1,16-bis-(1H-imidazol-1-yl)hexadecane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,16-bis-(1H-imidazol-1-yl)hexadecane
• 英文别名: 1,16-bis(imidazole)hexadecane；1-(16-Imidazol-1-ylhexadecyl)imidazole
• 化学式: C₂₂H₃₈N₄
• 分子量: 358.571
• InChiKey: JXRJATDQMHMKBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,16-bis-(1H-imidazol-1-yl)hexadecane 在 copper(I) oxide 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  使用量子化学计算支持的单分子力谱激活铜双卡宾机械催化剂

  摘要：

  单分子力谱可以研究机械力对单个键的影响。通过确定充分激活键以引发解离所需的力，可以预测机械载体的行为。测量了激活用于自修复材料的铜双卡宾机械催化剂所需的力。通过使用绕过机械载体的安全线，可以精确定位所研究的键的解离，并确定室温下二甲亚砜中的断裂力范围为 1.6 至 2.6 nN。由于安全线的拉伸，Cu−C 键断裂时的平均长度增加与量子化学计算一致，但这些值表现出不寻常的散射。这种散射归因于机械载体的构象灵活性，其中包括螺纹结构的形成和安全线的反冲。

  DOI：

  10.1002/chem.202100555
• 作为产物：
  描述：

  氧杂环十七烷-2-酮 在 lithium aluminium tetrahydride 、 磷酸 、 phosphorus pentoxide 、 potassium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 10.5h， 生成 1,16-bis-(1H-imidazol-1-yl)hexadecane
  参考文献：
  名称：

  The anti-malarial activity of bivalent imidazolium salts

  摘要：

  A series of compounds containing bivalent imidazolium rings and one triazolium analog were synthesized and evaluated for their ability to inhibit the replication of Plasmodium falciparum cultures. The activity and selectivity of the compounds for P. falciparum cultures were found to depend on the presence of electron-deficient rings that were spaced an appropriate distance apart. The activity of the compounds was not critically dependent on the nature of the linker between the electron-deficient rings, an observation that suggests that the rings were responsible for the primary interaction with the molecular target of the compounds in the parasite. The bivalent imidazolium and triazolium compounds disrupted the process whereby merozoites gain entry into erythrocytes, however, they did not appear to prevent merozoites from forming. The compounds were also found to be active in a murine Plasmodium berghei infection, a result consistent with the compounds specifically interacting with a parasite component that is required for replication and is conserved between two Plasmodium species. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.002

文献信息

• Terminal Alkyne Coupling Reactions Through a Ring: Effect of Ring Size on Rate and Regioselectivity
  作者：Caroline M. Storey、Matthew R. Gyton、Rhiann E. Andrew、Adrian B. Chaplin

  DOI：10.1002/chem.202002962

  日期：2020.11.17

  alkynyl alkenyl derivatives and produce rhodium(I) complexes of conjugated 1,3‐enynes by C−C bond reductive elimination through the annulus of the ancillary ligand. The intermediates are formed with orthogonal regioselectivity, with E‐alkenyl complexes derived from HC≡CtBu and gem‐alkenyl complexes derived from HC≡CAr’, and the reductive elimination step is appreciably affected by the ring size of the

  由基于大环 NHC 的钳形配体的铑 (I) 配合物促进的末端炔烃偶联反应，其特征是十二亚甲基、十四亚甲基或十六亚甲基翼尖连接体，即。[Rh(CNC-n)(C 2 H 4 )][BAr F 4 ] (n=12, 14, 16; Ar F =3,5-(CF 3 ) 2 C 6 H 3 )—已被研究，使用大炔烃 HC≡C t Bu 和 HC≡CAr' (Ar'=3,5‐ t Bu 2 C 6 H 3 ) 作为底物。这些化学计量反应继续形成铑(III)炔基烯基衍生物，并通过辅助配体的环通过CC键还原消除产生共轭1,3-烯炔的铑(I)络合物。中间体以正交区域选择性形成，其中E-烯基配合物衍生自HC≡C t Bu，gem-烯基配合物衍生自HC≡CAr'，并且还原消除步骤明显受到大环环尺寸的影响。对于 HC−C t Bu的自偶联，E ‐ t BuC−CCH=CH t Bu 是通过相应的铑 (III) 炔基E
• Bis-imidazoles as molecular probes for peripheral sites of the zinc endopeptidase of botulinum neurotoxin serotype A
  作者：Isidro Merino、Jason D. Thompson、Charles B. Millard、James J. Schmidt、Yuan-Ping Pang

  DOI：10.1016/j.bmc.2006.01.015

  日期：2006.5

  Botulinum neurotoxin serotype A (BoNTA) is highly toxic, and its antidote is currently unavailable. The essential light-chain subunit of BoNTA is a zinc endopeptidase that can be used as a target for developing antidotes. However, the development of high-affinity, small-molecule inhibitors of the endopeptidase is as challenging as the development of small-molecule inhibitors of protein-protein complexation. This is because the polypeptide substrate wraps around the circumference of the endopeptidase upon binding, thereby constituting an unusually large substrate-enzyme interface of 4840 angstrom(2). To overcome the large-interface problem, we propose using the zinc-coordination and bivalence approaches to design inhibitors of BoNTA. Here we report the development of alkylene-linked bis-imidazoles that inhibit the endopeptidase in a two-site binding mode, The bis-imidazole tethered with 13 methylene groups, the most potent of the alkylene-linked dimers, showed 61% inhibition of the zinc endopeptidase of BoNTA at a concentration of 100 mu M. The results demonstrate the presence of a peripheral binding site for an imidazolium group at the rim of the BoNTA active-site cleft. This peripheral site enables the use of the bivalence approach to improve Our previously reported small-molecule inhibitors that were developed according to the zinc-coordination approach. (c) 2006 Elsevier Ltd All rights reserved.
• The anti-malarial activity of bivalent imidazolium salts
  作者：Jason Z. Vlahakis、Simona Mitu、Gheorghe Roman、E. Patricia Rodriguez、Ian E. Crandall、Walter A. Szarek

  DOI：10.1016/j.bmc.2011.06.002

  日期：2011.11

  A series of compounds containing bivalent imidazolium rings and one triazolium analog were synthesized and evaluated for their ability to inhibit the replication of Plasmodium falciparum cultures. The activity and selectivity of the compounds for P. falciparum cultures were found to depend on the presence of electron-deficient rings that were spaced an appropriate distance apart. The activity of the compounds was not critically dependent on the nature of the linker between the electron-deficient rings, an observation that suggests that the rings were responsible for the primary interaction with the molecular target of the compounds in the parasite. The bivalent imidazolium and triazolium compounds disrupted the process whereby merozoites gain entry into erythrocytes, however, they did not appear to prevent merozoites from forming. The compounds were also found to be active in a murine Plasmodium berghei infection, a result consistent with the compounds specifically interacting with a parasite component that is required for replication and is conserved between two Plasmodium species. (C) 2011 Elsevier Ltd. All rights reserved.
• Activation of a Copper Biscarbene Mechano‐Catalyst Using Single‐Molecule Force Spectroscopy Supported by Quantum Chemical Calculations
  作者：Matthew S. Sammon、Michel Biewend、Philipp Michael、Simone Schirra、Milan Ončák、Wolfgang H. Binder、Martin K. Beyer

  DOI：10.1002/chem.202100555

  日期：2021.6.16

  2.6 nN at room temperature in dimethyl sulfoxide. The average length-increase upon rupture of the Cu−C bond, due to the stretching of the safety line, agrees with quantum chemical calculations, but the values exhibit an unusual scattering. This scattering was assigned to the conformational flexibility of the mechanophore, which includes formation of a threaded structure and recoiling of the safety line

  单分子力谱可以研究机械力对单个键的影响。通过确定充分激活键以引发解离所需的力，可以预测机械载体的行为。测量了激活用于自修复材料的铜双卡宾机械催化剂所需的力。通过使用绕过机械载体的安全线，可以精确定位所研究的键的解离，并确定室温下二甲亚砜中的断裂力范围为 1.6 至 2.6 nN。由于安全线的拉伸，Cu−C 键断裂时的平均长度增加与量子化学计算一致，但这些值表现出不寻常的散射。这种散射归因于机械载体的构象灵活性，其中包括螺纹结构的形成和安全线的反冲。