1-Bromo-8-(2,4,6-cycloheptatrien-1-yl)naphthalene | 70416-26-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1-Bromo-8-(2,4,6-cycloheptatrien-1-yl)naphthalene
• 英文别名: 1-Brom-8-(cyclohepta-2,4,6-trien-1-yl)-naphthalin；1-Bromo-8-cyclohepta-2,4,6-trien-1-ylnaphthalene
• CAS: 70416-26-1
• 化学式: C₁₇H₁₃Br
• 分子量: 297.194
• InChiKey: MRLAJSRGNBEUPU-UHFFFAOYSA-N

物化性质

• 沸点：
  424.0±14.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-Bromo-8-(2,4,6-cycloheptatrien-1-yl)naphthalene 、 2-naphthalenylmagnesium bromide 生成 1-(2-Naphthyl)-8-tropylionaphthalene Hexafluoroantimonate
  参考文献：
  名称：

  1-Naphthyltropylium ions having condensed aromatic rings at the 8-position: dependence of the intramolecular charge-transfer interaction upon geometry of the donor

  摘要：

  A series of 1-aryl-8-tropylionaphthalene cations (aryl = 1-naphthyl (8a), 2-naphthyl (8b), 1-pyrenyl (8c), and 2-pyrenyl (8d)) have been synthesized, in which the condensed aromatic system and a tropylium ring are placed at a face-to-face arrangement. The H-1 NMR spectra of these cations exhibit remarkable upfield shift for the tropylium ring protons in accord with such molecular geometry: this geometry is further supported by theoretical calculations both by MMP2 and AM1. The cations 8a-d show the intramolecular charge-transfer (CT) band at 510 (sh) (8a), 525 (sh) (8b), 585 (8c), and 600 (sh) nm (8d) in dichloromethane, indicating a correlation of the CT transition energy with the donor's ionization potential regardless of the relative geometry with the acceptor. In contrast, the indices of cation's thermodynamic stability, pK(R+) (6.27 for 8a, 5.45 for 8b, 6.28 for 8c, and 5.75 for 8d), and reduction potential (-0.649 V vs Ag/Ag+ for 8a, -0.601 for 8b, -0.665 for 8c, and -0.625 V for 8d) are highly dependent on the mutual geometry of donor and acceptor, reflecting the effectiveness in overlap of donor's HOMO and acceptor's LUMO.

  DOI：

  10.1021/jo00028a043
• 作为产物：
  描述：

  1,8-二溴萘 、 tropylium tetrafluoroborate 生成 1-Bromo-8-(2,4,6-cycloheptatrien-1-yl)naphthalene
  参考文献：
  名称：

  1-Aryl-8-tropylionaphthalene perchlorates: synthesis and intramolecular charge-transfer interaction

  摘要：

  DOI：

  10.1021/jo01329a024