Application to the Synthesis of Peptide Building Blocks
  作者：Pascual Oña Burgos、Ignacio Fernández、María José Iglesias、Santiago García-Granda、Fernando López Ortiz

  DOI：10.1021/ol7028096

  日期：2008.2.1

  N-Benzyldiphenylphosphinamides are deprotonated at the NC alpha position diastereospecifically upon treatment with t-BuLi in diethyl ether at low temperature. The reaction of the anions with alkyl, acyl, and tin halides, aliphatic and aromatic aldehydes, and Michael acceptors allowed installation of a variety of functional groups into the benzylic arm in excellent yields. Cleavage of the P-N linkage affords 1,2-amino alcohols and alpha-, beta-, and gamma-amino acids.