(E)-N-[(3aR,7aR)-1,3-dibenzyl-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-1-(4-bromophenyl)methanimine | 1093366-49-4

• 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: (E)-N-[(3aR,7aR)-1,3-dibenzyl-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-1-(4-bromophenyl)methanimine
• CAS: 1093366-49-4
• 化学式: C₂₇H₂₉BrN₃OP
• 分子量: 522.425
• InChiKey: HIZKEWWIKPADAT-UZSXMFRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (E)-N-[(3aR,7aR)-1,3-dibenzyl-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-1-(4-bromophenyl)methanimine 、 溴乙酸甲酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 methyl (2S,3S)-1-[(3aR,7aR)-1,3-dibenzyl-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-3-(4-bromophenyl)aziridine-2-carboxylate
  参考文献：
  名称：

  Chiral N-phosphonyl imine chemistry: new reagents and their applications for asymmetric reactions

  摘要：

  Novel chiral N-phosphonyl imines 2 have been designed and synthesized using chiral N-phosphoramide 1. These N-phosphonyl imines have been successfully utilized for asymmetric aza-Darzens reaction and asymmetric aza-Henry reaction. The C(2)-symmetric chiral auxiliary tolerates oxidation, is not sensitive to racemization and can be recycled for large scale synthesis. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.028
• 作为产物：
  描述：

  (3aR,7aR)-1,3-dibenzyl-2-hydroxy-2-imino-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphole 、 对溴苯甲醛 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以67%的产率得到(E)-N-[(3aR,7aR)-1,3-dibenzyl-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-1-(4-bromophenyl)methanimine
  参考文献：
  名称：

  Chiral N-phosphonyl imine chemistry: new reagents and their applications for asymmetric reactions

  摘要：

  Novel chiral N-phosphonyl imines 2 have been designed and synthesized using chiral N-phosphoramide 1. These N-phosphonyl imines have been successfully utilized for asymmetric aza-Darzens reaction and asymmetric aza-Henry reaction. The C(2)-symmetric chiral auxiliary tolerates oxidation, is not sensitive to racemization and can be recycled for large scale synthesis. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.028

文献信息

• Chiral N-phosphonyl imine chemistry: new reagents and their applications for asymmetric reactions
  作者：Adiseshu Kattuboina、Guigen Li

  DOI：10.1016/j.tetlet.2008.01.028

  日期：2008.3

  Novel chiral N-phosphonyl imines 2 have been designed and synthesized using chiral N-phosphoramide 1. These N-phosphonyl imines have been successfully utilized for asymmetric aza-Darzens reaction and asymmetric aza-Henry reaction. The C(2)-symmetric chiral auxiliary tolerates oxidation, is not sensitive to racemization and can be recycled for large scale synthesis. (c) 2008 Elsevier Ltd. All rights reserved.