N-[(3aR,7aR)-2-oxo-1,3-di(pentan-3-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-1-phenylmethanimine | 1186139-43-4

• 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: N-[(3aR,7aR)-2-oxo-1,3-di(pentan-3-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-1-phenylmethanimine
• CAS: 1186139-43-4
• 化学式: C₂₃H₃₈N₃OP
• 分子量: 403.548
• InChiKey: WCNVAWTWMKDDPK-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二苯亚甲基甘氨酸乙酯 、 N-[(3aR,7aR)-2-oxo-1,3-di(pentan-3-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-1-phenylmethanimine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl (2S,3S)-2-((diphenylmethylene)amino)-3-(((3aR,7aR)-2-oxido-1,3-di(pentan-3-yl)octahydrobenzo[d][1,3,2]diazaphosphol-2-yl)amino)-3-phenylpropanoate
  参考文献：
  名称：

  Chiral N-phosphonyl imine chemistry: Asymmetric synthesis of α,β-diamino esters by reacting phosphonyl imines with glycine enolates

  摘要：

  Chiral phosphonyl imines attached with N-isopropyl protection group were found to react with lithium glycine enolates under convenient conditions to give alpha,beta-diamino esters. Thirteen examples have been examined in good to excellent chemical yields (85-97%) diastereoselectivity (up to 99% de). By treating with HBr at room temperature, the chiral auxiliary can be readily removed and recycled. The absolute structure has been unambiguously determined by converting a product to a known sample. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.03.001

文献信息

• Asymmetric Synthesis of α-Amino-1,3-dithianes via Chiral <i>N</i>-Phosphonyl Imine-Based Umpolung Reaction Without Using Chromatography and Recrystallization
  作者：Padmanabha V. Kattamuri、Teng Ai、Suresh Pindi、Yinwei Sun、Peng Gu、Min Shi、Guigen Li

  DOI：10.1021/jo200070d

  日期：2011.4.15

  A series of alpha-amino-1,3-dithianes have been synthesized via the asymmetric Umpolung reaction of 2-lithio-1,3-dithianes with chiral N-phosphonyl imines in good chemical yields (up to 82%) and good to excellent diastereoselectivities (>99:1). The manner by which chiral N-phosphonyl imines are slowly added into the solution of 2-lithio-1,3-dithiane was found to be crucial for achieving excellent diastereoselectivity. The current synthesis was proven to follow the GAP chemistry (group-assistant-purification chemistry) process, which avoids traditional purification techniques of chromatography or recrystallization, i.e., the pure chiral alpha-amino-1,3-dithianes attached with the chiral N-phosphonyl group were readily obtained by washing the solid crude products with hexane or a mixture of hexane ethyl acetate.
• Chiral N-phosphonyl imine chemistry: Asymmetric synthesis of α,β-diamino esters by reacting phosphonyl imines with glycine enolates
  作者：Teng Ai、Guigen Li

  DOI：10.1016/j.bmcl.2009.03.001

  日期：2009.7

  Chiral phosphonyl imines attached with N-isopropyl protection group were found to react with lithium glycine enolates under convenient conditions to give alpha,beta-diamino esters. Thirteen examples have been examined in good to excellent chemical yields (85-97%) diastereoselectivity (up to 99% de). By treating with HBr at room temperature, the chiral auxiliary can be readily removed and recycled. The absolute structure has been unambiguously determined by converting a product to a known sample. Published by Elsevier Ltd.