1-(4-bromophenyl)-3,5,7-tris[(trifluoromethylsulfonyloxy)methyl]adamantane | 879687-52-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1-(4-bromophenyl)-3,5,7-tris[(trifluoromethylsulfonyloxy)methyl]adamantane
• 英文别名: [3-(4-Bromophenyl)-5,7-bis(trifluoromethylsulfonyloxymethyl)-1-adamantyl]methyl trifluoromethanesulfonate
• CAS: 879687-52-2
• 化学式: C₂₂H₂₂BrF₉O₉S₃
• 分子量: 777.499
• InChiKey: KIXFANDRAVKIKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  155
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-3,5,7-tris[(trifluoromethylsulfonyloxy)methyl]adamantane 在 氢氧化钾 、 18-冠醚-6 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 4.0h， 生成 1-(4-bromophenyl)-3,5,7-tris(mercaptomethyl)adamantane
  参考文献：
  名称：

  Rigid Molecular Tripod with an Adamantane Framework and Thiol Legs. Synthesis and Observation of an Ordered Monolayer on Au(111)

  摘要：

  Tripod-shaped trithiols 1-3, containing CH2SH groups at the three bridgehead positions of the adamantane framework and a halogen-containing group [Br (1), p-BrC6H4 (2), or p-IC6H4 (3)] at the fourth bridgehead, were synthesized, and self-assembled monolayers (SAMs) were prepared on atomically flat Au(111) surfaces. The three-point chemisorption of these tripods was confirmed by polarization modulation infrared reflection absorption spectroscopy, which showed the absence of a S-H stretching band. Scanning tunneling microscopy of the SAM of 1 exhibited a hexagonal arrangement of the adsorbed molecule with a lattice constant of 8.7 angstrom. A unidirectionally oriented, head-to-tail array of 1, which allows the close approach of neighboring molecules, is proposed as a reasonable model of the two-dimensional crystal, where the adsorbed sulfur atoms form a quasi-(root 3 x root 3)R30 degrees lattice. The charge of the electrochemical reductive desorption of the SAM of 1 was in good agreement with the expected surface coverage, while the SAMs of 2 and 3 showed somewhat less (ca. 70%) charge. The large negative reduction peak potentials, observed for the SAM of 1, are taken to indicate a tight anchoring of this tripod by three sulfur atoms.

  DOI：

  10.1021/jo051863j
• 作为产物：
  描述：

  1-bromo-3,5,7-tris(methoxycarbonyl)adamantane 在 吡啶 、 silver hexafluoroantimonate 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 1-(4-bromophenyl)-3,5,7-tris[(trifluoromethylsulfonyloxy)methyl]adamantane
  参考文献：
  名称：

  Rigid Molecular Tripod with an Adamantane Framework and Thiol Legs. Synthesis and Observation of an Ordered Monolayer on Au(111)

  摘要：

  Tripod-shaped trithiols 1-3, containing CH2SH groups at the three bridgehead positions of the adamantane framework and a halogen-containing group [Br (1), p-BrC6H4 (2), or p-IC6H4 (3)] at the fourth bridgehead, were synthesized, and self-assembled monolayers (SAMs) were prepared on atomically flat Au(111) surfaces. The three-point chemisorption of these tripods was confirmed by polarization modulation infrared reflection absorption spectroscopy, which showed the absence of a S-H stretching band. Scanning tunneling microscopy of the SAM of 1 exhibited a hexagonal arrangement of the adsorbed molecule with a lattice constant of 8.7 angstrom. A unidirectionally oriented, head-to-tail array of 1, which allows the close approach of neighboring molecules, is proposed as a reasonable model of the two-dimensional crystal, where the adsorbed sulfur atoms form a quasi-(root 3 x root 3)R30 degrees lattice. The charge of the electrochemical reductive desorption of the SAM of 1 was in good agreement with the expected surface coverage, while the SAMs of 2 and 3 showed somewhat less (ca. 70%) charge. The large negative reduction peak potentials, observed for the SAM of 1, are taken to indicate a tight anchoring of this tripod by three sulfur atoms.

  DOI：

  10.1021/jo051863j

文献信息

• Rigid Molecular Tripod with an Adamantane Framework and Thiol Legs. Synthesis and Observation of an Ordered Monolayer on Au(111)
  作者：Toshikazu Kitagawa、Yuichi Idomoto、Hiroaki Matsubara、Daisuke Hobara、Takashi Kakiuchi、Takao Okazaki、Koichi Komatsu

  DOI：10.1021/jo051863j

  日期：2006.2.1

  Tripod-shaped trithiols 1-3, containing CH2SH groups at the three bridgehead positions of the adamantane framework and a halogen-containing group [Br (1), p-BrC6H4 (2), or p-IC6H4 (3)] at the fourth bridgehead, were synthesized, and self-assembled monolayers (SAMs) were prepared on atomically flat Au(111) surfaces. The three-point chemisorption of these tripods was confirmed by polarization modulation infrared reflection absorption spectroscopy, which showed the absence of a S-H stretching band. Scanning tunneling microscopy of the SAM of 1 exhibited a hexagonal arrangement of the adsorbed molecule with a lattice constant of 8.7 angstrom. A unidirectionally oriented, head-to-tail array of 1, which allows the close approach of neighboring molecules, is proposed as a reasonable model of the two-dimensional crystal, where the adsorbed sulfur atoms form a quasi-(root 3 x root 3)R30 degrees lattice. The charge of the electrochemical reductive desorption of the SAM of 1 was in good agreement with the expected surface coverage, while the SAMs of 2 and 3 showed somewhat less (ca. 70%) charge. The large negative reduction peak potentials, observed for the SAM of 1, are taken to indicate a tight anchoring of this tripod by three sulfur atoms.