[4-Tert-butyl-2-[5-tert-butyl-3-[5-tert-butyl-3-[5-tert-butyl-2-(trifluoromethylsulfonyloxy)phenyl]sulfanyl-2-hydroxyphenyl]sulfanyl-2-hydroxyphenyl]sulfanylphenyl] trifluoromethanesulfonate | 1293286-39-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: [4-Tert-butyl-2-[5-tert-butyl-3-[5-tert-butyl-3-[5-tert-butyl-2-(trifluoromethylsulfonyloxy)phenyl]sulfanyl-2-hydroxyphenyl]sulfanyl-2-hydroxyphenyl]sulfanylphenyl] trifluoromethanesulfonate
• 英文别名: [4-tert-butyl-2-[5-tert-butyl-3-[5-tert-butyl-3-[5-tert-butyl-2-(trifluoromethylsulfonyloxy)phenyl]sulfanyl-2-hydroxyphenyl]sulfanyl-2-hydroxyphenyl]sulfanylphenyl] trifluoromethanesulfonate
• CAS: 1293286-39-1
• 化学式: C₄₂H₄₈F₆O₈S₅
• 分子量: 955.159
• InChiKey: QTXMJQIKBDJQSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.6
• 重原子数：
  61
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  220
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  [4-Tert-butyl-2-[5-tert-butyl-3-[5-tert-butyl-3-[5-tert-butyl-2-(trifluoromethylsulfonyloxy)phenyl]sulfanyl-2-hydroxyphenyl]sulfanyl-2-hydroxyphenyl]sulfanylphenyl] trifluoromethanesulfonate 在 吡啶 、 palladium diacetate 、 N,N-二异丙基乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Synthesis of novel dihydroxydiphosphines and dihydroxydicarboxylic acids having a tetra(thio-1,3-phenylene-2-yl) backbone

  摘要：

  Novel tetradentate PPh2-OH hybrid ligands 5 and CO2H-OH hybrid ligands 6 have been successfully synthesised from tetra(thio-5-tert-butyl-2-hydroxy-1,3-phenylene) (24) by replacing the hydroxy groups at both the 2-position and either the 2'-, 2''- or 2'''-position with diphenylphosphino or carboxy groups, after converting into bistriflates 8; the substitution positions of newly introduced substituents are denoted hereafter by superscript 1,n as 51,n. Bistriflates 81,3 and 81,4 can be readily prepared by the regioselective detriflation of tetrakistriflate 7 with tetrabutylammonium fluoride (TBAF), conducted under different conditions. On the other hand, the preparation of bistriflate 81,2 requires a four-step process through protection/deprotection. Thus, the silylation of tetraol 24 with an excess of 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane gives O,O'- and O'',O'''-disiloxane-1,3-diyl-capped derivative 9. One of the two disiloxane bridges is removed by the treatment with 0.5mol equiv. of TBAF to give diol 10. Triflation of diol 10, followed by the removal of the remaining disiloxane bridge, affords bistriflate 81,2. Bistriflates 8 are subjected to palladium-catalysed phosphorylation, followed by the reduction of the resulting phosphine oxide 121,n to give PPh2-OH hybrid ligands 51,n (n=2-4), while CO2H-OH hybrid ligands 61,n (n=3,4) are obtained from 8 via acetylation of the remaining hydroxy groups, followed by palladium-catalysed methoxycarbonylation of the TfO moieties, and subsequent hydrolysis of the resulting tetraesters 14. X-ray structural analyses of dicarboxylic acids 61,3 and 61,4 reveal that they form quite different 3D network structures to each other. Interestingly, 61,4 constructs a porous channel with a potential for serving as a supramolecular host, by the stacking of its cyclic dimer that is formed by intermolecular hydrogen bondings between the carboxy groups.

  DOI：

  10.1080/10610278.2010.514913
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以56%的产率得到[4-Tert-butyl-2-[5-tert-butyl-3-[5-tert-butyl-3-[5-tert-butyl-2-(trifluoromethylsulfonyloxy)phenyl]sulfanyl-2-hydroxyphenyl]sulfanyl-2-hydroxyphenyl]sulfanylphenyl] trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of novel dihydroxydiphosphines and dihydroxydicarboxylic acids having a tetra(thio-1,3-phenylene-2-yl) backbone

  摘要：

  Novel tetradentate PPh2-OH hybrid ligands 5 and CO2H-OH hybrid ligands 6 have been successfully synthesised from tetra(thio-5-tert-butyl-2-hydroxy-1,3-phenylene) (24) by replacing the hydroxy groups at both the 2-position and either the 2'-, 2''- or 2'''-position with diphenylphosphino or carboxy groups, after converting into bistriflates 8; the substitution positions of newly introduced substituents are denoted hereafter by superscript 1,n as 51,n. Bistriflates 81,3 and 81,4 can be readily prepared by the regioselective detriflation of tetrakistriflate 7 with tetrabutylammonium fluoride (TBAF), conducted under different conditions. On the other hand, the preparation of bistriflate 81,2 requires a four-step process through protection/deprotection. Thus, the silylation of tetraol 24 with an excess of 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane gives O,O'- and O'',O'''-disiloxane-1,3-diyl-capped derivative 9. One of the two disiloxane bridges is removed by the treatment with 0.5mol equiv. of TBAF to give diol 10. Triflation of diol 10, followed by the removal of the remaining disiloxane bridge, affords bistriflate 81,2. Bistriflates 8 are subjected to palladium-catalysed phosphorylation, followed by the reduction of the resulting phosphine oxide 121,n to give PPh2-OH hybrid ligands 51,n (n=2-4), while CO2H-OH hybrid ligands 61,n (n=3,4) are obtained from 8 via acetylation of the remaining hydroxy groups, followed by palladium-catalysed methoxycarbonylation of the TfO moieties, and subsequent hydrolysis of the resulting tetraesters 14. X-ray structural analyses of dicarboxylic acids 61,3 and 61,4 reveal that they form quite different 3D network structures to each other. Interestingly, 61,4 constructs a porous channel with a potential for serving as a supramolecular host, by the stacking of its cyclic dimer that is formed by intermolecular hydrogen bondings between the carboxy groups.

  DOI：

  10.1080/10610278.2010.514913

文献信息

• Synthesis of novel dihydroxydiphosphines and dihydroxydicarboxylic acids having a tetra(thio-1,3-phenylene-2-yl) backbone
  作者：Yuki Akahira、Kazutoshi Nagata、Naoya Morohashi、Tetsutaro Hattori

  DOI：10.1080/10610278.2010.514913

  日期：2011.1.1

  Novel tetradentate PPh2-OH hybrid ligands 5 and CO2H-OH hybrid ligands 6 have been successfully synthesised from tetra(thio-5-tert-butyl-2-hydroxy-1,3-phenylene) (24) by replacing the hydroxy groups at both the 2-position and either the 2'-, 2''- or 2'''-position with diphenylphosphino or carboxy groups, after converting into bistriflates 8; the substitution positions of newly introduced substituents are denoted hereafter by superscript 1,n as 51,n. Bistriflates 81,3 and 81,4 can be readily prepared by the regioselective detriflation of tetrakistriflate 7 with tetrabutylammonium fluoride (TBAF), conducted under different conditions. On the other hand, the preparation of bistriflate 81,2 requires a four-step process through protection/deprotection. Thus, the silylation of tetraol 24 with an excess of 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane gives O,O'- and O'',O'''-disiloxane-1,3-diyl-capped derivative 9. One of the two disiloxane bridges is removed by the treatment with 0.5mol equiv. of TBAF to give diol 10. Triflation of diol 10, followed by the removal of the remaining disiloxane bridge, affords bistriflate 81,2. Bistriflates 8 are subjected to palladium-catalysed phosphorylation, followed by the reduction of the resulting phosphine oxide 121,n to give PPh2-OH hybrid ligands 51,n (n=2-4), while CO2H-OH hybrid ligands 61,n (n=3,4) are obtained from 8 via acetylation of the remaining hydroxy groups, followed by palladium-catalysed methoxycarbonylation of the TfO moieties, and subsequent hydrolysis of the resulting tetraesters 14. X-ray structural analyses of dicarboxylic acids 61,3 and 61,4 reveal that they form quite different 3D network structures to each other. Interestingly, 61,4 constructs a porous channel with a potential for serving as a supramolecular host, by the stacking of its cyclic dimer that is formed by intermolecular hydrogen bondings between the carboxy groups.