2-(4-methoxyphenyl)-1H-4-imidazolcarbaldehyde | 97749-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-methoxyphenyl)-1H-4-imidazolcarbaldehyde
• 英文别名: 4-formyl-2-(4-methoxyphenyl)-1H-imidazole；2-(4-methoxyphenyl)-1H-imidazole-4(5)-carbaldehyde；2-(4-Methoxyphenyl)-1H-imidazole-4-carbaldehyde；2-(4-methoxyphenyl)-1H-imidazole-5-carbaldehyde
• CAS: 97749-71-8
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: JKVTUMUVHCCEBR-UHFFFAOYSA-N

物化性质

• 熔点：
  >240 °C
• 沸点：
  446.7±25.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-1H-4-imidazolcarbaldehyde 在 氢溴酸 作用下， 反应 15.0h， 以40.7%的产率得到2-(4-hydroxyphenyl)-1H-imidazole-4(5)-carbaldehyde
  参考文献：
  名称：

  13C CPMAS NMR 作为克服快速互变异构效应的 2-苯基取代咪唑的完整结构描述的工具

  摘要：

  迄今为止，尚未详细研究 2-苯基咪唑甲醛的互变异构化，尽管该过程对于咪唑衍生物来说是众所周知的现象。这就是为什么我们将研究重点放在一系列 2-苯基咪唑甲醛及其母体醇上，这些醇在溶液和固态下通过详细的 1H 和 13C NMR 合成和研究。明显的问题是快速互变异构阻碍了通过常规 13C NMR 测量对化合物的完整结构描述。事实上，溶液中的 13C NMR 光谱显示出较差的分辨率，并且在大多数情况下，无法检测到来自咪唑环的信号。为了避免这个问题，我们使用 13C CP-MAS NMR 作为替代光谱方法，用于对所研究的 2-苯基咪唑系列进行明确的光谱表征。通过考虑互变异构过程和分子间相互作用，结合量子化学DFT-GIAO方法对数据进行了分析。DFT (B3LYP/6-31G(d,p)) 计算允许识别和建议气相和 DMSO 溶剂中的优选互变异构体，对于醇类是（2-苯基-1H-咪唑-4-基）甲醇及其类似物，醛类是

  DOI：

  10.3390/molecules25173770
• 作为产物：
  描述：

  2-(4-methoxyphenyl)-1H-imidazole-4-carboxylic acid 在 lithium aluminium tetrahydride 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 2-(4-methoxyphenyl)-1H-4-imidazolcarbaldehyde
  参考文献：
  名称：

  Synthesis, Structure, and Neuroprotective Properties of Novel Imidazolyl Nitrones

  摘要：

  A new series of imidazolyl nitrones spin traps has been synthesized and evaluated pharmacologically. The salient structural feature of these molecules is the presence of an imidazole moiety substituted by aromatic or heteroaromatic cycles. This connectivity imparts to the nitrone superior neuroprotective properties in vivo and in parallel reduced side effects and toxicity. Thus compound 6a (a 2-phenylimidazolyl nitrone) administered intraperitoneally protects (80%) mice from lethality induced by an intracerebroventricular administration of tert-butyl hydroperoxide (t-BHP) an oxidant capable of inducing neurodegenerative processes. Administration of the archetypal nitrone phenyl-tert-butyl nitrone (PBN) at an equimolar dose also affords some protection (60%) in this test. However, this activity is accompanied by hypothermia, whereas no such effect is apparent for 6a. Moreover, previously prepared nonsubstituted or alkyl-substituted imidazolyl nitrones were shown to be extremely toxic to rats in contrast to the compounds prepared in this study. The observed activities in vivo correlate well with the calculated partition coefficients (ClogP) and HOMO energy level.

  DOI：

  10.1021/jm991154w

文献信息

• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。
• Imidazo[1,5-d][1,2,4]triazines as potential antiasthma agents
  作者：Rolf Paul、John A. Brockman、W. A. Hallett、John W. Hanifin、M. Ernestine Tarrant、Lawrence W. Torley、Francis M. Callahan、Paul F. Fabio、Bernard D. Johnson

  DOI：10.1021/jm00149a029

  日期：1985.11

  By using inhibition of histamine release from antigen-challenged, sensitized human basophils as a means of identifying a potentially prophylactic drug for the treatment of asthma, a series of substituted imidazo[1,5-d][1,2,4]triazines were found, which were active. These compounds were prepared by treating imidazolecarboxaldehydes with excess Grignard agent and then oxidizing the resulting alcohols to ketones with Jones reagent. Pyrolysis of a mixture of ketone and methyl carbazate at 200 degrees C in diphenyl ether produced the desired imidazo[1,5-d][1,2,4]triazines. Those compounds with the greatest basophil activity were tested for in vivo activity in the mouse passive cutaneous anaphylaxis (PCA) and the guinea pig passive anaphylaxis tests. The best compounds, 1-ethyl-8-methyl-6-propylimidazo[1,5-d][1,2,4]triazin-4(3H)- one (4-17) and 1,8-dimethyl-6-propylimidazo[1,5-d][1,2,4]triazin-4-(3H)-one (4-16) were chosen for further study.
• Highly Efficient, Environment-Friendly, One-Pot Synthesis of 2-Substituted 4-Formylimidazoles from 4-Acylaminoisoxazoles
  作者：Feng Gao、Xin-Chuan Tian、Xiao-Xia Qu、Dan Wang、Dong Pu

  DOI：10.1055/s-0034-1379201

  日期：——

  A highly efficient and environment-friendly one-pot synthesis of 2-substituted 4-formylimidazoles was accomplished. Raney nickel catalyzed hydrogenation of 4-acylaminoisoxazoles in ethanol, followed by sodium hydroxide promoted recyclization of the ring-opened intermediates, afforded the functionalized imidazoles.
• Nouveaux dérivés de nitrone, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：LES LABORATOIRES SERVIER

  公开号：EP0967207B1

  公开（公告）日：2002-09-11
• PAUL, R.;BROCKMAN, J. A.;HALLETT, W. A.;HANIFIN, J. W.;TARRANT, M. E.;TOR+, J. MED. CHEM., 1985, 28, N 11, 1704-1716
  作者：PAUL, R.、BROCKMAN, J. A.、HALLETT, W. A.、HANIFIN, J. W.、TARRANT, M. E.、TOR+

  DOI：——

  日期：——