3,5-diphenyl pyrrole-1,2-dicarboxylate de diethyle | 91307-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,5-diphenyl pyrrole-1,2-dicarboxylate de diethyle
• 英文别名: Diethyl 3,5-diphenyl-1H-pyrrole-1,2-dicarboxylate；diethyl 3,5-diphenylpyrrole-1,2-dicarboxylate
• CAS: 91307-93-6
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: AWVQWUVIEJKSLN-UHFFFAOYSA-N

物化性质

• 沸点：
  541.7±60.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-diphenyl pyrrole-1,2-dicarboxylate de diethyle 以 二甲基亚砜 为溶剂， 反应 2.0h， 以70%的产率得到ethyl 3,5-diphenyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Dérivés arylés et éthoxycarbonylés de 3,4-dihydro 2H pyrrole, 2H pyrrole et pyrrole immunoactifs sur le lymphocyte T humain

  摘要：

  Several pyrroles, 2H pyrroles, 3,3-dihydropyrroles substituted in various positions with phenyl and ethoxycarbonyl groups, were prepared in order to study in vitro their immunoactivity on human T lymphocytes. The best action was observed when on the pyrrole cycle, a carboxylic chain in position 2, an aromatic cycle in 5, and a substituent in 3, particularly a phenyl or a carboxylic ester were simultaneously found to exist. A conformational approach, performed by magnetic anisotropy quantification of phenyls, using Johnson and Bovey increments, showed that the orthogonality of the substituent in 3 is important as regards the pyrrolic cycle. Thus, the ethyl 3,5-diphenylpyrrole-2-carboxylate ester 8 appears to be the most interesting as it is more efficient than the levamisole chlorhydrate in the tests connected with the lymphoblastic transformation in presence of PHA (phytohemaglutinin) and related to the mobilisation of CD2 receptors.

  DOI：

  10.1016/0223-5234(91)90217-b
• 作为产物：
  描述：

  3,5-diphenyl 2H pyrrole-2,2-dicarboxylate de diethyle 以 xylene 为溶剂， 反应 1.0h， 以90%的产率得到3,5-diphenyl pyrrole-1,2-dicarboxylate de diethyle
  参考文献：
  名称：

  Dérivés arylés et éthoxycarbonylés de 3,4-dihydro 2H pyrrole, 2H pyrrole et pyrrole immunoactifs sur le lymphocyte T humain

  摘要：

  Several pyrroles, 2H pyrroles, 3,3-dihydropyrroles substituted in various positions with phenyl and ethoxycarbonyl groups, were prepared in order to study in vitro their immunoactivity on human T lymphocytes. The best action was observed when on the pyrrole cycle, a carboxylic chain in position 2, an aromatic cycle in 5, and a substituent in 3, particularly a phenyl or a carboxylic ester were simultaneously found to exist. A conformational approach, performed by magnetic anisotropy quantification of phenyls, using Johnson and Bovey increments, showed that the orthogonality of the substituent in 3 is important as regards the pyrrolic cycle. Thus, the ethyl 3,5-diphenylpyrrole-2-carboxylate ester 8 appears to be the most interesting as it is more efficient than the levamisole chlorhydrate in the tests connected with the lymphoblastic transformation in presence of PHA (phytohemaglutinin) and related to the mobilisation of CD2 receptors.

  DOI：

  10.1016/0223-5234(91)90217-b

文献信息

• Sammes, Michael P.; Chung, Margaret W. L.; Katritzky, Alan R., Journal of the Chemical Society. Perkin transactions I, 1985, p. 1773 - 1780
  作者：Sammes, Michael P.、Chung, Margaret W. L.、Katritzky, Alan R.

  DOI：——

  日期：——
• BIROUK, M.;HARRAGA, S.;PANOUSE-PERRIN, J.;ROBERT, J. F.;DAMELINCOURT, M.;+, EUR. J. MED. CHEM., 26,(1991) N, C. 91-99
  作者：BIROUK, M.、HARRAGA, S.、PANOUSE-PERRIN, J.、ROBERT, J. F.、DAMELINCOURT, M.、+

  DOI：——

  日期：——
• SAMMES, M. P.;CHUNG, M. W. L.;KATRITZKY, A. R., J. CHEM. SOC. PERKIN TRANS., 1985, N 8, 1773-1779
  作者：SAMMES, M. P.、CHUNG, M. W. L.、KATRITZKY, A. R.

  DOI：——

  日期：——
• Dérivés arylés et éthoxycarbonylés de 3,4-dihydro 2H pyrrole, 2H pyrrole et pyrrole immunoactifs sur le lymphocyte T humain
  作者：M Birouk、S Harraga、J Panouse-Perrin、JF Robert、M Damelincourt、F Theobald、R Mercier、JJ Panouse

  DOI：10.1016/0223-5234(91)90217-b

  日期：1991.1

  Several pyrroles, 2H pyrroles, 3,3-dihydropyrroles substituted in various positions with phenyl and ethoxycarbonyl groups, were prepared in order to study in vitro their immunoactivity on human T lymphocytes. The best action was observed when on the pyrrole cycle, a carboxylic chain in position 2, an aromatic cycle in 5, and a substituent in 3, particularly a phenyl or a carboxylic ester were simultaneously found to exist. A conformational approach, performed by magnetic anisotropy quantification of phenyls, using Johnson and Bovey increments, showed that the orthogonality of the substituent in 3 is important as regards the pyrrolic cycle. Thus, the ethyl 3,5-diphenylpyrrole-2-carboxylate ester 8 appears to be the most interesting as it is more efficient than the levamisole chlorhydrate in the tests connected with the lymphoblastic transformation in presence of PHA (phytohemaglutinin) and related to the mobilisation of CD2 receptors.