1,1-bis-(N-methylimidazol-2-yl)-1-hydroxyethane | 124226-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,1-bis-(N-methylimidazol-2-yl)-1-hydroxyethane
• 英文别名: 1,1-bis(N-methylimidazol-2-yl)-1-hydroxyethane；1,1-bis(N-methylimidazol-2-yl)ethanol；I+/-,1-Dimethyl-I+/--(1-methyl-1H-imidazol-2-yl)-1H-imidazole-2-methanol；1,1-bis(1-methylimidazol-2-yl)ethanol
• CAS: 124226-01-3
• 化学式: C₁₀H₁₄N₄O
• 分子量: 206.247
• InChiKey: SKOUCJIEPRPEEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  439.8±40.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-bis-(N-methylimidazol-2-yl)-1-hydroxyethane 在 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 作用下， 以 二氯甲烷 为溶剂， 以62 %的产率得到2,2’-(ethene-1,1-diyl)bis(1-methyl-1H-imidazole)
  参考文献：
  名称：

  用于金属蛋白组装的基于双（咪唑）的半胱氨酸标记工具

  摘要：

  通过设计实现精确的金属-蛋白质协调仍然是一个巨大的挑战。多齿、高金属亲和力的蛋白质修饰，无论是化学修饰还是重组修饰，都可以实现金属定位。然而，这些构建体通常体积庞大，构象和立体化学不明确，或协调饱和。在这里，我们通过与双（1-甲基咪唑-2-基）乙烯（“BMIE”）的半胱氨酸不可逆连接来扩展生物分子金属配位工具箱，从而生成紧凑的基于咪唑的金属配位配体。小分子硫醇（硫甲酚和 N-Boc-Cys）与 BMIE 的共轭添加证实了一般硫醇反应性。BMIE 加合物可与二齿金属离子 Cu ++和 Zn ++络合成二齿 (N 2 ) 和三齿 (N2 S*) 协调几何形状。使用 ESI-MS 测量模型蛋白（羧肽酶 G2 (CPG2) 的 S203C 变体）的半胱氨酸靶向 BMIE 修饰（pH 8.0 时产率 >90%），证实了其作为位点选择性生物缀合方法的实用性。ICP-MS 分析证实了 BMIE 修饰的 CPG2

  DOI：

  10.1016/j.jinorgbio.2023.112206
• 作为产物：
  描述：

  N-甲基咪唑 、 乙酸乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以60 %的产率得到1,1-bis-(N-methylimidazol-2-yl)-1-hydroxyethane
  参考文献：
  名称：

  用于金属蛋白组装的基于双（咪唑）的半胱氨酸标记工具

  摘要：

  通过设计实现精确的金属-蛋白质协调仍然是一个巨大的挑战。多齿、高金属亲和力的蛋白质修饰，无论是化学修饰还是重组修饰，都可以实现金属定位。然而，这些构建体通常体积庞大，构象和立体化学不明确，或协调饱和。在这里，我们通过与双（1-甲基咪唑-2-基）乙烯（“BMIE”）的半胱氨酸不可逆连接来扩展生物分子金属配位工具箱，从而生成紧凑的基于咪唑的金属配位配体。小分子硫醇（硫甲酚和 N-Boc-Cys）与 BMIE 的共轭添加证实了一般硫醇反应性。BMIE 加合物可与二齿金属离子 Cu ++和 Zn ++络合成二齿 (N 2 ) 和三齿 (N2 S*) 协调几何形状。使用 ESI-MS 测量模型蛋白（羧肽酶 G2 (CPG2) 的 S203C 变体）的半胱氨酸靶向 BMIE 修饰（pH 8.0 时产率 >90%），证实了其作为位点选择性生物缀合方法的实用性。ICP-MS 分析证实了 BMIE 修饰的 CPG2

  DOI：

  10.1016/j.jinorgbio.2023.112206

文献信息

• Nitridoosmium(VI) and nitridoruthenium(VI) complexes of cysteine(2-) and related ligands
  作者：Joseph J. Schwab、Elizabeth C. Wilkinson、Scott R. Wilson、Patricia A. Shapley

  DOI：10.1021/ja00016a031

  日期：1991.7

  Anionic complexes of nitridoruthenium(VI) and nitridoosmium(VI) containing covalently bound N-acetyl-L-cysteinato, 3-sulfidopropionato, and 3-sulfidopropionamidato ligands have been synthesized to model the binding of delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine to the iron center in the metalloenzyme isopenicillin N synthetase. The complexes are prepared by the reaction of N-acetyl-L-cysteine, 3-mercaptopropionic acid, and 3-mercaptopropionamide with [NBu(n)4][Os(N)(OSiMe3)4], [NBu(n)4][Os(N)Cl4], [NBu(n)4][Ru(N)(CH2SiMe3)4], or [NBu(n)4][Ru(N)(OSiMe3)4]. They have been characterized by elemental analysis and IR and NMR spectroscopy. Spectroscopic data show that the N-acetyl-L-cysteinato and 3-sulfidopropionato ligands are bound to the metal center through sulfur and oxygen, while the 3-sulfidopropionamidato ligands are bound through sulfur and nitrogen. The molecular structures of cis-[NBu(n)4][Os(N)(O2CCH2CH2S)2], [NBu(n)4][Os(N)O2CCH(NHCOCH3)CH2S}2], and [PPh4][Ru(N)(NHCOCH2CH2S)2)] were determined by single-crystal X-ray diffraction. These complexes were found to have distorted square-pyramidal geometry around the metal center. cis-[NBu(n)4][Os(N)(O2CCH2CH2S)2] crystallizes in monoclinic space group P2(1)/c with a = 13.718 (6) angstrom, b = 10.080 (3) angstrom, c = 19.890 (5) angstrom, beta = 92.16 (3) angstrom, and Z = 4. [NBu(n)4][Os(N)L-O2CCH(NHCOCH3)CH2S}2] crystallizes in monoclinic space group C2 with a = 18.371 (6) angstrom, b = 9.261 (1) angstrom, c = 21.125 (7) angstrom, beta = 102.92 (3) angstrom, and Z = 4. [PPh4][Ru(N)(NHCOCH2CH2S)2)] crystallizes in orthorhombic space group Pbca with a = 23.022 (1) angstrom, b = 16.120 (1) angstrom, c = 15.728 (1) angstrom, and Z = 8.
• Harding, Margaret M.; Sargeant, Benjamin; Bilyk, Alexander, Australian Journal of Chemistry, 1994, vol. 47, # 6, p. 1133 - 1142
  作者：Harding, Margaret M.、Sargeant, Benjamin、Bilyk, Alexander、Augoloupis, Steven

  DOI：——

  日期：——
• Boyd, Sue E.; Harding, Margaret M.; Buys, Irmi E., Australian Journal of Chemistry, 1993, vol. 46, # 8, p. 1307 - 1312
  作者：Boyd, Sue E.、Harding, Margaret M.、Buys, Irmi E.、Hambley, Trevor W.

  DOI：——

  日期：——
• Spin frustration: a hexanuclear ferric complex with a S = 5 ground state
  作者：James K. McCusker、Cheryl A. Christmas、Paula M. Hagen、Raj K. Chadha、Daniel F. Harvey、David N. Hendrickson

  DOI：10.1021/ja00016a030

  日期：1991.7

  The preparation and characterization of a hexanuclear Fe(III) complex possessing an unusual S = 5 ground state are described. Reaction of 1,1-bis(N-methylimidazol-2-yl)-1-hydroxyethane (1) with [Fe3O(OAc)6L3]X (2), where L = pyridine or H2O and X = ClO4- or NO3-, in CH3CN followed by recrystallization in CH2Cl2 affords crystals of [Fe6O2(OH)2(OAc)10(C10H13N4O)2].xCH2Cl2 (3.xCH2Cl2). Complex 3.8CH2Cl2 crystallizes in the triclinic space group P1BAR with a = 12.167 (2) angstrom, b = 12.921 (4) angstrom, c = 15.394 (4) angstrom, alpha = 114.41 (2)degrees, beta = 97.641 (15)degrees, gamma = 102.17 (2)degrees, V = 2087.4 (8) angstrom3, and Z = 1 at -100-degrees-C. The structure was refined with 4179 observed reflections (F > 6.0-sigma) to give R = 0.0465 and R(w) = 0.0591. The molecule resides at a center of inversion, making only three of the iron ions unique. Two of the iron ions have O6 coordination spheres, while the third has an O5N environment due to binding by one of the imidazole nitrogen atoms; the second imidazole ring of complex 1 remains uncoordinated. Complex 3 consists of two-mu-3-oxo Fe(III)3 triangular complexes bridged together at two vertices by two-mu-2-OH and four-mu-O2CCH3 ions. Fe-57 Mossbauer data can be fit to two quadrupole-split doublets in a 2:1 area ratio with delta = 0.383 (3) and 0.406 (6) mm/s and DELTA-E(Q) = 0.729 (5) and 1.056 (11) mm/s, respectively, at 300 K. The parameters are consistent with high-spin Fe(III). Magnetic susceptibility data at 10.00 kG in the temperature range 6-350 K reveal an increase in effective moment with decreasing temperature from 9.21-mu-B at 346.1 K to a maximum of 10.90-mu-B at 20.00 K. Variable-field magnetization data measured to 1.57 K at 40.00 kG saturate at a reduced magnetization M/N-mu-B of 9.2. Fitting of the magnetization data by full-matrix diagonalization and including axial zero-field interactions establish the ground state as having S = 5 with g = 1.94 and D = 0.22 cm-1. The origin of this ground state is described in terms of spin frustration within the hexanuclear core, and the results are compared to those found for a similar hexanuclear complex for which a S = 0 ground state was found.
• Harvey, Daniel F.; Christmas, Cheryl A.; McCusker, James K., Angewandte Chemie, 1991, vol. 103, p. 592 - 594
  作者：Harvey, Daniel F.、Christmas, Cheryl A.、McCusker, James K.、Hagen, Paula M.、Chadha, Raj K.、Hendrickson, David N.

  DOI：——

  日期：——