(E)-N-[(3aR,7aR)-1,3-dibenzyl-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-1-phenylmethanimine | 1070876-88-8

• 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-phenylmethanimine
• CAS: 1070876-88-8
• 化学式: C₂₇H₃₀N₃OP
• 分子量: 443.528
• InChiKey: BYORFQKTJOUZNH-BFLZGIKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  32
• 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-phenylmethanimine 、 硝基甲烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以72%的产率得到
  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 、 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65%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-phenylmethanimine
  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<i>N</i>-Phosphonyl Imine Chemistry: Asymmetric Addition of Ketone-Derived Enolates for the Synthesis of β-Amino Ketones
  作者：Guigen Li、Jianlin Han、Teng Ai

  DOI：10.1055/s-2008-1067189

  日期：2008.8

  New chiral N-phosphonyl imines have been synthesized in good yields under convenient reaction conditions. These chiral N-phosphonyl imines can serve as efficient electrophiles for asymmetric addition reactions with lithium ketone enolates. Good chemical yields and excellent diastereoselectivities were obtained for twelve examples. The N-1-naphthyl group of the chiral auxiliary was found to be superior

  在方便的反应条件下，以良好的收率合成了新的手性 N-膦酰基亚胺。这些手性 N-膦酰基亚胺可作为有效的亲电子试剂与锂酮烯醇化物进行不对称加成反应。十二个实施例获得了良好的化学收率和优异的非对映选择性。发现手性助剂的 N-1-萘基在控制该反应的非对映选择性方面优于其苄基对应物。通过在室温下用甲醇中的 HBr 水溶液处理可以容易地除去手性助剂，从而以高收率得到游离的对氨基酮。
• Chiral N-phosphonyl imine chemistry: asymmetric 1,2-additions of allylmagnesium bromides
  作者：Adiseshu Kattuboina、Parminder Kaur、Thao Nguyen、Guigen Li

  DOI：10.1016/j.tetlet.2008.04.038

  日期：2008.6

  Chiral N-phosphonyl homoallylic amines were synthesized by the reaction of allylmagnesium bromide with chiral N-phosphonyl imines. The C-2-symmetric chiral N-phosphonyl group was optimized for this reaction. Excellent yields and good diastereoselectivities were obtained for eight examples. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.