(+)-3-(3-nitrophenyl)-3-methoxyamino-1-phenyl-1-propanone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (+)-3-(3-nitrophenyl)-3-methoxyamino-1-phenyl-1-propanone
• 英文别名: 3-(Methoxyamino)-3-(3-nitrophenyl)-1-phenylpropan-1-one
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: HITUXUPYGNHVKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-3-(3-nitrophenyl)-3-methoxyamino-1-phenyl-1-propanone 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以36%的产率得到(Z)-3-Amino-3-(3-nitro-phenyl)-1-phenyl-propenone
  参考文献：
  名称：

  A novel two-step preparation of enaminoketones by amination of α,β-unsaturated ketones with methoxyamine

  摘要：

  beta-Methoxyaminoketones, derived from the addition of methoxyamine to 1,3-diaryl-2-propen-1-one, underwent base-induced beta-elimination to furnish the corresponding enaminoketones in good to moderate yields. The reaction conditions and substituents on the substrates significantly influenced the selectivity in the production of enaminoketone and/or aziridineketone. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01801-2
• 作为产物：
  描述：

  3-氯苯甲酰乙腈 、 (E)-3-nitrochalcone 以 乙醇 为溶剂， 反应 4.0h， 以99%的产率得到(+)-3-(3-nitrophenyl)-3-methoxyamino-1-phenyl-1-propanone
  参考文献：
  名称：

  A novel two-step preparation of enaminoketones by amination of α,β-unsaturated ketones with methoxyamine

  摘要：

  beta-Methoxyaminoketones, derived from the addition of methoxyamine to 1,3-diaryl-2-propen-1-one, underwent base-induced beta-elimination to furnish the corresponding enaminoketones in good to moderate yields. The reaction conditions and substituents on the substrates significantly influenced the selectivity in the production of enaminoketone and/or aziridineketone. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01801-2

文献信息

• Lewis Acid−Lewis Acid Heterobimetallic Cooperative Catalysis:  Mechanistic Studies and Application in Enantioselective Aza-Michael Reaction
  作者：Noriyuki Yamagiwa、Hongbo Qin、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1021/ja054066b

  日期：2005.9.28

  3-3 mol % with enones. To broaden the substrate scope of the reaction to carboxylic acid derivatives, alpha,beta-unsaturated N-acylpyrroles were used as monodentate, carboxylic acid derivatives. With beta-alkyl-substituted N-acylpyrroles, the reaction proceeded smoothly and the products were obtained in high yield and good ee. Transformation of the 1,4-adducts from enones and alpha,beta-unsaturated N-acylpyrroles

  描述了由稀土-碱金属异双金属配合物促进的甲氧基胺催化不对称氮杂-迈克尔反应的全部细节，证明了路易斯酸-路易斯酸协同催化的有效性。首先，使用烯酮作为底物，以良好的产率 (57-98%) 和高 ee (81-96%) 获得 1,4-加合物。使用烯酮成功地将催化剂负载降低到 0.3-3 mol%。为了将反应的底物范围扩大到羧酸衍生物，α，β-不饱和 N-酰基吡咯被用作单齿羧酸衍生物。使用β-烷基取代的N-酰基吡咯，反应顺利进行，产物收率高，ee值好。来自烯酮和α的1,4-加合物的转化，β-不饱和N-酰基吡咯得到相应的手性氮丙啶和β-氨基酸。还描述了详细的机械研究，包括动力学、核磁共振分析、非线性效应和稀土金属效应。详细讨论了路易斯酸-路易斯酸协同机制，包括底物配位模式。
• A novel two-step preparation of enaminoketones by amination of α,β-unsaturated ketones with methoxyamine
  作者：Shinzo Seko、Nobuhiro Tani

  DOI：10.1016/s0040-4039(98)01801-2

  日期：1998.10

  beta-Methoxyaminoketones, derived from the addition of methoxyamine to 1,3-diaryl-2-propen-1-one, underwent base-induced beta-elimination to furnish the corresponding enaminoketones in good to moderate yields. The reaction conditions and substituents on the substrates significantly influenced the selectivity in the production of enaminoketone and/or aziridineketone. (C) 1998 Elsevier Science Ltd. All rights reserved.