(1R,2R)-N,N'-di(2',3',4',5',6'-pentafluorobenzyl)-1,2-diaminocyclohexane

• 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: (1R,2R)-N,N'-di(2',3',4',5',6'-pentafluorobenzyl)-1,2-diaminocyclohexane
• 英文别名: (1R,2R)-1-N,2-N-bis[(2,3,4,5,6-pentafluorophenyl)methyl]cyclohexane-1,2-diamine
• 化学式: C₂₀H₁₆F₁₀N₂
• 分子量: 474.344
• InChiKey: ZZBNTMVIJHFSKX-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (1R,2R)-N,N'-di(2',3',4',5',6'-pentafluorobenzylidene)-1,2-diaminocyclohexane 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以50%的产率得到(1R,2R)-N,N'-di(2',3',4',5',6'-pentafluorobenzyl)-1,2-diaminocyclohexane
  参考文献：
  名称：

  Chiral hybrid silica: sol–gel heterogenisation of trans-(1R,2R)-diaminocyclohexane ligands for the rhodium catalysed enantioselective reduction of acetophenone

  摘要：

  The synthesis of derivatives of trans-(1R,2R)-diaminocyclohexane with different substituents on the nitrogen atoms has been achieved. Rhodium complexes of these chiral ligands were evaluated as homogeneous catalysts for the asymmetric hydride transfer reduction (HTR) of acetophenone leading to moderate selectivities (ee = 0-57%). The silylation of a bromo-aryl derivative was successfully performed by a Heck's coupling reaction with vinyltriethoxysilane in the presence of a palladium catalyst. The immobilisation of this catalyst was then achieved by the sol-gel hydrolysis condensation. The resulting hybrid catalytic materials showed moderate selectivity, although much higher than the related homogeneous catalytic species. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.005

文献信息

• Nickel-Catalyzed Asymmetric <i>C</i>-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides
  作者：Vijayarajan Devannah、Rajgopal Sharma、Donald A. Watson

  DOI：10.1021/jacs.9b04175

  日期：2019.5.29

  A general catalytic method for asymmetric C-alkylation of nitroalkanes using nickel catalysis is described. This method enables the formation of highly enantioenriched β-nitroamides from readily available α-bromoamides using mild reaction conditions that are compatible with a wide range of functional groups. When combined with subsequent reactions, this method allows access to highly enantioenriched

  描述了使用镍催化对硝基烷烃进行不对称 C-烷基化的一般催化方法。该方法能够使用与各种官能团兼容的温和反应条件，从容易获得的 α-溴酰胺形成高度对映体富集的 β-硝基酰胺。当与后续反应相结合时，该方法允许获得具有含氮完全取代的碳中心的高度对映体富集的产品。
• Chiral hybrid silica: sol–gel heterogenisation of trans-(1R,2R)-diaminocyclohexane ligands for the rhodium catalysed enantioselective reduction of acetophenone
  作者：Anne Brethon、Joël J.E Moreau、Michel Wong Chi Man

  DOI：10.1016/j.tetasy.2003.11.005

  日期：2004.2

  The synthesis of derivatives of trans-(1R,2R)-diaminocyclohexane with different substituents on the nitrogen atoms has been achieved. Rhodium complexes of these chiral ligands were evaluated as homogeneous catalysts for the asymmetric hydride transfer reduction (HTR) of acetophenone leading to moderate selectivities (ee = 0-57%). The silylation of a bromo-aryl derivative was successfully performed by a Heck's coupling reaction with vinyltriethoxysilane in the presence of a palladium catalyst. The immobilisation of this catalyst was then achieved by the sol-gel hydrolysis condensation. The resulting hybrid catalytic materials showed moderate selectivity, although much higher than the related homogeneous catalytic species. (C) 2003 Elsevier Ltd. All rights reserved.