(2R,3S)-2-ethyl-4-nitro-3-(4-(trifluoromethyl)phenyl)butanal | 1241905-70-3

• 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: (2R,3S)-2-ethyl-4-nitro-3-(4-(trifluoromethyl)phenyl)butanal
• 英文别名: (2R,3S)-2-ethyl-4-nitro-3-[4-(trifluoromethyl)phenyl]butanal
• CAS: 1241905-70-3
• 化学式: C₁₃H₁₄F₃NO₃
• 分子量: 289.254
• InChiKey: NZPJQTRCVAZYKS-CABZTGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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 、 正丁醛 在 水 、 L-proline lithium salt 作用下， 以 甲基叔丁基醚 为溶剂， 反应 30.0h， 以86%的产率得到(2R,3S)-2-ethyl-4-nitro-3-(4-(trifluoromethyl)phenyl)butanal
  参考文献：
  名称：

  脯氨酸锂盐催化的不对称迈克尔反应：L-脯氨酸和异吲哚异喹啉酮衍生物的高效合成

  摘要：

  锂使之成为可能：醛的对映选择性迈克尔加成到硝基烯烃是由容易获得的脯氨酸锂盐催化的。值得注意的是，不对称迈克尔反应在dr为23：1和ee为90％的情况下放大至50 mmol 。

  DOI：

  10.1002/chem.201202409

文献信息

• Epiandrosterone-derived prolinamide as an efficient asymmetric catalyst for Michael addition reactions of aldehydes to nitroalkenes
  作者：Yongchao Wang、Shen Ji、Kun Wei、Jun Lin

  DOI：10.1039/c4ra03075c

  日期：——

  Epiandrosterone derivatives-organocatalyzed asymmetric Michael addition of aldehydes to nitroalkenes was investigated. Among the various catalysts, a novel type of epiandrosterone-derived L-prolineamide catalyst was synthesized and exhibited better performance in both catalytic activity and stereoselectivity, providing the products with high yields (up to 98%), excellent enantioselectivities (up to

  研究了表雄甾酮衍生物-有机催化的醛向硝基烯烃的不对称迈克尔加成反应。在各种催化剂中，合成了新型的表雄甾酮衍生的L-脯氨酸酰胺催化剂，并在催化活性和立体选择性方面均表现出更好的性能，从而提供了高收率（高达98％），优异的对映选择性（高达99％ee）的产物。 ）和非对映选择性（高达99：1 dr），催化剂负载量低（5 mol％）。
• Prolylprolinol-Catalyzed Asymmetric Michael Addition of Aliphatic Aldehydes to Nitroalkenes
  作者：Dengfu Lu、Yuefa Gong、Weizhou Wang

  DOI：10.1002/adsc.200900687

  日期：2010.3.8

  Several novel prolylprolinol catalysts have been designed and synthesized. This type of compound showed high catalytic efficiency on promoting the direct addition of unmodified aldehydes to nitroalkenes. Among the catalysts surveyed, the least bulky member (8d) exhibited the best performance on both efficiency and stereoselectivity, providing the products with up to 97% ee value with 1.5–5 mol% catalyst

  已经设计和合成了几种新型的脯氨酰脯氨醇催化剂。这种类型的化合物在促进未改性的醛直接添加到硝基烯烃方面显示出高催化效率。在所调查的催化剂中，最小体积的成员（8d）在效率和立体选择性方面均表现出最佳性能，在1.5-5 mol％的催化剂负载量下，提供的产品具有高达97％ee的ee值。此外，已经进行了过渡态的计算研究，以解释高非对映选择性和对映选择性。
• Organocatalytic asymmetric Michael addition of aldehydes and ketones to nitroalkenes catalyzed by adamantoyl <scp>l</scp>-prolinamide
  作者：Yongchao Wang、Dong Li、Jun Lin、Kun Wei

  DOI：10.1039/c4ra11214h

  日期：——

  series of adamantoyl L-prolinamides have been synthesized. These compounds have been found to be highly efficient organocatalysts for the Michael addition of aldehydes and ketones to nitroalkenes. Under the optimized reaction conditions, the corresponding Michael adducts were obtained in good yields (up to 95%), excellent enantioselectivities (up to 99% ee) and moderate diastereoselectivities.

  已经合成了一系列的金刚烷基L-脯氨酰胺。已经发现这些化合物是用于将醛和酮迈克尔加成至硝基烯烃的高效有机催化剂。在优化的反应条件下，以高收率（最高95％），优异的对映选择性（最高99％ee）和中等非对映选择性获得了相应的迈克尔加合物。
• Synthesis of <i>N</i>-alkylated lipopeptides and their application as organocatalysts in asymmetric Michael addition in aqueous environments
  作者：José A. C. Delgado、Fidel E. M. Vicente、Alexander F. de la Torre、Vitor A. Fernandes、Arlene G. Corrêa、Márcio W. Paixão

  DOI：10.1039/d1nj01112j

  日期：——

  through an isocyanide-based multicomponent reaction. Various structural motifs were tunably introduced on the catalyst backbone with the aim of incorporating amphiphilic features. Consequently, they have further been evaluated in the 1,4-addition of aldehydes to trans-β-nitrostyrene having water as the sole solvent. Under sustainable reaction conditions, Michael adducts were obtained in excellent yields

  通过基于异氰化物的多组分反应合成了N-烷基化脂肽有机催化剂库。各种结构基序被可调地引入到催化剂骨架上，目的是结合两亲性特征。因此，它们已在醛与反式-β-硝基苯乙烯的 1,4-加成反应中得到进一步评估，其中水作为唯一溶剂。在可持续的反应条件下，迈克尔加合物以优异的产率、非对映选择性和对映选择性获得，使用低催化剂负载量且无添加剂。
• Aromatic l-prolinamide-catalyzed asymmetric Michael addition of aldehydes to nitroalkenes
  作者：Yongchao Wang、Jun Lin、Kun Wei

  DOI：10.1016/j.tetasy.2014.11.006

  日期：2014.12

  Two chiral aromatic L-prolinamides were synthesized in high overall yield (95%) from N-Boc-L-proline and served as organocatalysts in asymmetric Michael reactions of aldehydes to nitroalkenes. Under the optimized reaction conditions, (S)-N-tritylpyrrolidine-2-carboxamide 4 was found to be a highly efficient organocatalyst for the Michael addition, and the corresponding Michael adducts were obtained in good yields (up to 94%), with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to 99:1 dr). (C) 2014 Elsevier Ltd. All rights reserved.