(R)-1-bromo-2-(1-methoxymethoxy-1H-perfluorooctyl)benzene | 835624-47-0

• 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: (R)-1-bromo-2-(1-methoxymethoxy-1H-perfluorooctyl)benzene
• 英文别名: 1-bromo-2-[(1R)-2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-(methoxymethoxy)octyl]benzene
• CAS: 835624-47-0
• 化学式: C₁₆H₁₀BrF₁₅O₂
• 分子量: 599.134
• InChiKey: QXLKKWNFBHRCDI-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  (R)-1-bromo-2-(1-methoxymethoxy-1H-perfluorooctyl)benzene 在 bis(1,5-cyclooctadiene)nickel (0) 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (Ra)-2,2'-bis[(R)-1-hydroxy-1H-perfluorooctyl]-biphenyl
  参考文献：
  名称：

  New axially dissymmetric ligand recoverable with fluorous solvent

  摘要：

  Axially dissymmetric ligands with perfluoroalkyl groups, (Ra)-2,2'-bis[(R)-1-hydroxy-1H-perfluorooctyl]biphenyl [(Ra)-(R)(2)-1c] and its enantiomer, have been synthesized successfully by the coupling reaction of the corresponding aryl bromide using Ni(COD)(2). These ligands showed much higher asymmetric induction in the reaction of various aldehydes with diethylzinc than the trifluoromethyl (1a) or pentafluoroethyl (1b) analogues. Furthermore, 1c was recovered quantitatively by extraction with a fluorous solvent from the reaction mixture due to its high fluorine content. The recovered ligand 1c was pure enough to be reused without purification. The efficiency of 1c as the chiral ligand was not decreased at all even after seven times recycling (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.063
• 作为产物：
  描述：

  1-(2-bromophenyl)perfluorooctan-1-one 在 sodium hydride 、 (R)-2-甲基-CBS-恶唑硼烷 、 儿萘酚硼烷 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-1-bromo-2-(1-methoxymethoxy-1H-perfluorooctyl)benzene
  参考文献：
  名称：

  New axially dissymmetric ligand recoverable with fluorous solvent

  摘要：

  Axially dissymmetric ligands with perfluoroalkyl groups, (Ra)-2,2'-bis[(R)-1-hydroxy-1H-perfluorooctyl]biphenyl [(Ra)-(R)(2)-1c] and its enantiomer, have been synthesized successfully by the coupling reaction of the corresponding aryl bromide using Ni(COD)(2). These ligands showed much higher asymmetric induction in the reaction of various aldehydes with diethylzinc than the trifluoromethyl (1a) or pentafluoroethyl (1b) analogues. Furthermore, 1c was recovered quantitatively by extraction with a fluorous solvent from the reaction mixture due to its high fluorine content. The recovered ligand 1c was pure enough to be reused without purification. The efficiency of 1c as the chiral ligand was not decreased at all even after seven times recycling (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.063

文献信息

• Synthesis of new axially dissymmetric ligand with large perfluoroalkyl groups
  作者：Masaaki Omote、Yuji Nishimura、Kazuyuki Sato、Akira Ando、Itsumaro Kumadaki

  DOI：10.1016/j.tetlet.2004.11.038

  日期：2005.1

  A new axially dissymmetric ligand with large perfluoroalkyl groups, 2,2'-bis(1-hydroxy-1H-per-fluorooctyl)biphenyl(1c). which could not be obtained by the coupling reaction of the aryl bromide using copper powder, was synthesized successfully by the coupling reaction using Ni(COD)(2). This ligand showed much higher asymmetric induction in the reaction of diethylzinc with benzaldehyde than the trifluoromethyl (1a) or pentafluoroethyl (1b) analogues. (C) 2004 Elsevier Ltd. All rights reserved.
• New axially dissymmetric ligand recoverable with fluorous solvent
  作者：Masaaki Omote、Yuji Nishimura、Kazuyuki Sato、Akira Ando、Itsumaro Kumadaki

  DOI：10.1016/j.tet.2005.11.063

  日期：2006.2

  Axially dissymmetric ligands with perfluoroalkyl groups, (Ra)-2,2'-bis[(R)-1-hydroxy-1H-perfluorooctyl]biphenyl [(Ra)-(R)(2)-1c] and its enantiomer, have been synthesized successfully by the coupling reaction of the corresponding aryl bromide using Ni(COD)(2). These ligands showed much higher asymmetric induction in the reaction of various aldehydes with diethylzinc than the trifluoromethyl (1a) or pentafluoroethyl (1b) analogues. Furthermore, 1c was recovered quantitatively by extraction with a fluorous solvent from the reaction mixture due to its high fluorine content. The recovered ligand 1c was pure enough to be reused without purification. The efficiency of 1c as the chiral ligand was not decreased at all even after seven times recycling (c) 2005 Elsevier Ltd. All rights reserved.