4-(4-methoxyphenyl)-1-methyl-1H-imidazole-2-carboxylicacid | 1221265-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-methoxyphenyl)-1-methyl-1H-imidazole-2-carboxylicacid
• 英文别名: 4-(4-Methoxyphenyl)-1-methylimidazole-2-carboxylic acid
• CAS: 1221265-84-4
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: MVGNHKSFGXMWIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  481.6±47.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methylhex-1-en-3-ol 、 4-(4-methoxyphenyl)-1-methyl-1H-imidazole-2-carboxylicacid 在 4-二甲氨基吡啶 、 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 20.0h， 以74%的产率得到2-methylhex-1-en-3-yl 4-(4-methoxyphenyl)-1-methyl-1H-imidazole-2-carboxylate
  参考文献：
  名称：

  Amaranzoles B−F, Imidazole-2-carboxy Steroids from the Marine Sponge Phorbas amaranthus. C24-N- and C24-O-Analogues from a Divergent Oxidative Biosynthesis

  摘要：

  Five new steroidal imidazoles, amaranzoles B-F, were isolated from extracts of the marine sponge Phorbas amaranthus along with the known amaranzole A. The C24-N-(4-p-hydroxyphenyl)imidazol-5-yl constitution found in amaranzoles A, C, and D is replaced by a C24-O-(4-p-hydroxyphenyl)imidazole-2-carboxylate motif in amaranzoles B, E, and F. The structures were elucidated by interpretation of spectroscopic data. The C24 side chain configuration was assigned by synthesis of a model ester followed by chiroptical comparisons of its CD spectrum with that of an amaranzole B derivative.

  DOI：

  10.1021/jo1000324
• 作为产物：
  描述：

  methyl 4-(4-methoxyphenyl)-1-methyl-1H-imidazole-2-carboxylate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以79%的产率得到4-(4-methoxyphenyl)-1-methyl-1H-imidazole-2-carboxylicacid
  参考文献：
  名称：

  Amaranzoles B−F, Imidazole-2-carboxy Steroids from the Marine Sponge Phorbas amaranthus. C24-N- and C24-O-Analogues from a Divergent Oxidative Biosynthesis

  摘要：

  Five new steroidal imidazoles, amaranzoles B-F, were isolated from extracts of the marine sponge Phorbas amaranthus along with the known amaranzole A. The C24-N-(4-p-hydroxyphenyl)imidazol-5-yl constitution found in amaranzoles A, C, and D is replaced by a C24-O-(4-p-hydroxyphenyl)imidazole-2-carboxylate motif in amaranzoles B, E, and F. The structures were elucidated by interpretation of spectroscopic data. The C24 side chain configuration was assigned by synthesis of a model ester followed by chiroptical comparisons of its CD spectrum with that of an amaranzole B derivative.

  DOI：

  10.1021/jo1000324

文献信息

• Amaranzoles B−F, Imidazole-2-carboxy Steroids from the Marine Sponge <i>Phorbas amaranthus</i>. C24-<i>N</i>- and C24-<i>O</i>-Analogues from a Divergent Oxidative Biosynthesis
  作者：Brandon I. Morinaka、Joseph R. Pawlik、Tadeusz F. Molinski

  DOI：10.1021/jo1000324

  日期：2010.4.16

  Five new steroidal imidazoles, amaranzoles B-F, were isolated from extracts of the marine sponge Phorbas amaranthus along with the known amaranzole A. The C24-N-(4-p-hydroxyphenyl)imidazol-5-yl constitution found in amaranzoles A, C, and D is replaced by a C24-O-(4-p-hydroxyphenyl)imidazole-2-carboxylate motif in amaranzoles B, E, and F. The structures were elucidated by interpretation of spectroscopic data. The C24 side chain configuration was assigned by synthesis of a model ester followed by chiroptical comparisons of its CD spectrum with that of an amaranzole B derivative.