(R)-5-nitro-4-(4-(trifluoromethyl)phenyl)pentan-2-one | 1627695-52-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-5-nitro-4-(4-(trifluoromethyl)phenyl)pentan-2-one
• 英文别名: (R)-4-[4-(Trifluoromethyl)phenyl]-5-nitropentane-2-one；(4R)-5-nitro-4-[4-(trifluoromethyl)phenyl]pentan-2-one
• CAS: 1627695-52-6
• 化学式: C₁₂H₁₂F₃NO₃
• 分子量: 275.227
• InChiKey: GSGPFCZJDQHLMP-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  1-(2-nitrovinyl)-4-trifluoromethylbenzene 、 丙酮 在 1-((1R,2R)-2-aminocyclohexyl)-3-(9H-fluoren-9-yl)thiourea 、 对甲基苯甲酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以67%的产率得到
  参考文献：
  名称：

  New simple primary amine–thiourea organocatalysts and their application in asymmetric conjugate addition

  摘要：

  DOI：

  10.1016/j.tetlet.2014.05.006

文献信息

• Concentration Effect in the Asymmetric Michael Addition of Acetone to β-Nitrostyrenes Catalyzed by Primary Amine Thioureas
  作者：Ciril Jimeno、Miquel Pericàs、Z. Günler、Ignacio Alfonso

  DOI：10.1055/s-0036-1589408

  日期：——

  yield and ee of the Michael­ addition products. Bifunctional primary amine thiourea (PAT) organocatalysts show remarkable improvement in enantioselectivity and catalytic activity (turnover frequency) in the asymmetric Michael addition of acetone to β-nitrostyrenes upon dilution. Mechanistic investigations indicate that this behavior corresponds to the inhibition of off-cycle catalyst deactivation at low

  献给教授迪特尔·恩德斯在他70之际个生日 抽象的 双功能伯胺硫脲（PAT）有机催化剂在稀释后将丙酮不对称迈克尔加成至β-硝基苯乙烯中时，对映选择性和催化活性（转化频率）均得到显着改善。机理研究表明，这种行为对应于在低浓度下抑制循环外催化剂失活，而不是在高浓度下发生聚集现象。低浓度反应（在β-硝基苯乙烯中≤0.2M）导致催化剂失活最小化，从而使迈克尔加成产物的收率和ee最优化。 双功能伯胺硫脲（PAT）有机催化剂在稀释后将丙酮不对称迈克尔加成至β-硝基苯乙烯中时，对映选择性和催化活性（转化频率）均得到显着改善。机理研究表明，这种行为对应于在低浓度下抑制循环外催化剂失活，而不是在高浓度下发生聚集现象。低浓度反应（在β-硝基苯乙烯中≤0.2M）导致催化剂失活最小化，从而使迈克尔加成产物的收率和ee最优化。
• Asymmetric Michael addition of ketones to nitroolefins: pyrrolidinyl-oxazole-carboxamides as new efficient organocatalysts
  作者：Ahmed Kamal、Manda Sathish、Vunnam Srinivasulu、Jadala Chetna、Kunta Chandra Shekar、Shalini Nekkanti、Yellaiah Tangella、Nagula Shankaraiah

  DOI：10.1039/c4ob01223b

  日期：——

  Chiral pyrrolidinyl-oxazole-carboxamides were synthesized and used as efficient new organocatalysts for the asymmetric Michael addition of ketones with nitroalkenes under solvent-free conditions. Gratifyingly, the corresponding Michael adducts were obtained in higher yields (up to 99%) and excellent stereoselectivities (up to >99/1 dr and 99% ee). Transition state models have been proposed to account

  合成了手性吡咯烷基-恶唑-羧酰胺，并将其用作高效的新型有机催化剂，用于在无溶剂条件下将酮与硝基烯烃不对称迈克尔加成。令人欣慰的是，获得了相应的迈克尔加合物，收率更高（高达99％）和出色的立体选择性（高达> 99/1 dr和99％ee）。已经提出过渡态模型来解释这些迈克尔加成反应的高对映选择性和非对映选择性，并且还已经使用密度泛函方法研究了能量学。这些结果支持优先形成的SYN通过的方式-产品反式-β-硝基苯经过重新的-面防烯胺。
• 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.