2,6-bis((diethylamino)methyl)-4-t-butyl-phenol | 28938-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-bis((diethylamino)methyl)-4-t-butyl-phenol
• 英文别名: 4-Tert-butyl-2,6-bis(diethylaminomethyl)phenol
• CAS: 28938-84-3
• 化学式: C₂₀H₃₆N₂O
• 分子量: 320.519
• InChiKey: AXCTUTWXRVYNFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  chloroauric acid 、 2,6-bis((diethylamino)methyl)-4-t-butyl-phenol 以 二氯甲烷 、 乙腈 为溶剂， 生成 monoaureate of 2,6-bis((diethylamino)methyl)-4-t-butyl-phenol
  参考文献：
  名称：

  质子NMR研究2,6-双（（二乙基氨基）甲基）-4-R-苯酚单酸氢键体系中集体质子运动

  摘要：

  Eleven mono- and diaurates of 2,6-bis((diethylamino)methyl)-4-R-phenols were studied in CD2Cl2 solutions using H-1 NMR spectroscopy. With the monoaurates a collective proton fluctuation occurs in the intramolecular hydrogen-bonded system as known from IR results. With increasing acidity of the phenolic group a low field shift of the sipal of the hydrogen-bonded protons is found, indicating increasing deshielding. The protons arc most strongly deshielded in the R = Cl system, from which it is known that it shows the largest proton polarizability. With further increasing acidity the protons are more and more shielded by the N atoms. When the proton limiting structure in which the hydrogen-bonded protons are preferentially present at the N atoms becomes realized, the signals of the Ph-CH2 and the N-CH2 protons are strongly broadened. When the protons are almost localized at these N atoms, a doublet and an octet, respectively. are observed. These effects arise due to spin-spin coupling between the methylene protons and the NH+ protons.

  DOI：

  10.1021/j100195a012
• 作为产物：
  描述：

  聚合甲醛 、 4-叔丁基苯酚 、 二乙胺 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 30.0h， 以98%的产率得到2,6-bis((diethylamino)methyl)-4-t-butyl-phenol
  参考文献：
  名称：

  2-和2,6-双-(N,N-二乙基氨基甲基)-4R-苯酚中氢键的制备和核磁共振表征

  摘要：

  摘要 在氯仿-d1 溶液中制备了一系列衍生自4-取代酚的曼尼希单碱和双碱，并通过1H 和13C NMR 光谱进行了研究。曼尼希碱中分子内氢键结合的质子的化学位移取决于母体酚的 pKa。已发现哈米特常数、σp 和对位碳原子的 13C NMR 化学位移之间存在相关性。从 1H 和 13C NMR 光谱获得的所有结果表明，在二碱的情况下，OH 质子对称地桥接两个氮原子。早期的红外研究表明，质子在每个二氮氧化物分子中的两个氧原子之间振荡。然而，平均而言，该结构是对称的。

  DOI：

  10.1016/0022-2860(91)80014-u

文献信息

• US3935160A
  申请人：——

  公开号：US3935160A

  公开（公告）日：1976-01-27
• Preparation and NMR characterisation of hydrogen bonding in 2- and 2,6-bis- (N,N-diethylaminomethyl) - 4R-phenols
  作者：Bogumil Brycki、Hanna Maciejewska、Bogumil Brzezinski、Georg Zundel

  DOI：10.1016/0022-2860(91)80014-u

  日期：1991.6

  phenols were prepared and investigated by 1H and 13C NMR spectroscopy in chloroform-d1 solution. The chemical shifts of intramolecular hydrogen-bonded protons in Mannich bases depend on the pKa of the parent phenols. A correlation between Hammett's constants, σp, and 13C NMR chemical shifts of para carbon atoms has been found. All the results obtained from 1H and 13C NMR spectra show that in the case

  摘要 在氯仿-d1 溶液中制备了一系列衍生自4-取代酚的曼尼希单碱和双碱，并通过1H 和13C NMR 光谱进行了研究。曼尼希碱中分子内氢键结合的质子的化学位移取决于母体酚的 pKa。已发现哈米特常数、σp 和对位碳原子的 13C NMR 化学位移之间存在相关性。从 1H 和 13C NMR 光谱获得的所有结果表明，在二碱的情况下，OH 质子对称地桥接两个氮原子。早期的红外研究表明，质子在每个二氮氧化物分子中的两个氧原子之间振荡。然而，平均而言，该结构是对称的。
• Proton NMR investigation of the collective proton motion in hydrogen-bonded systems of monoaurates of 2,6-bis((diethylamino)methyl)-4-R-phenols
  作者：Bogumil Brzezinski、Hanna Maciejewska、Georg Zundel

  DOI：10.1021/j100195a012

  日期：1992.8

  Eleven mono- and diaurates of 2,6-bis((diethylamino)methyl)-4-R-phenols were studied in CD2Cl2 solutions using H-1 NMR spectroscopy. With the monoaurates a collective proton fluctuation occurs in the intramolecular hydrogen-bonded system as known from IR results. With increasing acidity of the phenolic group a low field shift of the sipal of the hydrogen-bonded protons is found, indicating increasing deshielding. The protons arc most strongly deshielded in the R = Cl system, from which it is known that it shows the largest proton polarizability. With further increasing acidity the protons are more and more shielded by the N atoms. When the proton limiting structure in which the hydrogen-bonded protons are preferentially present at the N atoms becomes realized, the signals of the Ph-CH2 and the N-CH2 protons are strongly broadened. When the protons are almost localized at these N atoms, a doublet and an octet, respectively. are observed. These effects arise due to spin-spin coupling between the methylene protons and the NH+ protons.