5-甲基-2-苯基-3H-咪唑-4-羧酸乙酯 | 77335-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-甲基-2-苯基-3H-咪唑-4-羧酸乙酯
• 英文名称: ethyl 4-methyl-2-phenyl-1H-imidazole-5-carboxylate
• 英文别名: 4-carbethoxy-5-methyl-2-phenylimidazole；ethyl 5-methyl-2-phenyl-1H-imidazole-4-carboxylate
• CAS: 77335-93-4
• 化学式: C₁₃H₁₄N₂O₂
• mdl: MFCD09759050
• 分子量: 230.266
• InChiKey: NBVIVZIQTRTTBY-UHFFFAOYSA-N

物化性质

• 熔点：
  199-199.5 °C
• 沸点：
  416.9±25.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  5-甲基-2-苯基-3H-咪唑-4-羧酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以57%的产率得到1H-咪唑,4,5-二甲基-2-苯基-
  参考文献：
  名称：

  Biomimetic models for cysteine proteases. 1. Intramolecular imidazole catalysis of thiol ester solvolysis: a model for the deacylation step

  摘要：

  DOI：

  10.1021/ja00307a043
• 作为产物：
  描述：

  N-苯甲酰基-DL-丙氨酸 在 三丁基膦 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 5-甲基-2-苯基-3H-咪唑-4-羧酸乙酯
  参考文献：
  名称：

  Synthesis of Di- and Tri-Substituted Imidazole-4-carboxylates via PBu₃-Mediated [3 + 2] Cycloaddition

  摘要：

  Some new di- and trisubstituted imidazole-4-carboxylates were prepared from amidoacetic acids 3 in the present report. The key step to establish such imidazole-4-carboxylates stemmed from the PBu3-mediated [3+2] cycloaddition between in situ-generated 2-oxazolinone 4 and ethyl cyanoformate6. Our results indicated that trisubstituted imidazoles 7-20 were afforded in better yields than those of disubstituted imidazoles 21-27. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.644846

文献信息

• [EN] AROMATIC HETEROCYCLIC DERIVATIVE HAVING TRPV4-INHIBITING ACTIVITY<br/>[FR] DÉRIVÉ AROMATIQUE HÉTÉROCYCLIQUE PRÉSENTANT UNE ACTIVITÉ INHIBITRICE DE TRPV4
  申请人：SHIONOGI & CO

  公开号：WO2012144661A1

  公开（公告）日：2012-10-26

  A compound having TRPV4 inhibitory activity or a pharmaceutically acceptable salt thereof is provided. The present invention is related to a compound represented by the formula (I). wherein R1a is substituted or unsubstituted alkyl or the like; R1b is hydrogen or substituted or unsubstituted alkyl; R1c is hydrogen, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted nonaromatic heterocyclic group or the like; -L- is -C(=0)-NR2- or the like; X is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or the like, or a pharmaceutically acceptable salt thereof.

  提供具有TRPV4抑制活性的化合物或其药用可接受的盐。本发明涉及一种由式(I)表示的化合物。其中R1a是取代或未取代的烷基或类似物；R1b是氢或取代或未取代的烷基；R1c是氢、卤素、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的非芳香杂环基或类似物；-L-是-C(=0)-NR2-或类似物；X是取代或未取代的芳基、取代或未取代的杂芳基或类似物，或其药用可接受的盐。
• 400. Synthesis of a 4-cyano-oxazole
  作者：J. W. Cornforth、H. T. Huang

  DOI：10.1039/jr9480001969

  日期：——
• Veronese, A.C.; Cavicchioni, G.; Servadio, G., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1723 - 1725
  作者：Veronese, A.C.、Cavicchioni, G.、Servadio, G.、Vecchiati, G.

  DOI：——

  日期：——
• Discovery of cell-active phenyl-imidazole Pin1 inhibitors by structure-guided fragment evolution
  作者：Andrew Potter、Victoria Oldfield、Claire Nunns、Christophe Fromont、Stuart Ray、Christopher J. Northfield、Christopher J. Bryant、Simon F. Scrace、David Robinson、Natalia Matossova、Lisa Baker、Pawel Dokurno、Allan E. Surgenor、Ben Davis、Christine M. Richardson、James B. Murray、Jonathan D. Moore

  DOI：10.1016/j.bmcl.2010.09.063

  日期：2010.11

  Pin1 is an emerging oncology target strongly implicated in Ras and ErbB2-mediated tumourigenesis. Pin1 isomerizes bonds linking phospho-serine/threonine moieties to proline enabling it to play a key role in proline-directed kinase signalling. Here we report a novel series of Pin1 inhibitors based on a phenyl imidazole acid core that contains sub-mu M inhibitors. Compounds have been identified that block prostate cancer cell growth under conditions where Pin1 is essential. (C) 2010 Elsevier Ltd. All rights reserved.
• ZnCl₂-Catalyzed [3 + 2] Cycloaddition of Benzimidates and 2<i>H</i>-Azirines for the Synthesis of Imidazoles
  作者：Shoujie Shi、Kang Xu、Cheng Jiang、Zhenhua Ding

  DOI：10.1021/acs.joc.8b02437

  日期：2018.12.7

  ZnCl2-catalyzed [3 + 2] cycloaddition reaction of benzimidates and 2H-azirines has been developed. This convenient method allowed the efficient construction of a series of multisubstituted imidazoles in moderate to good yields under mild reaction conditions. This transformation exhibits good reactivity and high functional group tolerance.