2-乙炔-1-[[2-(三甲基甲硅烷基)乙氧基]甲基]-1H-咪唑 | 448299-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-乙炔-1-[[2-(三甲基甲硅烷基)乙氧基]甲基]-1H-咪唑
• 英文名称: 1-{[2-(trimethylsilyl)ethoxy]methyl}-2-ethynylimidazole
• 英文别名: 2-Ethynyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole；2-[(2-ethynylimidazol-1-yl)methoxy]ethyl-trimethylsilane
• CAS: 448299-38-5
• 化学式: C₁₁H₁₈N₂OSi
• 分子量: 222.362
• InChiKey: VGHALEHDGOUHRX-UHFFFAOYSA-N

物化性质

• 沸点：
  305.4±48.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙炔-1-[[2-(三甲基甲硅烷基)乙氧基]甲基]-1H-咪唑 在 三氟乙酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl)-2-ethynylimidazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent

  摘要：

  To explore more potent N-acylimidazole analogues of CDDO than CDDO-Im, which is one of the most potent compounds in several widely used bioassays related to protection against inflammation and carcinogenesis; we have synthesized and evaluated five new N-acyl(acetylenic) imidazole analogues. Among them, 4-ethynylimidazole 4 is nearly equivalent to CDDO-Im in potency in these bioassays. Remarkably, the solid form of 4 is more stable than that of CDDO-Im. These findings suggest that 4 is a very promising anti-inflammatory and cytoprotective agent and its further preclinical evaluation is warranted. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.018
• 作为产物：
  描述：

  2-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 水 、 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 42.0h， 生成 2-乙炔-1-[[2-(三甲基甲硅烷基)乙氧基]甲基]-1H-咪唑
  参考文献：
  名称：

  4-[（2-亚氨基并乙炔基）]-5-（2-吡啶基乙炔基）藜的合成及与银（I）和钯（II）的配位化合物的表征

  摘要：

  摘要我们描述了配体4-[（（2-咪唑基乙炔基）]-5-（2-吡啶基乙炔基）杂芳基及其与银（I）和钯（II）的配位配合物的设计，合成和表征。1 H NMR滴定清楚地表明两种阳离子均形成1：1配位络合物。二氯化钯配合物的X射线结构证实了钯（II）的反式配位，三氟甲磺酸银配合物证实了关于银（I）的线性配位的几何形状。下载：下载高分辨率图像（74KB）下载：下载完整尺寸的图像

  DOI：

  10.1016/j.ica.2019.119328

文献信息

• Synthesis of 4-[(2-imidazylethynyl)]-5-(2-pyridylethynyl)veratrole and characterization of the coordination complexes with silver(I) and palladium(II)
  作者：Chideraa I. Nwachukwu、Eric Bosch

  DOI：10.1016/j.ica.2019.119328

  日期：2020.3

  as well its coordination complexes with silver(I) and palladium(II). 1H NMR titration clearly indicates that 1:1 coordination complexes are formed with both cations. The X-ray structure of the palladium dichloride complex confirms the trans coordination of palladium(II) and the silver trifluoromethanesulfonate complex confirms the linear coordination geometry about silver(I). Download : Download high-res

  摘要我们描述了配体4-[（（2-咪唑基乙炔基）]-5-（2-吡啶基乙炔基）杂芳基及其与银（I）和钯（II）的配位配合物的设计，合成和表征。1 H NMR滴定清楚地表明两种阳离子均形成1：1配位络合物。二氯化钯配合物的X射线结构证实了钯（II）的反式配位，三氟甲磺酸银配合物证实了关于银（I）的线性配位的几何形状。下载：下载高分辨率图像（74KB）下载：下载完整尺寸的图像
• Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent
  作者：Tadashi Honda、Albena T. Dinkova-Kostova、Emilie David、Eric M. Padegimas、Chitra Sundararajan、Melean Visnick、Ron Bumeister、W. Christian Wigley

  DOI：10.1016/j.bmcl.2011.03.018

  日期：2011.4

  To explore more potent N-acylimidazole analogues of CDDO than CDDO-Im, which is one of the most potent compounds in several widely used bioassays related to protection against inflammation and carcinogenesis; we have synthesized and evaluated five new N-acyl(acetylenic) imidazole analogues. Among them, 4-ethynylimidazole 4 is nearly equivalent to CDDO-Im in potency in these bioassays. Remarkably, the solid form of 4 is more stable than that of CDDO-Im. These findings suggest that 4 is a very promising anti-inflammatory and cytoprotective agent and its further preclinical evaluation is warranted. (C) 2011 Elsevier Ltd. All rights reserved.