1-[(2,2,6,6-Tetramethyl-1-oxidopiperidin-4-yl)amino]-3-[(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)amino]propan-2-ol | 1640998-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-[(2,2,6,6-Tetramethyl-1-oxidopiperidin-4-yl)amino]-3-[(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)amino]propan-2-ol
• 英文别名: 1-[(2,2,6,6-tetramethyl-1-oxidopiperidin-4-yl)amino]-3-[(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)amino]propan-2-ol
• CAS: 1640998-18-0
• 化学式: C₂₁H₄₆N₄O₃
• 分子量: 402.621
• InChiKey: QIKQRSOFAKXTJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.7
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2,2,6,6-Tetramethyl-1-oxidopiperidin-4-yl)amino]-3-[(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)amino]propan-2-ol 在 lithium perchlorate 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 生成 C₃₅H₇₄N₅O₇
  参考文献：
  名称：

  Synthesis and evaluation of nitroxide-based oligoradicals for low-temperature dynamic nuclear polarization in solid state NMR

  摘要：

  We describe the synthesis of new nitroxide-based biradical, triradical, and tetraradical compounds and the evaluation of their performance as paramagnetic dopants in dynamic nuclear polarization (DNP) experiments in solid state nuclear magnetic resonance (NMR) spectroscopy with magic-angle spinning (MAS). Under our experimental conditions, which include temperatures in the 25-30 K range, a 9.4 T magnetic field, MAS frequencies of 6.2-6.8 kHz, and microwave irradiation at 264.0 GHz from a 800 mW extended interaction oscillator source, the most effective compounds are triradicals that are related to the previously-described compound DOTOPA-TEMPO (see Thurber et al., 2010), but have improved solubility in glycerol/water solvent near neutral pH. Using these compounds at 30 mM total nitroxide concentration, we observe DNP enhancement factors of 92-128 for cross-polarized C-13 NMR signals from N-15,C-13-labeled melittin in partially protonated glycerol/water, and build-up times of 2.6-3.8 s for H-1 spin polarizations. Net sensitivity enhancements with biradical and tetraradical dopants, taking into account absolute C-13 NMR signal amplitudes and build-up times, are approximately 2-4 times lower than with the best triradicals. Published by Elsevier Inc.

  DOI：

  10.1016/j.jmr.2014.05.002
• 作为产物：
  描述：

  1,3-二溴-2-丙醇 、 tempamine 在 sodium hydroxide 作用下， 以85%的产率得到1-[(2,2,6,6-Tetramethyl-1-oxidopiperidin-4-yl)amino]-3-[(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)amino]propan-2-ol
  参考文献：
  名称：

  Synthesis and evaluation of nitroxide-based oligoradicals for low-temperature dynamic nuclear polarization in solid state NMR

  摘要：

  We describe the synthesis of new nitroxide-based biradical, triradical, and tetraradical compounds and the evaluation of their performance as paramagnetic dopants in dynamic nuclear polarization (DNP) experiments in solid state nuclear magnetic resonance (NMR) spectroscopy with magic-angle spinning (MAS). Under our experimental conditions, which include temperatures in the 25-30 K range, a 9.4 T magnetic field, MAS frequencies of 6.2-6.8 kHz, and microwave irradiation at 264.0 GHz from a 800 mW extended interaction oscillator source, the most effective compounds are triradicals that are related to the previously-described compound DOTOPA-TEMPO (see Thurber et al., 2010), but have improved solubility in glycerol/water solvent near neutral pH. Using these compounds at 30 mM total nitroxide concentration, we observe DNP enhancement factors of 92-128 for cross-polarized C-13 NMR signals from N-15,C-13-labeled melittin in partially protonated glycerol/water, and build-up times of 2.6-3.8 s for H-1 spin polarizations. Net sensitivity enhancements with biradical and tetraradical dopants, taking into account absolute C-13 NMR signal amplitudes and build-up times, are approximately 2-4 times lower than with the best triradicals. Published by Elsevier Inc.

  DOI：

  10.1016/j.jmr.2014.05.002

文献信息

• Synthesis and evaluation of nitroxide-based oligoradicals for low-temperature dynamic nuclear polarization in solid state NMR
  作者：Wai-Ming Yau、Kent R. Thurber、Robert Tycko

  DOI：10.1016/j.jmr.2014.05.002

  日期：2014.7

  We describe the synthesis of new nitroxide-based biradical, triradical, and tetraradical compounds and the evaluation of their performance as paramagnetic dopants in dynamic nuclear polarization (DNP) experiments in solid state nuclear magnetic resonance (NMR) spectroscopy with magic-angle spinning (MAS). Under our experimental conditions, which include temperatures in the 25-30 K range, a 9.4 T magnetic field, MAS frequencies of 6.2-6.8 kHz, and microwave irradiation at 264.0 GHz from a 800 mW extended interaction oscillator source, the most effective compounds are triradicals that are related to the previously-described compound DOTOPA-TEMPO (see Thurber et al., 2010), but have improved solubility in glycerol/water solvent near neutral pH. Using these compounds at 30 mM total nitroxide concentration, we observe DNP enhancement factors of 92-128 for cross-polarized C-13 NMR signals from N-15,C-13-labeled melittin in partially protonated glycerol/water, and build-up times of 2.6-3.8 s for H-1 spin polarizations. Net sensitivity enhancements with biradical and tetraradical dopants, taking into account absolute C-13 NMR signal amplitudes and build-up times, are approximately 2-4 times lower than with the best triradicals. Published by Elsevier Inc.