2,6-bis(aminomethyl)-4-methylphenol | 173178-17-1

• 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(aminomethyl)-4-methylphenol
• 英文别名: 2,6-bis{[N-(2-dimethylaminoethyl)-N-methyl]-aminomethyl}-4-methylphenol；2,6-bis(N-(2-dimethylaminoethyl)-N-methyl)-4-methylphenol；2,6-bis{N-(2-dimethylaminoethyl)-N-methyl}-4-methylphenol；2,6-Bis({[2-(dimethylamino)ethyl](methyl)amino}methyl)-4-methylphenol；2,6-bis[[2-(dimethylamino)ethyl-methylamino]methyl]-4-methylphenol
• CAS: 173178-17-1
• 化学式: C₁₉H₃₆N₄O
• 分子量: 336.521
• InChiKey: HWCBKWMBMXDRSN-UHFFFAOYSA-N

物化性质

• 沸点：
  401.2±40.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  33.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  zinc(II) acetate dihydrate 、 2,6-bis(aminomethyl)-4-methylphenol 在 sodium hydride 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以86%的产率得到[(CH3C6H2(CH2N(CH3)CH2CH2N(CH3)2)2O)Zn2(μ-acetato)2](acetate)
  参考文献：
  名称：

  使用五齿酚盐配体的双核锌络合物。

  摘要：

  报告了15种双核锌配合物的合成和表征，包括5种配合物的X射线晶体结构。合成了利用对甲酚作为两个锌中心和一组三个相关配体之间的桥连单元的配体基序。2,6-bis（R）-对甲酚（其中R为CH（2）NMe（CH（2））（2）NMe（2）= L（1），CH = N（CH（2））（ 2）NMe（2）= L（2），CH（2）NH（CH（2））（2）NMe（2）= L（3））。已经制备了三卤化二锌配合物[L（n）Zn（2）（mu-X）X（2）]（其中X = Cl，Br，I）。将三卤化物配合物用乙醇钾处理，导致桥联卤化物基团的定量取代得到[L（n）Zn（2）（mu-OEt）X（2）]。乙醇二锌络合物作为丙交酯开环聚合反应的引发剂进行了现场测试。三乙酸二锌配合物也已经合成[L（n）Zn（2）（OAc）（3）]，以及包含两个桥接乙酸盐基团[L（n）Zn（2）（mu-OAc）（2）] [BPh（4）]的阳离子二

  DOI：

  10.1021/ic8014173
• 作为产物：
  描述：

  对甲酚 、 N,N,N'-三甲基乙二胺 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醇 为溶剂， 反应 8.5h， 生成 2,6-bis(aminomethyl)-4-methylphenol
  参考文献：
  名称：

  Hydrolysis of β-Lactam Antibiotics Catalyzed by Dinuclear Zinc(II) Complexes:  Functional Mimics of Metallo-β-lactamases

  摘要：

  Three stable dinuclear zinc(II) complexes, [Zn2L1(mu-NO3)(NO3)(2)] and [Zn2L1(mu-OMe)(NO3)(2)], where L-1 is 2,6-bis {{N-(2-dimethylaminoethyl)-N-methyl]aminomethyl}-4-methylphenolate, and [Zn2L2(NO3)(3)], where L-2 is 2-{[N-(2-dimethylaminoethyl)-N-methyl]aminomethyl}-4-bromo-6-{[N'-2-(2'-pyridyl)ethyl]aminomethyl}phenolate, were synthesized and characterized in the solid stare and in aqueous solution. These complexes catalyze the hydrolysis of penicillin G and nitrocefin, serving as functional synthetic analogues of the metallo-beta-lactamases, bacterial enzymes responsible for antibiotic resistance. The mechanism of the hydrolysis was studied in detail for the catalyst precursor [Zn2L1(mu-NO3)(NO3)(2)], which converts into [Zn2L1(mu-OH)(NO3), (sol)(2-n)]((2-n)+) in the presence of water. The complex [Zn2L1(mu-OH)(No-3)(2)] (n = 2) was characterized in the solid state. Initial coordination of the substrate carboxylate group is followed by the rate-limiting nucleophilic attack of the bridging hydroxide at the beta-lactam carbonyl group in aqueous solution. The product is formed upon fast protonation of the intermediate. Mononuclear complexes Zn(cyclen)(NO3)(2) and Zn(bpta)(NO3)(2) are as reactive in the beta-lactam hydrolysis as the dinuclear complexes. Consequently, the second zinc ion is not required for catalytic activity.

  DOI：

  10.1021/ja993704l

文献信息

• Comparison of structurally analogous Zn₂, Co₂, and Mg₂catalysts for the polymerization of cyclic esters
  作者：Laurie E. Breyfogle、Charlotte K. Williams、Victor G. Young, Jr.、Marc A. Hillmyer、William B. Tolman

  DOI：10.1039/b507014g

  日期：——

  Three dimetallic monoethoxide complexes supported by a binucleating phenoxide ligand, LM2Cl2OEt (M = Zn, Co, or Mg), were prepared and shown by X-ray crystallography to be structurally analogous. Comparative studies of their cyclic ester polymerization reactivity revealed different trends for reactions with ε-caprolactone and lactide, however, implicating complicated effects of metal ion variation in these polymerizations.

  通过双核化苯氧基配体支撑的三金属单乙氧基配合物 LM2Cl2OEt（M = Zn、Co 或 Mg）被制备出来，并通过 X 射线晶体学证明它们在结构上相似。它们对环酯聚合反应性的比较研究表明，在与ε-己内酯和乳酸酯的反应中呈现出不同的趋势，然而，这暗示了在这些聚合中金属离子变化所带来的复杂影响。
• Metalloenzyme inspired dizinc catalyst for the polymerization of lactide
  作者：Charlotte K. Williams、Neil R. Brooks、Marc A. Hillmyer、William B. Tolman

  DOI：10.1039/b206437e

  日期：2002.9.11

  A new dizinc–monoalkoxide complex supported by a dinucleating ligand was structurally characterized and shown to be a highly active catalyst for the controlled polymerization of lactide.

  一种由双核配体负载的新型二锌-单醇盐络合物进行了结构表征，并表明它是丙交酯受控聚合的高活性催化剂。
• Hydrolysis of β-Lactam Antibiotics Catalyzed by Dinuclear Zinc(II) Complexes:  Functional Mimics of Metallo-β-lactamases
  作者：Natalia V. Kaminskaia、Bernhard Spingler、Stephen J. Lippard

  DOI：10.1021/ja993704l

  日期：2000.7.1

  Three stable dinuclear zinc(II) complexes, [Zn2L1(mu-NO3)(NO3)(2)] and [Zn2L1(mu-OMe)(NO3)(2)], where L-1 is 2,6-bis N-(2-dimethylaminoethyl)-N-methyl]aminomethyl}-4-methylphenolate, and [Zn2L2(NO3)(3)], where L-2 is 2-[N-(2-dimethylaminoethyl)-N-methyl]aminomethyl}-4-bromo-6-[N'-2-(2'-pyridyl)ethyl]aminomethyl}phenolate, were synthesized and characterized in the solid stare and in aqueous solution. These complexes catalyze the hydrolysis of penicillin G and nitrocefin, serving as functional synthetic analogues of the metallo-beta-lactamases, bacterial enzymes responsible for antibiotic resistance. The mechanism of the hydrolysis was studied in detail for the catalyst precursor [Zn2L1(mu-NO3)(NO3)(2)], which converts into [Zn2L1(mu-OH)(NO3), (sol)(2-n)]((2-n)+) in the presence of water. The complex [Zn2L1(mu-OH)(No-3)(2)] (n = 2) was characterized in the solid state. Initial coordination of the substrate carboxylate group is followed by the rate-limiting nucleophilic attack of the bridging hydroxide at the beta-lactam carbonyl group in aqueous solution. The product is formed upon fast protonation of the intermediate. Mononuclear complexes Zn(cyclen)(NO3)(2) and Zn(bpta)(NO3)(2) are as reactive in the beta-lactam hydrolysis as the dinuclear complexes. Consequently, the second zinc ion is not required for catalytic activity.
• Dinuclear Zinc Complexes Using Pentadentate Phenolate Ligands
  作者：Paul D. Knight、Andrew J. P. White、Charlotte K. Williams

  DOI：10.1021/ic8014173

  日期：2008.12.15

  The synthesis and characterization of 15 dinuclear zinc complexes are reported, including the X-ray crystal structures of 5 complexes. The ligand motif utilizing p-cresol as a bridging unit between the two zinc centers and a set of three related ligands has been synthesized; 2,6-bis(R)-p-cresol (where R is CH(2)NMe(CH(2))(2)NMe(2) = L(1), CH=N(CH(2))(2)NMe(2) = L(2), and CH(2)NH(CH(2))(2)NMe(2) = L(3))

  报告了15种双核锌配合物的合成和表征，包括5种配合物的X射线晶体结构。合成了利用对甲酚作为两个锌中心和一组三个相关配体之间的桥连单元的配体基序。2,6-bis（R）-对甲酚（其中R为CH（2）NMe（CH（2））（2）NMe（2）= L（1），CH = N（CH（2））（ 2）NMe（2）= L（2），CH（2）NH（CH（2））（2）NMe（2）= L（3））。已经制备了三卤化二锌配合物[L（n）Zn（2）（mu-X）X（2）]（其中X = Cl，Br，I）。将三卤化物配合物用乙醇钾处理，导致桥联卤化物基团的定量取代得到[L（n）Zn（2）（mu-OEt）X（2）]。乙醇二锌络合物作为丙交酯开环聚合反应的引发剂进行了现场测试。三乙酸二锌配合物也已经合成[L（n）Zn（2）（OAc）（3）]，以及包含两个桥接乙酸盐基团[L（n）Zn（2）（mu-OAc）（2）] [BPh（4）]的阳离子二