(R)-1-(4-fluorophenyl)-4-nitro-3-phenylbutane-1-one

• 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: (R)-1-(4-fluorophenyl)-4-nitro-3-phenylbutane-1-one
• 英文别名: (R)-1-(4-fluorophenyl)-4-nitro-3-phenylbutan-1-one；1-(4-fluorophenyl)-4-nitro-3-phenylbutan-1-one；(3R)-1-(4-fluorophenyl)-4-nitro-3-phenylbutan-1-one
• 化学式: C₁₆H₁₄FNO₃
• 分子量: 287.29
• InChiKey: VKFYUNNVODDQAU-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  硝基甲烷 、 4'-fluorochalcone 在 C₄₃H₆₄N₄O₄ 、 scandium tris(trifluoromethanesulfonate) 、 4-二甲氨基吡啶 作用下， 反应 48.5h， 以99%的产率得到(R)-1-(4-fluorophenyl)-4-nitro-3-phenylbutane-1-one
  参考文献：
  名称：

  N，N'-二氧化物-Scan（III）配合物催化硝基甲烷与烯酮的不对称共轭加成反应

  摘要：

  以“ Sc”形式存在：将查尔酮和“肉桂酮”衍生物不对称共轭加成到硝基甲烷中，是通过使用简单有效的scan（III）-N，N'-二氧化物络合物作为催化剂实现的（参见方案） ）。在2-5 mol％的催化剂负载下，形成的相应产物的收率（高达99％）和对映选择性（高达ee > 99％  ）都非常好。

  DOI：

  10.1002/chem.201000688

文献信息

• Scope and Mechanism of Enantioselective Michael Additions of 1,3-Dicarbonyl Compounds to Nitroalkenes Catalyzed by Nickel(II)−Diamine Complexes
  作者：David A. Evans、Shizue Mito、Daniel Seidel

  DOI：10.1021/ja0735913

  日期：2007.9.1

  Readily prepared Ni(II)-bis[(R,R)-N,N'-dibenzylcyclohexane-1,2-diamine]Br(2) was shown to catalyze the Michael addition of 1,3-dicarbonyl compounds to nitroalkenes at room temperature in good yields with high enantioselectivities. The two diamine ligands in this system each play a distinct role: one serves as a chiral ligand to provide stereoinduction in the addition step while the other functions

  容易制备的 Ni(II)-双[(R,R)-N,N'-二苄基环己烷-1,2-二胺]Br(2) 在室温下可催化 1,3-二羰基化合物与硝基烯烃的迈克尔加成反应温度高，产率高，对映选择性高。该系统中的两个二胺配体各自发挥不同的作用：一个作为手性配体在加成步骤中提供立体诱导，而另一个作为底物烯醇化的基础。还研究了催化剂内的配体改性，以促进脂肪族硝基烯烃、1,3-二酮和 β-酮酸的反应。Ni(II)-双[(R,R)-N,N'-di-p-bromo-benzylcyclohex-1,2-diamine]Br(2) 在这些情况下被发现是一种有效的催化剂。此外，单二胺络合物，Ni(II)-[(R,R)-N,N'-二苄基环己烷-1,2-二胺]Br(2)，在水存在下催化加成反应。所提出的立体化学诱导模型显示与 X 射线结构分析一致。
• Highly Enantioselective Michael Addition of Nitroalkanes to Chalcones Using Chiral Squaramides as Hydrogen Bonding Organocatalysts
  作者：Wen Yang、Da-Ming Du

  DOI：10.1021/ol102294g

  日期：2010.12.3

  squaramide-based organocatalysts were facilely synthesized and applied as hydrogen bonding organocatalysts in the enantioselective Michael addition of nitroalkanes to chalcones. These organocatalysts promoted the Michael addition with low catalyst loading under high temperature (80 °C), affording the desired R or S enantiomers of the products flexibly in high yields with excellent enantioselectivities (93−96%

  容易地合成了一系列基于方酰胺的有机催化剂，并将其用作氢键键合的有机催化剂，用于将硝基烷烃向查尔酮进行对映选择性迈克尔加成反应。这些有机催化剂促进迈克尔加成与高温下低的催化剂负载量（80℃），得到所期望的- [R或小号以高收率和优异的对映选择性（93-96％ee）的由有机催化剂的合适的选择灵活的产品的对映体。
• Asymmetric Michael Addition of Aromatic Ketones to Nitroolefins Catalyzed by Simple Chiral Bifunctional Primary Amine-Thioureas
  作者：Liangliang Wang、Xiaoying Xu、Jun Huang、Lin Peng、Qingchun Huang、Lixin Wang

  DOI：10.2174/157017810791514652

  日期：2010.7.1

  Simple chiral primary amine-thiourea catalysts derived from chiral 1,2-diphenylethylenediamine were found to catalyze direct Michael addition of aromatic ketones to nitroolefins with good enantioselectives (up to 86% ee) and excellent yields (up to 97%) for a broad range of substrates and successfully used in the preparation of (R)-Balcofen.

  简单的手性一级胺-硫脲催化剂来源于手性1,2-二苯乙烯二胺，已被发现能够以良好的手性选择性（最高可达86% ee）和优异的产率（最高可达97%）催化芳香酮与硝基烯烃的直接迈克尔加成，适用于广泛的底物，并成功用于(R)-Balcofen的制备。
• Organocatalyzed highly stereoselective Michael addition of ketones to alkylidene malonates and nitroolefins using chiral primary-secondary diamine catalysts based on bispidine
  作者：Jie Liu、Zhigang Yang、Xiaohua Liu、Zhen Wang、Yanling Liu、Sha Bai、Lili Lin、Xiaoming Feng

  DOI：10.1039/b910939k

  日期：——

  based on bispidine have been developed to catalyze the asymmetric Michael addition of ketones to alkylidene malonates and nitroalkenes. The corresponding products were obtained in high yields (up to 99%) with high diastereoselectivities (up to 99:1) and high enantioselectivities (up to 97% ee) under mild conditions using either environmentally benign water as the solvent or no solvent.

  已经开发了包含基于联吡啶的伯-仲二胺的有机催化剂以催化酮向亚烷基丙二酸酯和硝基烯烃的不对称迈克尔加成。在温和条件下使用环境友好的方法，可以以高收率（高达99％），高非对映选择性（高达99：1）和高对映选择性（高达97％ee）获得相应的产物。水 作为溶剂或不使用溶剂。
• 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.