(R)-2-((S)-1-(4-bromophenyl)-2-nitroethyl)cyclohexan-1-one

• 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: (R)-2-((S)-1-(4-bromophenyl)-2-nitroethyl)cyclohexan-1-one
• 英文别名: (R)-2-((S)-1-(4-bromophenyl)-2-nitroethyl)cyclohexanone；(2R)-2-[(1S)-1-(4-bromophenyl)-2-nitroethyl]cyclohexan-1-one
• 化学式: C₁₄H₁₆BrNO₃
• 分子量: 326.19
• InChiKey: KBRMVECWZUGMGS-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环己酮 、 4-bromo-β-nitrostyrene 在 GAEIPKEMLRAQTNVILLNVLKQGDNYVYGIIKQVKEASNGEMELNEATLYTIFDR-((2R)-2-amino-3-[(3R)-pyrrolidin-3-yldisulfanyl]propanoyl)-EQDGIISSYWGDESQGGRRKYYRLTEIGHEAMRLAFESWSRVDKIIENLEANKKSEAIKSRGGSGGWSHPQFEK 作用下， 以86 %的产率得到(R)-2-((S)-1-(4-bromophenyl)-2-nitroethyl)cyclohexan-1-one
  参考文献：
  名称：

  烯胺催化环酮不对称迈克尔加成硝基烯烃的酶的设计和进化

  摘要：

  带有催化吡咯烷残基的设计人工酶通过烯胺催化促进了环酮与硝基烯烃的高度立体选择性迈克尔加成。在一项研究中，通过这种有效的酮功能化生物催化策略制备了多种手性 γ-硝基酮，该研究强调了人工酶在新自然反应中的效用。

  DOI：

  10.1002/anie.202404312

文献信息

• Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency
  作者：Jia-Rong Chen、Yi-Ju Cao、You-Quan Zou、Fen Tan、Liang Fu、Xiao-Yu Zhu、Wen-Jing Xiao

  DOI：10.1039/b925962g

  日期：——

  A series of thiourea-amine bifunctional catalysts have been developed by a rational combination of prolines with cinchona alkaloids, which are connected by a thiourea motif. The catalyst 3a, prepared from L-proline and cinchonidine, was found to be a highly efficient catalyst for the conjugate addition of ketones/aldehydes to a wide range of nitroalkenes (up to 98/2 dr and 96% ee). The privileged cinchonidine

  一系列 硫脲-胺双功能催化剂是通过脯氨酸与金鸡纳生物碱的合理组合而开发的，金鸡纳生物碱通过硫脲基序连接。催化剂3a由大号脯氨酸 和 辛可尼定被发现是一种高效的催化剂，用于将酮/醛共轭加成到各种各样的硝基烯烃中（高达98/2 dr和96％ee）。特权的辛可尼定骨架和硫脲基序对于反应活性和对映选择性是必不可少的。
• l-Proline derived triamine as a highly stereoselective organocatalyst for asymmetric Michael addition of cyclohexanone to nitroolefins
  作者：Haibin Chen、Yu Wang、Siyu Wei、Jian Sun

  DOI：10.1016/j.tetasy.2007.05.035

  日期：2007.6

  triamine 4 has been developed as a highly efficient and stereoselective organocatalyst for the asymmetric Michael addition of cyclohexanone to nitroolefins. In the presence of (CF3SO2)2NH, 4 catalyzed the reaction of cyclohexanone to a variety of nitroolefins with high yields (up to 99%) and excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to 98% ee).

  脯氨酸衍生的三胺4已被开发为一种高效且立体选择性的有机催化剂，用于环己酮向硝基烯烃的不对称迈克尔加成反应。在（CF 3 SO 2）2 NH存在下，4催化环己酮与各种硝基烯烃的反应，产率高（高达99％），非对映选择性（高达99：1 dr）和对映选择性（高达98）。 ％ee）。
• Novel bifunctional chiral squaramide-amine catalysts for highly enantioselective addition of mono and diketones to nitroalkenes
  作者：Ze Dong、Xiaoqing Jin、Pengcheng Wang、Chang Min、Jin Zhang、Zhe Chen、Hai-Bing Zhou、Chune Dong

  DOI：10.3998/ark.5550190.0012.927

  日期：——

  Novel bifunctional chiral squaramide–amine organocatalysts have been developed by rational combination of pyrrolidine and a cinchona alkaloid. The catalysts promoted the enantioselective Michael addition of both mono- and diketones to a broad range of nitroalkenes providing the corresponding products in moderate to high yields with excellent enantioselectivities and diastereoselectivities (up to 96%

  通过吡咯烷和金鸡纳生物碱的合理组合开发了新型双功能手性方酸酰胺-胺有机催化剂。该催化剂促进了单酮和二酮对广泛范围的硝基烯烃的对映选择性迈克尔加成，以中等至高产率提供相应的产物，具有优异的对映选择性和非对映选择性（产率高达 96%，96% ee，98:2 dr）。条件温和。这些结果表明，将两个手性特权骨架、吡咯烷和辛可宁与方酸酰胺连接器组装在一起是实现更广泛底物范围、高反应效率和对映选择性的有用策略。嵌入催化剂的两个主链之间手性的匹配对于提高对映选择性也很关键。
• Syntheses of Chiral Ferrocenophanes and Their Application to Asymmetric Catalysis
  作者：Qiying Zhang、Xiuling Cui、Lianmei Chen、Haitao Liu、Yangjie Wu

  DOI：10.1002/ejoc.201402985

  日期：2014.12

  easily synthesized from 1,1′-ferrocenedicarbaldehyde and aliphatic amines in high yields. One of the ferrocenophanes served as a ligand for the copper-catalyzed oxidative coupling of 2-naphthol derivatives to give the products in good yields with up to 92 % ee, and it also efficiently catalyzed the asymmetric Michael addition reaction as an organocatalyst.

  N-取代的 2-氮杂-[3]-二茂铁很容易从 1,1'-二茂铁二甲醛和脂肪胺以高产率合成。其中一种二茂铁作为配体用于铜催化的 2-萘酚衍生物氧化偶联，以高达 92% ee 的良好收率得到产物，并且它还作为有机催化剂有效催化不对称迈克尔加成反应。
• Resin-immobilized pyrrolidine-based chiral organocatalysts for asymmetric Michael additions of ketones and aldehydes to nitroolefins
  作者：Richeng Zhang、Guohui Yin、Yang Li、Xilong Yan、Ligong Chen

  DOI：10.1039/c4ra10684a

  日期：——

  Based on the electrostatic adsorption between acidic resins and organocatalysts, a series of resin-supported chiral organocatalysts were designed and synthesized. They were evaluated for the asymmetric Michael addition of cyclohexanone with nitrostyrene, in which, catalyst 3 (Fig. 1) exhibited the best catalytic performance. This reaction proceeded under catalyst 3 smoothly at room temperature without

  基于酸性树脂与有机催化剂之间的静电吸附作用，设计合成了一系列树脂负载的手性有机催化剂。对环己酮与硝基苯乙烯的不对称迈克尔加成反应进行了评估，其中催化剂3（图。1）表现出最佳的催化性能。该反应在催化剂3下在室温下平稳地进行，没有任何溶剂或添加剂，并且可以得到具有高产率（95％）和良好的立体选择性（90％ee，98∶2dr）的产物。令人鼓舞的是，催化剂3易于分离并连续使用16次，而反应对映选择性没有明显下降。此外，它已成功地用于催化一系列酮和醛与硝基烯烃的反应。