bis(5-tert-butyl-3-methylpyrazol-2-yl)acetic acid | 561001-25-0

• 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
• 英文名称: bis(5-tert-butyl-3-methylpyrazol-2-yl)acetic acid
• 英文别名: 2,2-Bis(3-tert-butyl-5-methylpyrazol-1-yl)acetic acid；2,2-bis(3-tert-butyl-5-methylpyrazol-1-yl)acetic acid
• CAS: 561001-25-0
• 化学式: C₁₈H₂₈N₄O₂
• 分子量: 332.446
• InChiKey: BPOOBZQPPGLYTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(5-tert-butyl-3-methylpyrazol-2-yl)acetic acid 、 zinc(II) chloride 在 NaOCH₃ 作用下， 以 乙腈 为溶剂， 以39%的产率得到[bis(5-tert-butyl-3-methylpyrazol-2-yl)acetato](chloro)zinc(II)
  参考文献：
  名称：

  Synthesis and characterization of several zinc(II) complexes containing the bulky heteroscorpionate ligand bis(5-tert-butyl-3-methylpyrazol-2-yl)acetate: relevance to the resting states of the zinc(II) enzymes thermolysin and carboxypeptidase A

  摘要：

  The syntheses and characterization of a series of zinc complexes containing the tripodal ligand bis(5-tert-butyl-3-methylpyrazol-2yl)acetic acid (H2) which is designed to model the 2-His-1-carboxylate facial triad observed in the active sites of various metalloenzymes such as carboxypeptidase A (CPA) and thermolysin (TLN) are reported. Pseudotetrahedral complexes isolated include [Zn2(CH3)], [Zn2(Cl)], [Zn2(SPh)], [Zn2(OAc)], [Zn2(NCS)] and [Zn2(AH)]. In addition, a four (solution) or five-coordinate (solid state) cationic zinc aqua complex, [Zn2(OH2)](+) and a 5-coordinate zinc acetohydroxamate complex, [Zn2(AH)] were synthesized and structurally characterized. The former represents a structural mimic of the resting state while the latter depicts the inhibited state of zinc enzymes CPA and TLN. Crystal data: [Zn2(CH3)] crystallizes in the triclinic space group P1, with cell dimensions a = 6.638(6) Angstrom, b = 12.249(10) Angstrom, c = 13.327(12) Angstrom, alpha = 82.862(15)degrees, beta = 76.811(15)degrees, gamma = 88.988(17)degrees and Z = 2; [Zn2(Cl)] crystallizes in the triclinic space group P1, with cell dimensions a = 8.9933(7) Angstrom, b = 9.7985(8) Angstrom, c = 12.1536(9) Angstrom, alpha = 94.0420(10)degrees, beta = 105.3950(10)degrees, gamma = 95.6490(10)degrees and Z = 2; [Zn2(SPh)].0.5CH(2)Cl(2) crystallizes in the triclinic space group P1, with cell dimensions a = 12.1273(15) Angstrom, b = 12.9073(16) Angstrom, c = 17.824(2) Angstrom, alpha = 87.194(2)degrees, beta = 78.769(3)degrees, gamma = 76.027(2)degrees and Z = 4; [Zn2(OH2)]ClO4 crystallizes in the monoclinic space group P2(1)/n, with cell dimensions a = 12.620(2) Angstrom, b = 11.1416(18) Angstrom, c = 19.315(3) Angstrom, beta = 101.883(2)degrees, and Z = 4; [Zn2(AH)] . 3.25CH(2)Cl(2) crystallizes in the orthorhombic space group Pccn, with cell dimensions a = 23.7791(6) Angstrom, b = 14.1675(3) Angstrom, c = 22.1213(5) Angstrom, alpha = beta = gamma = 90degrees and Z = 8. The H-1 NMR spectra of these diamagnetic zinc complexes suggests that all complexes retain their overall symmetry in solution. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0020-1693(02)01338-5

文献信息

• Synthesis and characterization of several zinc(II) complexes containing the bulky heteroscorpionate ligand bis(5-tert-butyl-3-methylpyrazol-2-yl)acetate: relevance to the resting states of the zinc(II) enzymes thermolysin and carboxypeptidase A
  作者：Brian S Hammes、Matthew T Kieber-Emmons、Joseph A Letizia、Zahida Shirin、Carl J Carrano、Lev N Zakharov、Arnold L Rheingold

  DOI：10.1016/s0020-1693(02)01338-5

  日期：2003.3

  The syntheses and characterization of a series of zinc complexes containing the tripodal ligand bis(5-tert-butyl-3-methylpyrazol-2yl)acetic acid (H2) which is designed to model the 2-His-1-carboxylate facial triad observed in the active sites of various metalloenzymes such as carboxypeptidase A (CPA) and thermolysin (TLN) are reported. Pseudotetrahedral complexes isolated include [Zn2(CH3)], [Zn2(Cl)], [Zn2(SPh)], [Zn2(OAc)], [Zn2(NCS)] and [Zn2(AH)]. In addition, a four (solution) or five-coordinate (solid state) cationic zinc aqua complex, [Zn2(OH2)](+) and a 5-coordinate zinc acetohydroxamate complex, [Zn2(AH)] were synthesized and structurally characterized. The former represents a structural mimic of the resting state while the latter depicts the inhibited state of zinc enzymes CPA and TLN. Crystal data: [Zn2(CH3)] crystallizes in the triclinic space group P1, with cell dimensions a = 6.638(6) Angstrom, b = 12.249(10) Angstrom, c = 13.327(12) Angstrom, alpha = 82.862(15)degrees, beta = 76.811(15)degrees, gamma = 88.988(17)degrees and Z = 2; [Zn2(Cl)] crystallizes in the triclinic space group P1, with cell dimensions a = 8.9933(7) Angstrom, b = 9.7985(8) Angstrom, c = 12.1536(9) Angstrom, alpha = 94.0420(10)degrees, beta = 105.3950(10)degrees, gamma = 95.6490(10)degrees and Z = 2; [Zn2(SPh)].0.5CH(2)Cl(2) crystallizes in the triclinic space group P1, with cell dimensions a = 12.1273(15) Angstrom, b = 12.9073(16) Angstrom, c = 17.824(2) Angstrom, alpha = 87.194(2)degrees, beta = 78.769(3)degrees, gamma = 76.027(2)degrees and Z = 4; [Zn2(OH2)]ClO4 crystallizes in the monoclinic space group P2(1)/n, with cell dimensions a = 12.620(2) Angstrom, b = 11.1416(18) Angstrom, c = 19.315(3) Angstrom, beta = 101.883(2)degrees, and Z = 4; [Zn2(AH)] . 3.25CH(2)Cl(2) crystallizes in the orthorhombic space group Pccn, with cell dimensions a = 23.7791(6) Angstrom, b = 14.1675(3) Angstrom, c = 22.1213(5) Angstrom, alpha = beta = gamma = 90degrees and Z = 8. The H-1 NMR spectra of these diamagnetic zinc complexes suggests that all complexes retain their overall symmetry in solution. (C) 2002 Elsevier Science B.V. All rights reserved.