1-(2,6-dimethylphenyl)-1H-pyrrole-2-carbaldehyde | 30186-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2,6-dimethylphenyl)-1H-pyrrole-2-carbaldehyde
• 英文别名: 1-(2,6-dimethyl-phenyl)-pyrrole-2-carbaldehyde；1-(2,6-dimethylphenyl)pyrrole-2-carbaldehyde
• CAS: 30186-42-6
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: IXTDGHYGOQZUFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,6-dimethylphenyl)-1H-pyrrole-2-carbaldehyde 在 sodium tetrahydroborate 、 potassium hydroxide 作用下， 以 二氯甲烷 、 乙二醇甲醚 、 异丙醇 为溶剂， 生成 (E)-2-{[1-(2,6-dimethylphenyl)-1H-pyrrol-2-yl]-methylidene}allobetulin
  参考文献：
  名称：

  Synthesis of pyrrol-2-yl- and pyrazol-4-ylmethylidene derivatives of betulin and allobetulin

  摘要：

  Aldol-crotonic condensation of allobetulone and betulonic aldehyde with N-substituted pyrrole-2- and pyrazole-4-carbaldehydes afforded a series of new alpha,beta-unsaturated ketones of lupane series. Their reduction provided 2-ylidene derivatives of allobetulin and betulin, potential chiral components of liquid crystal materials. Structures of 1-phenyl-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbaldehyde, (E)-2-{[3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}allobetulone, (E)-2-{[3-(4-bromophenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}-3-oxolup-20(29)-ene-28-carbaldehyde, (E)-2-{[3-(4-bromo-phenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}allobetulin, and (E)-2-{[3-(4-bromophe-nyl)-1-phenyl-1H-pyrazol-4-yl]-methylidene}lup-20(29)-ene-3,28-diol were established by X-ray diffraction (XRD) study.

  DOI：

  10.1134/s1070428015050231
• 作为产物：
  描述：

  2,6-二甲基苯胺 在 溶剂黄146 、 三氯氧磷 作用下， 生成 1-(2,6-dimethylphenyl)-1H-pyrrole-2-carbaldehyde
  参考文献：
  名称：

  Synthesis of pyrrol-2-yl- and pyrazol-4-ylmethylidene derivatives of betulin and allobetulin

  摘要：

  Aldol-crotonic condensation of allobetulone and betulonic aldehyde with N-substituted pyrrole-2- and pyrazole-4-carbaldehydes afforded a series of new alpha,beta-unsaturated ketones of lupane series. Their reduction provided 2-ylidene derivatives of allobetulin and betulin, potential chiral components of liquid crystal materials. Structures of 1-phenyl-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbaldehyde, (E)-2-{[3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}allobetulone, (E)-2-{[3-(4-bromophenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}-3-oxolup-20(29)-ene-28-carbaldehyde, (E)-2-{[3-(4-bromo-phenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}allobetulin, and (E)-2-{[3-(4-bromophe-nyl)-1-phenyl-1H-pyrazol-4-yl]-methylidene}lup-20(29)-ene-3,28-diol were established by X-ray diffraction (XRD) study.

  DOI：

  10.1134/s1070428015050231

文献信息

• Direct and Efficient Synthesis of Pyrrole-3-carbaldehydes by Vilsmeier-Haack Formylation of Pyrroles with Sterically Crowded Amides
  作者：Mikhail Kuznetsov、Petr Ilyin、Alena Pankova

  DOI：10.1055/s-0031-1290763

  日期：2012.5

  Abstract A simple and convenient synthetic method to prepare N-substituted pyrrole-3-carbaldehydes by Vilsmeier–Haack formylation of pyrroles using sterically crowded formamides was developed. The dependence of the formylation regioselectivity on steric features of substrates and reagents is discussed. A simple and convenient synthetic method to prepare N-substituted pyrrole-3-carbaldehydes by Vilsmeier–Haack

  摘要 开发了一种简单方便的合成方法，该方法通过使用空间拥挤的甲酰胺，通过Vilsmeier-Haack对吡咯进行甲酰化来制备N-取代的吡咯3-甲醛。讨论了甲酰化区域选择性对底物和试剂空间特征的依赖性。 开发了一种简单方便的合成方法，该方法通过使用空间拥挤的甲酰胺，通过Vilsmeier-Haack对吡咯进行甲酰化来制备N-取代的吡咯3-甲醛。讨论了甲酰化区域选择性对底物和试剂空间特征的依赖性。
• Synthesis of pyrrol-2-yl- and pyrazol-4-ylmethylidene derivatives of betulin and allobetulin
  作者：N. L. Babak、A. N. Semenenko、I. M. Gella、V. I. Musatov、S. V. Shishkina、N. B. Novikova、D. S. Sofronov、D. A. Morina、V. V. Lipson

  DOI：10.1134/s1070428015050231

  日期：2015.5

  Aldol-crotonic condensation of allobetulone and betulonic aldehyde with N-substituted pyrrole-2- and pyrazole-4-carbaldehydes afforded a series of new alpha,beta-unsaturated ketones of lupane series. Their reduction provided 2-ylidene derivatives of allobetulin and betulin, potential chiral components of liquid crystal materials. Structures of 1-phenyl-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbaldehyde, (E)-2-[3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}allobetulone, (E)-2-[3-(4-bromophenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}-3-oxolup-20(29)-ene-28-carbaldehyde, (E)-2-[3-(4-bromo-phenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}allobetulin, and (E)-2-[3-(4-bromophe-nyl)-1-phenyl-1H-pyrazol-4-yl]-methylidene}lup-20(29)-ene-3,28-diol were established by X-ray diffraction (XRD) study.