1-bromo-3,5,7-tris(methoxycarbonyl)adamantane | 879687-44-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-bromo-3,5,7-tris(methoxycarbonyl)adamantane
• 英文别名: Trimethyl 7-bromoadamantane-1,3,5-tricarboxylate
• CAS: 879687-44-2
• 化学式: C₁₆H₂₁BrO₆
• 分子量: 389.243
• InChiKey: NSOJAWUPQPGFJY-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C
• 沸点：
  417.3±45.0 °C(Predicted)
• 密度：
  1.584±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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 95.5h， 生成 1-phenyl-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
• 作为产物：
  描述：

  、 甲醇 反应 3.0h， 以2.17 g的产率得到1-bromo-3,5,7-tris(methoxycarbonyl)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

• Tuning the coverage of self-assembled monolayer by introducing bulky substituents onto rigid adamantane tripod
  作者：Toshikazu Kitagawa、Shima Nakanishi、Aya Mizuno、Yohei Niwa、Hiroaki Tabata、Katsuyuki Hirai、Takao Okazaki

  DOI：10.24820/ark.5550190.p010.356

  日期：——

  An area-demanding tripodal trithiol containing six peripheral methyl groups was synthesized, and its selfassembled monolayer (SAM) was formed onto a Au(111) surface, which was electrochemically characterized. The SAM showed a significant lowering of the surface coverage due to the bulkiness of the methyl groups, as demonstrated by the charge of reductive elimination. The experimentally determined surface

  合成了包含六个外围甲基的面积要求高的三足三硫醇，并将其自组装单分子层 (SAM) 形成在 Au(111) 表面上，并对其进行了电化学表征。正如还原消除电荷所证明的那样，由于甲基的体积大，SAM 显示出表面覆盖率的显着降低。在周期性边界条件下，通过密度泛函理论 (DFT) 计算恰当地再现了实验确定的表面密度。
• 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.