5-phenyl-3,4-dihydro 2H pyrrole-2,2-dicarboxylate de diethyle | 2851-46-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-phenyl-3,4-dihydro 2H pyrrole-2,2-dicarboxylate de diethyle
• 英文别名: diethyl 5-phenyl-3,4-dihydro-2H-pyrrole-2,2-dicarboxylate；Diethyl 5-phenyl-3,4-dihydropyrrole-2,2-dicarboxylate
• CAS: 2851-46-9
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: NMDZOZFZGUXLBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-phenyl-3,4-dihydro 2H pyrrole-2,2-dicarboxylate de diethyle 在 四氯苯醌 作用下， 以 xylene 为溶剂， 生成 5-phenyl pyrrole-1,2-dicarboxylate de diethyle 、 5-phenyl pyrrole-2,3-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
• 作为产物：
  描述：

  苯乙酮 以 硝基苯 、 苯 为溶剂， 反应 0.5h， 生成 5-phenyl-3,4-dihydro 2H pyrrole-2,2-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

• [1+1+3] Annulation of Diazoenals and Vinyl Azides: Direct Synthesis of Functionalized 1‐Pyrrolines through Olefination
  作者：Vinaykumar Kanchupalli、Sreenivas Katukojvala

  DOI：10.1002/anie.201801976

  日期：2018.5.4

  A dirhodium carboxylate catalyzed [1+1+3] annulation reaction of diazoenals and vinyl azides that gives synthetically important enal‐functionalized 1‐pyrroline derivatives was developed. The reaction involves a novel rhodium‐catalyzed olefination of diazoenals with vinyl azides via electrophilic enal carbenoids, resulting in a new class of enal acrylates. The annulation reaction was used for the direct

  开发了一种由羧酸重氮催化的重氮烯醛和乙烯基叠氮化物的[1 + 1 + 3]环化反应，该反应可提供合成上重要的烯丙基官能化的1-吡咯啉衍生物。该反应涉及通过亲电子的烯类化合物通过重氮与乙烯基叠氮化物进行铑催化的新型的重氮烯醛烯化反应，从而产生了一类新的烯丙基丙烯酸酯。环化反应用于直接合成有价值的氘代1-吡咯啉。烯醛官能化的1-吡咯啉的结构多样化导致多环生物碱中存在生物学上重要的吡咯烷融合的恶唑烷，氨基酸衍生物和6-氮杂双环[3.2.1]辛烷基序。
• 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：——