(S)-4-nitro-3-phenyl-1-(4-(trifluoromethyl)phenyl)butan-1-one | 1370417-62-1

• 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: (S)-4-nitro-3-phenyl-1-(4-(trifluoromethyl)phenyl)butan-1-one
• 英文别名: (3S)-4-nitro-3-phenyl-1-[4-(trifluoromethyl)phenyl]butan-1-one
• CAS: 1370417-62-1
• 化学式: C₁₇H₁₄F₃NO₃
• 分子量: 337.298
• InChiKey: GGGLIJIFFSKMLW-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4'-三氟甲基苯乙酮 、 β-硝基苯乙烯 在 1-[(1R,2R)-2-aminocyclohexyl]-3-[(1R,2R)-2-[(4-methylphenyl)sulfonylamino]-1,2-diphenylethyl]thiourea 、 苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以87%的产率得到(S)-4-nitro-3-phenyl-1-(4-(trifluoromethyl)phenyl)butan-1-one
  参考文献：
  名称：

  带有多个氢键供体的手性伯胺催化芳族酮和丙酮与硝基烯烃的对映选择性共轭加成反应

  摘要：

  设计并合成了带有多个氢键供体的新型手性伯胺催化剂。新开发的双功能有机催化剂不仅能以良好的收率（97→99％ee）以良好的收率（高达87％）高效催化芳族酮对硝基烯烃的对映选择性共轭加成，而且还能以优异的收率（90催化丙酮）将丙酮对硝基选择性共轭加成。 –96％）具有高对映选择性（高达97％ee）。

  DOI：

  10.1021/jo300011x

文献信息

• Exploitation of Dimeric Cyclic Cysteine as Helix Inducer in Ultra‐Short Peptides for Cu(II)‐Catalyzed Asymmetric Michael Addition on Chalcones
  作者：Giorgio Facchetti、Jaime Gracia Vitoria、Martina Moraschi、Raffaella Bucci、Anne Catherine Abel、Stefano Pieraccini、Sara Pellegrino、Isabella Rimoldi

  DOI：10.1002/ejoc.202300240

  日期：2023.5.12

  Cyclic cysteine analogues were efficiently used as constrained unnatural amino acids proving able to induce stable conformation in Leu-Val containing peptides. These ultra-short peptides were then used as chiral ligands in copper(II) complexes and applied to the asymmetric Michael addition on differently substituted chalcones.

  环状半胱氨酸类似物被有效地用作受限非天然氨基酸，证明能够在含有 Leu-Val 的肽中诱导稳定构象。然后将这些超短肽用作铜 (II) 配合物中的手性配体，并应用于不同取代的查耳酮的不对称迈克尔加成。
• Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines
  作者：Jesús Flores-Ferrándiz、Alexander Stiven、Lia Sotorríos、Enrique Gómez-Bengoa、Rafael Chinchilla

  DOI：10.1016/j.tetasy.2015.07.011

  日期：2015.9

  Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched beta-substituted gamma-nitroketones. The reaction was performed in the presence of 3,4-dimethoxybenzoic acid as an additive, in chloroform as the solvent at room temperature, achieving enantioselectivities up to 96%. Theoretical calculations are used to justify the observed sense of the stereoinduction. (C) 2015 Elsevier Ltd. All rights reserved.
• Enantioselective Conjugate Addition of Both Aromatic Ketones and Acetone to Nitroolefins Catalyzed by Chiral Primary Amines Bearing Multiple Hydrogen-Bonding Donors
  作者：Zhong-Wen Sun、Fang-Zhi Peng、Ze-Qian Li、Li-Wei Zou、Shao-Xiong Zhang、Xiang Li、Zhi-Hui Shao

  DOI：10.1021/jo300011x

  日期：2012.4.20

  of chiral primary amine catalysts bearing multiple hydrogen-bonding donors have been designed and synthesized. The newly developed bifunctional organocatalysts efficiently catalyzed not only enantioselective conjugate addition of aromatic ketones to nitroolefins in good yields (up to 87%) with excellent enantioselectivities (97→99% ee) but also enantioselective conjugate addition of acetone to nitroolefins

  设计并合成了带有多个氢键供体的新型手性伯胺催化剂。新开发的双功能有机催化剂不仅能以良好的收率（97→99％ee）以良好的收率（高达87％）高效催化芳族酮对硝基烯烃的对映选择性共轭加成，而且还能以优异的收率（90催化丙酮）将丙酮对硝基选择性共轭加成。 –96％）具有高对映选择性（高达97％ee）。