2-[双[(1-甲基咪唑-2-基)甲基]氨基]乙酸 | 184647-13-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-[双[(1-甲基咪唑-2-基)甲基]氨基]乙酸
• 英文名称: N,N-bis(2-(1-methylimidazolyl)methyl)glycine
• 英文别名: (bis((1-methylimidazol-2-yl)methyl)amino)acetic acid；Glycine, N,N-bis[(1-methyl-1H-imidazol-2-yl)methyl]-；2-[bis[(1-methylimidazol-2-yl)methyl]amino]acetic acid
• CAS: 184647-13-0
• 化学式: C₁₂H₁₇N₅O₂
• 分子量: 263.299
• InChiKey: GFJYENTXZPVMBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  76.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  iron(III) chloride hexahydrate 、 2-[双[(1-甲基咪唑-2-基)甲基]氨基]乙酸 在 piperidine 作用下， 以 甲醇 为溶剂， 以60%的产率得到[Fe(III)((bis((1-methylimidazol-2-yl)methyl)amino)acetate)Cl2]
  参考文献：
  名称：

  A New Tripodal Tetradentate Ligand and Its Iron(III) Complex, as a Model for Mononuclear Non-Heme Iron Active Sites. Reactivity Studies toward Dioxygen and Superoxide

  摘要：

  The new biomimetic ligand (bis((1-methylimidazol-2-yl)methyl)amino) acetic acid (LH) has been synthesized, which increases the growing family of tripodal tetradentate ligands. Reaction of LH with FeCl3 . 6H(2)O allowed us to obtain the corresponding iron(III) complex [Fe(L)Cl-2]. The crystal structure reveals mononuclear neutral molecules with four chiral molecules per asymmetric unit (crystal data: monoclinic, P2(1), a = 12.564(5) Angstrom, b = 25.960(10) Angstrom, c = 9.875(4) Angstrom, alpha = 90.000, beta = 60.494(4)degrees, gamma = 90.00 degrees, V = 3221(2) Angstrom(3), Z = 8, R = 0.0601 for 2433 unique reflections with F-o > 4 sigma(F) and 452 variable parameters). The iron(III) center is located in a distorted octahedral environment consisting of four donor atoms from the ligand L, two imidazole nitrogens, an amine nitrogen, and one oxygen of the carboxylate group, with the 6-fold coordination being completed by two chloride anions. UV-vis and EPR spectra are solvent dependent due to the two labile chloride positions. Cyclic voltammograms run under an argon atmosphere exhibit a one-electron quasi-reversible redox process (E(o) = -0.015 V vs SCE in DMSO). The reaction of the complex with dioxygen and superoxide has been investigated through UV-vis spectroscopic and electrochemical studies. Direct UV-vis spectroscopic observations upon reaction with potassium superoxide, KO2, dissolved in DMSO indicate that a new species is formed, symbolyzed [Fe(III)-O-2(-)]. Comparison of the cyclic voltammograms obtained under argon or in the presence of dioxygen unambiguously indicates that the reduced form of the complex reacts with dioxygen. The buildup of a new species is confirmed by controlled potential electrolysis experiments of the associated voltammograms in the presence of dioxygen. This new species, symbolyzed [Fe(II)-O-2], has been shown to be stable even in the absence of dioxygen. Its UV-vis spectrum is superimposable with the spectrum of [Fe(III)-O-2(-)], indicating that the same oxygenated entity has been formed. Reaction of superoxide with the iron(III) complex has also been monitored through cyclic voltammetry, which confirms that superoxide is reactive toward the complex.

  DOI：

  10.1021/ic951060m

文献信息

• Structure regulation of Nickel (II) complexes with imidazole–tripodal ligand by altering the counter anions and the reaction conditions
  作者：Yan An、Xiao-Feng Li、Yu-Liang Zhang、Yan-Sheng Yin、Jing-Jia Sun、Shi-Fang Tong、Hong Yang、Shi-Ping Yang

  DOI：10.1016/j.inoche.2013.09.067

  日期：2013.12

  Abstract For the reaction products of N,N-bis(2-(1-methylimidazolyl)methyl)glycine (HL) with nickel (II), the conversion from a mononuclear complex of [NiL(H2O)2]NO3 · CH3OH (1) to a trinuclear complex of [NiL(H2O)2][Ni(H2O)4(CH3O)2]2(SO4)2 · (H2O)2 (2) was achieved by altering the types of the counter anions and the pH value of the reaction system. The coordination structures were studied by single-crystal

  摘要 对于 N,N-双(2-(1-甲基咪唑基)甲基)甘氨酸 (HL) 与镍 (II) 的反应产物，由 [NiL(H2O)2]NO3 · CH3OH (1 ) [NiL(H2O)2][Ni(H2O)4(CH3O)2]2(SO4)2 · (H2O)2 (2) 的三核复合物是通过改变抗衡阴离子的类型和 pH 值实现的反应体系的价值。通过单晶X射线分析研究配位结构。测量电化学和磁性能以揭示结构-性能关系。
• A New Tripodal Tetradentate Ligand and Its Iron(III) Complex, as a Model for Mononuclear Non-Heme Iron Active Sites. Reactivity Studies toward Dioxygen and Superoxide
  作者：Marie-Carmen Rodriguez、Irène Morgenstern-Badarau、Michèle Cesario、Jean Guilhem、Bineta Keita、Louis Nadjo

  DOI：10.1021/ic951060m

  日期：1996.1.1

  The new biomimetic ligand (bis((1-methylimidazol-2-yl)methyl)amino) acetic acid (LH) has been synthesized, which increases the growing family of tripodal tetradentate ligands. Reaction of LH with FeCl3 . 6H(2)O allowed us to obtain the corresponding iron(III) complex [Fe(L)Cl-2]. The crystal structure reveals mononuclear neutral molecules with four chiral molecules per asymmetric unit (crystal data: monoclinic, P2(1), a = 12.564(5) Angstrom, b = 25.960(10) Angstrom, c = 9.875(4) Angstrom, alpha = 90.000, beta = 60.494(4)degrees, gamma = 90.00 degrees, V = 3221(2) Angstrom(3), Z = 8, R = 0.0601 for 2433 unique reflections with F-o > 4 sigma(F) and 452 variable parameters). The iron(III) center is located in a distorted octahedral environment consisting of four donor atoms from the ligand L, two imidazole nitrogens, an amine nitrogen, and one oxygen of the carboxylate group, with the 6-fold coordination being completed by two chloride anions. UV-vis and EPR spectra are solvent dependent due to the two labile chloride positions. Cyclic voltammograms run under an argon atmosphere exhibit a one-electron quasi-reversible redox process (E(o) = -0.015 V vs SCE in DMSO). The reaction of the complex with dioxygen and superoxide has been investigated through UV-vis spectroscopic and electrochemical studies. Direct UV-vis spectroscopic observations upon reaction with potassium superoxide, KO2, dissolved in DMSO indicate that a new species is formed, symbolyzed [Fe(III)-O-2(-)]. Comparison of the cyclic voltammograms obtained under argon or in the presence of dioxygen unambiguously indicates that the reduced form of the complex reacts with dioxygen. The buildup of a new species is confirmed by controlled potential electrolysis experiments of the associated voltammograms in the presence of dioxygen. This new species, symbolyzed [Fe(II)-O-2], has been shown to be stable even in the absence of dioxygen. Its UV-vis spectrum is superimposable with the spectrum of [Fe(III)-O-2(-)], indicating that the same oxygenated entity has been formed. Reaction of superoxide with the iron(III) complex has also been monitored through cyclic voltammetry, which confirms that superoxide is reactive toward the complex.