3,5-bis(n-heptadecafluorooctyl)benzaldehyde

• 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: 3,5-bis(n-heptadecafluorooctyl)benzaldehyde
• 英文别名: 3,5-bis(n-perfluorooctyl)benzaldehyde；3,5-Bis(perfluorooctyl)benzaldehyde；3,5-Bis(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)benzaldehyde
• 化学式: C₂₃H₄F₃₄O
• 分子量: 942.23
• InChiKey: UUQDDOHSCFVWFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  58
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  35

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：

  3,5-二溴苯甲酸甲酯 在 lithium aluminium tetrahydride 、 铜 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 59.0h， 生成 3,5-bis(n-heptadecafluorooctyl)benzaldehyde
  参考文献：
  名称：

  亲氟分子的改进设计：使用3D QSAR描述符和神经网络预测ln P氟分配系数，亲氟性

  摘要：

  3D QSAR分子描述符和人工神经网络的组合已用于预测各种部分氟化有机化合物的亲氟性，即全氟（甲基环己烷）/甲苯分配系数的自然对数。预测的平均误差小于0.2实验误差的两倍。多元线性回归证明效率低得多。为了更好地表征氟分配现象，将特定的氟定义为氟的亲和性以及被排出的氟溶剂与进入的溶质分子的范德华体积比的乘积。这个无量纲的术语在化合物家族中与所计算的氟分子的希尔德布兰德参数具有很好的相关性。

  DOI：

  10.1016/s0022-1139(01)00342-6

文献信息

• Fluorous Biphasic Catalytic Oxidation of Sulfides by Molecular Oxygen/2,2-Dimethylpropanal
  作者：Stefano Colonna、Nicoletta Gaggero、Fernando Montanari、Gianluca Pozzi、Silvio Quici

  DOI：10.1002/1099-0690(200101)2001:1<181::aid-ejoc181>3.0.co;2-3

  日期：2001.1

  The use of perfluoroalkyl-substituted cobalt complexes as catalysts for the oxidation of alkyl aryl sulfides with molecular oxygen/2,2-dimethypropanal has been studied in a fluorous organic biphasic system. The addition of very small amounts of a CoII−tetraarylporphyrin (Co-4) led to increased substrate conversions (67−100%). Sulfoxide was generally obtained as the main product, together with variable

  在氟有机双相体系中，已经研究了使用全氟烷基取代的钴络合物作为催化剂用分子氧/ 2,2-二甲基丙醛氧化烷基芳基硫醚的方法。添加非常少量的Co II-四芳基卟啉（Co- 4）导致底物转化率提高（67-100％）。通常会获得亚砜作为主要产物，并根据基材的性质而获得不同数量的砜（0-100％）。全氟烷基取代的Co II-酞菁（Co- 6）被证明对底物转化效率较低（40-78％），但选择性地提供了亚砜。尽管尚未详细研究其机理，但该反应可能通过Co II配合物引发的自由基氧化过程进行。由于催化剂在反应条件下的不稳定性，通过相分离回收催化剂的尝试在一定程度上是无效的，这在Co- 6的情况下更为明显。
• Asymmetric hydrogen transfer reduction of ketones using chiral perfluorinated diimines and diamines
  作者：David Maillard、Gianluca Pozzi、Silvio Quici、Denis Sinou

  DOI：10.1016/s0040-4020(02)00247-8

  日期：2002.5

  Hydrogen transfer reduction of various ketones occurs in a mixture of perfluoroalkane/isopropanol using iridium complexes in association with chiral perfluorinated diimines or diamines as ligands. Enantioselectivity of up to 79% has been obtained. Recycling of the catalyst using chiral perfluorinated diamines as the ligands is possible with no loss of enantioselectivity and very low leaching of iridium in the organic phase. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.
• An improved design of fluorophilic molecules: prediction of the ln P fluorous partition coefficient, fluorophilicity, using 3D QSAR descriptors and neural networks
  作者：László E. Kiss、István Kövesdi、József Rábai

  DOI：10.1016/s0022-1139(01)00342-6

  日期：2001.3

  entering solute molecules. This dimensionless term correlates well in a compound family with the calculated Hildebrand parameters of the fluorous molecules. The trifluoromethyl group was found highly effective for increasing the fluorous phase affinities of model compounds when used in combination with longer perfluoroalkyl groups.

  3D QSAR分子描述符和人工神经网络的组合已用于预测各种部分氟化有机化合物的亲氟性，即全氟（甲基环己烷）/甲苯分配系数的自然对数。预测的平均误差小于0.2实验误差的两倍。多元线性回归证明效率低得多。为了更好地表征氟分配现象，将特定的氟定义为氟的亲和性以及被排出的氟溶剂与进入的溶质分子的范德华体积比的乘积。这个无量纲的术语在化合物家族中与所计算的氟分子的希尔德布兰德参数具有很好的相关性。