(R)-6,6'-bis(1H,1H,2H,2H-perfluoro-1-octyl)-2,2'-dihydroxy-1,1'-binaphthyl | 359699-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-6,6'-bis(1H,1H,2H,2H-perfluoro-1-octyl)-2,2'-dihydroxy-1,1'-binaphthyl
• 英文别名: (R)-6,6'-bis(1H,1H,2H,2H-perfluorooctyl)-2,2'-dihydroxy-1,1'-binaphthyl；1-[2-Hydroxy-6-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)naphthalen-1-yl]-6-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)naphthalen-2-ol
• CAS: 359699-85-7
• 化学式: C₃₆H₂₀F₂₆O₂
• 分子量: 978.512
• InChiKey: QWFJRWSIBWGXRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.5
• 重原子数：
  64
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  (R)-6,6'-bis(1H,1H,2H,2H-perfluoro-1-octyl)-2,2'-dihydroxy-1,1'-binaphthyl 在 吡啶 、 三乙烯二胺 、 1,2-双(二苯基膦)乙烷氯化镍 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 (R)-6,6'-bis(1H,1H,2H,2H-perfluoro-1-octyl)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl
  参考文献：
  名称：

  Synthesis of fluoroalkyl-derivatised BINAP ligands

  摘要：

  Fluoroalkyl-derivatised R-BINAP ligands have been prepared, characterised and applied in the ruthenium-catalysed asymmetric hydrogenation of dimethyl itaconate, (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01835-4
• 作为产物：
  描述：

  1H,1H,2H-全氟-1-辛烯 在 palladium on activated charcoal 、 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) 氢气 、 sodium acetate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~125.0 ℃ 、3.0 MPa 条件下， 反应 24.0h， 生成 (R)-6,6'-bis(1H,1H,2H,2H-perfluoro-1-octyl)-2,2'-dihydroxy-1,1'-binaphthyl
  参考文献：
  名称：

  A general method to fluorous ponytail-substituted aromatics

  摘要：

  Palladium-catalyzed olefination of aryl halides led to a variety of fluorous ponytail-substituted, functionalized aryl compounds with good to excellent yields. The same chemistry was also applied to the synthesis of binaphathols bearing fluorinated ponytails. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00714-6

文献信息

• Asymmetric Aza-MoritaBaylisHillman Reaction ofN-Sulfonated Imines with Methyl Vinyl Ketone Catalyzed by Chiral Phosphine Lewis Bases Bearing Perfluoroalkanes as “Pony Tails”
  作者：Min Shi、Lian-Hui Chen、Wen-Dong Teng

  DOI：10.1002/adsc.200505123

  日期：2005.11

  In the aza-Morita–BaylisHillman reaction of N-sulfonated imines (N-arylmethylidene-4-methylbenzenesulfonamides and others) with methyl vinyl ketone (MVK), we found that in the presence of a catalytic amount of the chiral phosphine Lewis bases (R)-(−)-6,6′-bis[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]-2′-(diphenylphosphanyl)-[1,1′]binaphthalenyl-2-ol LB2 and (R)-(−)-6,6′-(3,3,4,4,5, 5

  在的氮杂森田-BaylisHillman反应Ñ -sulfonated亚胺（Ñ用甲基乙烯基酮（MVK）-arylmethylidene -4- methylbenzenesulfonamides等），我们发现，在手性膦路易斯碱催化量存在（ř）-（-）-6,6'-双[三（3,3,4,4,5,5,6,6,7,7,8,8,8,8-三氟氟辛基）甲硅烷基] -2'-（二苯基膦基）-[1,1']联萘-2-醇LB2和（R）-（-）-6,6'-（3,3,4,4,5，5,6,6,7,7， 8,8,8-三氟氟辛基）-2'-（二苯基膦基）-[1,1']联萘-2-醇LB3在萘骨架的6,6'-位带有两个全氟烷烃链，可以在室温（15°C）或低温（-分别在THF中（20°C）。LB3在该反应中比先前报道的原始手性膦路易斯碱（R）-（-）-2'-二苯基膦基-[1,1']二萘基-2-醇LB1更有效。
• A general method to fluorous ponytail-substituted aromatics
  作者：Weiping Chen、Lijin Xu、Jianliang Xiao

  DOI：10.1016/s0040-4039(01)00714-6

  日期：2001.6

  Palladium-catalyzed olefination of aryl halides led to a variety of fluorous ponytail-substituted, functionalized aryl compounds with good to excellent yields. The same chemistry was also applied to the synthesis of binaphathols bearing fluorinated ponytails. (C) 2001 Elsevier Science Ltd. All rights reserved.
• New approaches to fluorinated ligands and their application in catalysis
  作者：Weiping Chen、Lijin Xu、Yulai Hu、Anna M Banet Osuna、Jianliang Xiao

  DOI：10.1016/s0040-4020(02)00213-2

  日期：2002.5

  Simple and generic approaches to fluorous soluble ligands have been developed and applied to the synthesis of various fluorinated arylphosphines including polymeric ones. The utility of some of these ligands has been demonstrated in catalysis in supercritical CO2 (scCO(2)) and fluorous solvents. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of fluoroalkyl-derivatised BINAP ligands
  作者：David J Birdsall、Eric G Hope、Alison M Stuart、Weiping Chen、Yulai Hu、Jianliang Xiao

  DOI：10.1016/s0040-4039(01)01835-4

  日期：2001.11

  Fluoroalkyl-derivatised R-BINAP ligands have been prepared, characterised and applied in the ruthenium-catalysed asymmetric hydrogenation of dimethyl itaconate, (C) 2001 Elsevier Science Ltd. All rights reserved.