1,8-bis(dimethylamino)-2-(4-methoxyphenyl)naphthalene | 1394231-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,8-bis(dimethylamino)-2-(4-methoxyphenyl)naphthalene
• 英文别名: 2-(4-methoxyphenyl)-1-N,1-N,8-N,8-N-tetramethylnaphthalene-1,8-diamine
• CAS: 1394231-60-7
• 化学式: C₂₁H₂₄N₂O
• 分子量: 320.434
• InChiKey: RJKYPQIMDCAVAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,8-bis(dimethylamino)-2-(4-methoxyphenyl)naphthalene 在 tetrafluoroboric acid 作用下， 以 乙醇 、 水 为溶剂， 以98%的产率得到1,8-bis(dimethylamino)-2-(4-methoxyphenyl)naphthalene hydrofluoroborate
  参考文献：
  名称：

  1,8-Bis(dimethylamino)-2-(4-methoxyphenyl)naphthalene: An electrospray-active analogue for η6-coordinating ligands

  摘要：

  1,8-Bis(dimethylamino)-2-(4-methoxyphenyl)naphthalene (1) was synthesized for use as an eta(6)-coordinating ligand with a chargeable tag for ESI-MS analysis. The pK(a) of the proton sponge moiety was essentially unaffected by addition of the anisole group (pK(a) = 18.2 +/- 0.7 at 297 K in CD3CN). Cr(eta(6)-1)(CO)(3) (2) was prepared to demonstrate the utility of (1) as an ESI tag and 2 was easily visible by ESI(+)-MS. A single crystal structure of the complex showed eta(6)-binding of the ligand as expected with the charged moiety being far removed from the metal centre. The gas-phase reactivity of 2 was found to match that of the analogous uncharged chromium carbonyl complex Cr(C6H5OCH3)(CO)(3) indicating that 1 has potential as a chargeable tag for the study of organometallic complexes and their reactions by ESI-MS. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.07.009
• 作为产物：
  描述：

  4-甲氧基苯硼酸 、 2-bromo-1,8-bis(dimethylamino)naphthalene 在 palladium diacetate 、 碳酸氢钠 、 三苯基膦 作用下， 以 丙醇 、 水 为溶剂， 反应 12.0h， 以41%的产率得到1,8-bis(dimethylamino)-2-(4-methoxyphenyl)naphthalene
  参考文献：
  名称：

  1,8-Bis(dimethylamino)-2-(4-methoxyphenyl)naphthalene: An electrospray-active analogue for η6-coordinating ligands

  摘要：

  1,8-Bis(dimethylamino)-2-(4-methoxyphenyl)naphthalene (1) was synthesized for use as an eta(6)-coordinating ligand with a chargeable tag for ESI-MS analysis. The pK(a) of the proton sponge moiety was essentially unaffected by addition of the anisole group (pK(a) = 18.2 +/- 0.7 at 297 K in CD3CN). Cr(eta(6)-1)(CO)(3) (2) was prepared to demonstrate the utility of (1) as an ESI tag and 2 was easily visible by ESI(+)-MS. A single crystal structure of the complex showed eta(6)-binding of the ligand as expected with the charged moiety being far removed from the metal centre. The gas-phase reactivity of 2 was found to match that of the analogous uncharged chromium carbonyl complex Cr(C6H5OCH3)(CO)(3) indicating that 1 has potential as a chargeable tag for the study of organometallic complexes and their reactions by ESI-MS. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.07.009