(S)-2-((R)-2-nitro-1-(4-dimethylaminophenyl)ethyl)cyclohexanone | 942149-09-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-((R)-2-nitro-1-(4-dimethylaminophenyl)ethyl)cyclohexanone
• 英文别名: (2S)-2-[(1R)-1-[4-(dimethylamino)phenyl]-2-nitroethyl]cyclohexan-1-one
• CAS: 942149-09-9
• 化学式: C₁₆H₂₂N₂O₃
• 分子量: 290.362
• InChiKey: AUIBPQKHFNUHNU-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-nitro-2-(4'-dimethylaminophenyl)ethene 、 环己酮 在 1-[(2S)-pyrrolidin-2-yl]-N-[[2,4,6-triethyl-3,5-bis[[[(2S)-pyrrolidin-2-yl]methylamino]methyl]phenyl]methyl]methanamine 作用下， 以 二氯甲烷 为溶剂， 反应 26.75h， 以88%的产率得到(S)-2-((R)-2-nitro-1-(4-dimethylaminophenyl)ethyl)cyclohexanone
  参考文献：
  名称：

  C3-对称脯氨酸功能化有机催化剂：对映选择性迈克尔加成反应

  摘要：

  基于 1,3,5-三乙苯的 C 3 -对称三足催化剂 4 结合了分子受体的特征，显示出以高立体选择性（高达 99: 1 dr 和高达 98 % ee)。

  DOI：

  10.1002/ejoc.201000569

文献信息

• An Ionic Liquid Containing L-Proline Moiety as Highly Efficient and Recyclable Chiral Organocatalyst for Michael Addition
  作者：Jiang Li、Xia Bing Li、Sha Sha Ma、Juan Liu、Ben Hao Li、Bao Lin Li

  DOI：10.1002/bkcs.10848

  日期：2016.8

  A novel chiral ionic liquid containing proline moiety was synthesized. It can be used as a highly efficient and recyclable chiral organocatalyst for Michael addition of cyclohexanone with (E)‐β‐nitroalkenes in methanol at room temperature. The Michael addition affords the corresponding products in satisfactory yields of isolated products (78–98%) with high diastereoselectivities and excellent enantioselectivities

  合成了一种新型的含有脯氨酸部分的手性离子液体。它可以用作高效和可回收的手性有机催化剂，用于在室温下在甲醇中将环己酮与（E）-β-硝基烯烃进行迈克尔加成反应。迈克尔加成物以高非对映选择性和出色的对映选择性（高达98％dr和高达99％ee）提供令人满意的分离产物（78-98％）的相应产物。催化剂可循环使用多达五次，而收率和立体选择性均不降低。
• Functionalized proline with double hydrogen bonding potential: highly enantioselective Michael addition of carbonyl compounds to β-nitrostyrenes in brine
  作者：Satyajit Saha、Saona Seth、Jarugu Narasimha Moorthy

  DOI：10.1016/j.tetlet.2010.07.164

  日期：2010.10

  synthetic manipulation of S-proline allows access to prolinamides 5–7 as organocatalysts capable of double hydrogen bonding for enantioselective Michael addition reactions of carbonyl compounds to β-nitrostyrenes. It is shown that prolinamide catalyst 7 leads to addition products with a high diastereo- as well as enantioselectivity. The transition state structure involving the binding of electrophilic

  简单地合成S-脯氨酸即可获得脯氨酰胺5 – 7作为能够双氢键合的有机催化剂，用于羰基化合物与β-硝基苯乙烯的对映选择性迈克尔加成反应。结果表明，脯氨酰胺催化剂7导致具有高非对映选择性和对映选择性的加成产物。据信涉及通过两个H键结合亲电硝基苯乙烯的过渡态结构通过由甲苯磺酰基环介导的π，π堆积相互作用而进一步稳定。
• Enantioselective Michael Addition of Cyclohexanone to Nitroolefins Catalyzed by a New Pyrrolidinyl-isosteviol Bifunctional Organocatalyst in Water
  作者：Yu-Xia Liu、Yuan-Yuan Xu、Shuai Li、Zi-Qing Pan、Bing-Xue Li、Zhao-Yang Fan

  DOI：10.2174/1570178620666230801141834

  日期：2024.2

  A new pyrrolidinyl-isosteviol bifunctional organocatalyst was synthesized, which was applied to catalyze the asymmetric Michael addition between cyclohexanone and nitroolefins. With 10 mol % of the organocatalyst, the reaction proceeded in water in high yields (up to 99%) with excellent diastereoselectivities (anti/syn up to 98:2) and good enantioselectivities (up to 90% ee). The design of the proline-isosteviol

  合成了一种新型吡咯烷基-异甜菊醇双功能有机催化剂，用于催化环己酮与硝基烯烃之间的不对称迈克尔加成反应。使用 10 mol% 的有机催化剂，反应在水中以高产率（高达 99%）进行，并具有优异的非对映选择性（反/顺高达 98:2）和良好的对映选择性（高达 90% ee）。脯氨酸-异甜菊醇缀合物作为有机催化剂的设计基于脯氨酸在烯胺形成中的关键作用。综上所述，合成了一种新型吡咯烷基-异甜菊醇双功能有机催化剂，能够有效催化多种硝基烯烃与环己酮的CC形成反应。
• Polystyrene supported benzoylthiourea—pyrrolidine organocatalyst for the enantioselective Michael addition
  作者：Ladislav Androvič、Pavel Drabina、Markéta Svobodová、Miloš Sedlák

  DOI：10.1016/j.tetasy.2016.06.015

  日期：2016.9

  Herein the preparation of a swellable pearl-like copolymer of styrene with anchored (S)-1-benzoyl-3-(pyrrolidine-2-ylmethyl)thiourea (20-600 mu m) and its application as a recyclable organocatalyst for the Michael addition of ketones to functionalized beta-nitrostyrenes is described. The rate of the reaction taking place in the matrix of the swellable polymeric catalyst was comparable with the reaction rate in homogeneous medium. The corresponding functionalized 4-nitroketones were formed quantitatively with the enantiomeric excesses up to 98% ee. After a fivefold recycling of the catalyst, no decrease in the yield was detected, but the enantioselectivity was slightly lowered (95 -> 88% ee). (C) 2016 Elsevier Ltd. All rights reserved.