(2R,3R)-1,4-bis(1H,1H,2H,2H,3H,3H-perfluoroundecyloxy)butane-2,3-diamine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-1,4-bis(1H,1H,2H,2H,3H,3H-perfluoroundecyloxy)butane-2,3-diamine
• 英文别名: (2R,3R)-1,4-bis(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecoxy)butane-2,3-diamine
• 化学式: C₂₆H₂₂F₃₄N₂O₂
• 分子量: 1040.42
• InChiKey: IUQZHUQNYSLIKE-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  64
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  38

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1,4-bis(1H,1H,2H,2H,3H,3H-perfluoroundecyloxy)butane-2,3-diamine 、 3,5-bis(n-heptadecafluorooctyl)benzaldehyde 以 乙醇 为溶剂， 反应 6.0h， 以61%的产率得到(2R,3R)-N,N-bis{(1E)-[3,5-bis(perfluorooctl)phenyl]methylene}-1,4-bis(1H,1H,2H,2H,3H,3H-perfluoroundecyloxy)butane-2,3-diamine
  参考文献：
  名称：

  Enantiopure fluorous amino-derivatives: synthesis and some applications in asymmetric organometallic catalysis

  摘要：

  The preparation of (2R,3R)-1,4-bis[(1H,1H,2H,2H,3H,3H-perfluoroundecyl)oxy]butane-2,3-diol 5 from (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol is described. This fluorous diol 5 can be easily converted to the corresponding fluorous enantiopure diamine 8 and amino alcohol 12. While diamine 8 afforded fluorous diimine 9, amino alcohol 12 is the precursor of imino alcohol 13 and amino alcohol 14. Enantioselectivities of up to 31% were obtained in the reduction of acetophenone using iridium or ruthenium complexes associated with these compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.008
• 作为产物：
  描述：

  全氟辛基碘烷 在 palladium on activated charcoal 盐酸 、 sodium azide 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 80.0h， 生成 (2R,3R)-1,4-bis(1H,1H,2H,2H,3H,3H-perfluoroundecyloxy)butane-2,3-diamine
  参考文献：
  名称：

  Enantiopure fluorous amino-derivatives: synthesis and some applications in asymmetric organometallic catalysis

  摘要：

  The preparation of (2R,3R)-1,4-bis[(1H,1H,2H,2H,3H,3H-perfluoroundecyl)oxy]butane-2,3-diol 5 from (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol is described. This fluorous diol 5 can be easily converted to the corresponding fluorous enantiopure diamine 8 and amino alcohol 12. While diamine 8 afforded fluorous diimine 9, amino alcohol 12 is the precursor of imino alcohol 13 and amino alcohol 14. Enantioselectivities of up to 31% were obtained in the reduction of acetophenone using iridium or ruthenium complexes associated with these compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.008

文献信息

• Enantiopure fluorous amino-derivatives: synthesis and some applications in asymmetric organometallic catalysis
  作者：Jerome Bayardon、David Maillard、Gianluca Pozzi、Denis Sinou

  DOI：10.1016/j.tetasy.2004.07.008

  日期：2004.9

  The preparation of (2R,3R)-1,4-bis[(1H,1H,2H,2H,3H,3H-perfluoroundecyl)oxy]butane-2,3-diol 5 from (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol is described. This fluorous diol 5 can be easily converted to the corresponding fluorous enantiopure diamine 8 and amino alcohol 12. While diamine 8 afforded fluorous diimine 9, amino alcohol 12 is the precursor of imino alcohol 13 and amino alcohol 14. Enantioselectivities of up to 31% were obtained in the reduction of acetophenone using iridium or ruthenium complexes associated with these compounds. (C) 2004 Elsevier Ltd. All rights reserved.