tert-butyl (1R,2S)-2-nitro-1-(4-(trifluoromethyl)phenyl)propylcarbamate

• 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: tert-butyl (1R,2S)-2-nitro-1-(4-(trifluoromethyl)phenyl)propylcarbamate
• 英文别名: [(R)-alpha-[(S)-1-Nitroethyl]-4-(trifluoromethyl)benzyl]carbamic acid tert-butyl ester；tert-butyl N-[(1R,2S)-2-nitro-1-[4-(trifluoromethyl)phenyl]propyl]carbamate
• 化学式: C₁₅H₁₉F₃N₂O₄
• 分子量: 348.322
• InChiKey: ZOEKUOZRCXAATM-CABZTGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tert-butyl 4-(trifluoromethyl)benzylidenecarbamate 、 硝基乙烷 在 N-((1R,2R)-2-(3-((1R,2R)-2-(dimethylamino)cyclohexyl)thioureido)-1,2-diphenylethyl)-3,5-bis(trifluoromethyl)benzenesulfonamide 作用下， 以 乙腈 为溶剂， 以97%的产率得到tert-butyl (1R,2S)-2-nitro-1-(4-(trifluoromethyl)phenyl)propylcarbamate
  参考文献：
  名称：

  Highly anti-Selective Asymmetric Nitro-Mannich Reactions Catalyzed by Bifunctional Amine-Thiourea-Bearing Multiple Hydrogen-Bonding Donors

  摘要：

  Highly anti-selective and enantioselective nitro-Mannich reactions have been achieved for a broad spectrum of substrates catalyzed by chiral bifunctional multiple hydrogen-bonding-donor amine-thioureas. Multiple hydrogen-bonding donors play a significant role in accelerating reactions and improving yields, diastereoselectivities, and enantioselectivities.

  DOI：

  10.1021/ja803538x

文献信息

• Enantioselective Aza-Henry Reaction with an <i>N</i>-Sulfinyl Urea Organocatalyst
  作者：MaryAnn T. Robak、Monica Trincado、Jonathan A. Ellman

  DOI：10.1021/ja075653v

  日期：2007.12.1

  simultaneously acidify the urea and provide asymmetric induction in hydrogen-bond-catalyzed reactions. The utility of this new catalyst structure is demonstrated by the high selectivity provided in the aza-Henry reaction not only for aromatic N-Boc imine substrates but also for aliphatic imines for which enantioselective H-bonding catalysis has not previously been demonstrated.

  已经开发出一类新的有机催化剂，它结合了亚磺酰基作为脲或硫脲取代基。亚磺酰基同时用于酸化尿素并在氢键催化反应中提供不对称诱导。这种新催化剂结构的实用性通过 aza-Henry 反应提供的高选择性得到证明，不仅对芳香族 N-Boc 亚胺底物，而且对脂肪族亚胺（之前尚未证明对映选择性氢键催化）。
• Chiral Proton Catalysis:  A Catalytic Enantioselective Direct Aza-Henry Reaction
  作者：Benjamin M. Nugent、Ryan A. Yoder、Jeffrey N. Johnston

  DOI：10.1021/ja031906i

  日期：2004.3.1

  during an enantioselective reaction, this work represents the first example of this phenomenon outside of a protein. A chiral, nonracemic BisAMidine (BAM) ligand was designed, synthesized, and complexed to the proton of a Brønsted acid. The resulting coordination compound catalyzed the production of enantioenriched product from the combination of a Schiff base and nitroalkane (the aza-Henry reaction). This

  尽管大自然长期以来一直能够使用质子（最普遍的路易斯酸）在对映选择性反应期间激活和定向底物，但这项工作代表了蛋白质之外这种现象的第一个例子。设计、合成了手性、非外消旋双脒 (BAM) 配体，并与布朗斯台德酸的质子络合。所得配位化合物催化席夫碱和硝基烷烃（氮杂-亨利反应）结合生成对映体富集的产物。这种特殊的反应也被认为是许多由酶催化的类似碳-碳键形成反应的模型（例如，曼尼希反应）。这一发现表明在不对称催化中使用离子氢键可能不仅比以前认为的更普遍，而且是一种可行的“
• Catalytic Asymmetric Nitro-Mannich Reactions with a Yb/K Heterobimetallic Catalyst
  作者：Tatsuya Nitabaru、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.3390/molecules15031280

  日期：——

  A catalytic asymmetric nitro-Mannich (aza-Henry) reaction with rare earth metal/alkali metal heterobimetallic catalysts is described. A Yb/K heterobimetallic catalyst assembled by an amide-based ligand promoted the asymmetric nitro-Mannich reaction to afford enantioenriched anti-b-nitroamines in up to 86% ee. Facile reduction of the nitro functionality allowed for efficient access to optically active

  描述了与稀土金属/碱金属异双金属催化剂的催化不对称硝基-曼尼希 (氮杂-亨利) 反应。由基于酰胺的配体组装的 Yb/K 杂双金属催化剂促进了不对称硝基-曼尼希反应，以提供高达 86% ee 的对映体富集的抗 b-硝基胺。硝基官能团的轻松还原允许有效获取光学活性 1,2-二胺。
• Highly <i>anti</i>-Selective Asymmetric Nitro-Mannich Reactions Catalyzed by Bifunctional Amine-Thiourea-Bearing Multiple Hydrogen-Bonding Donors
  作者：Chun-Jiang Wang、Xiu-Qin Dong、Zhi-Hai Zhang、Zhi-Yong Xue、Huai-Long Teng

  DOI：10.1021/ja803538x

  日期：2008.7.1

  Highly anti-selective and enantioselective nitro-Mannich reactions have been achieved for a broad spectrum of substrates catalyzed by chiral bifunctional multiple hydrogen-bonding-donor amine-thioureas. Multiple hydrogen-bonding donors play a significant role in accelerating reactions and improving yields, diastereoselectivities, and enantioselectivities.