3,5-diphenyl-3,4-dihydro 2H pyrrole-2-carboxylate d'ethyle | 134753-47-2

• 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: 3,5-diphenyl-3,4-dihydro 2H pyrrole-2-carboxylate d'ethyle
• 英文别名: 3,5-diphenyl-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester；3,5-Diphenyl-3,4-dihydro-2H-pyrrol-2-carbonsaeure-aethylester；ethyl 3,5-diphenyl-3,4-dihydro-2H-pyrrole-2-carboxylate
• CAS: 134753-47-2
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: SDTMMOBIVBFZEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-diphenyl-3,4-dihydro 2H pyrrole-2-carboxylate d'ethyle 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 以58%的产率得到ethyl 3,5-diphenyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  One-Pot Synthesis of Pyrrole-2-carboxylates and -carboxamides via an Electrocyclization/Oxidation Sequence

  摘要：

  An electrocyclic ring closure is the key step of an efficient one-pot method for the synthesis of pyrrole-2-carboxylates and -carboxamides from chalcones and glycine esters or amides. The 3,4-dihydro-2H-pyrrole intermediates generated in situ are oxidized to the corresponding pyrroles by stoichiometric oxidants or by catalytic copper(II) and air in moderate to high yields. A wide range of functional groups are tolerated, and further combination with an in situ bromination gives access to polyfunctional pyrrole scaffolds.

  DOI：

  10.1021/jo5021823
• 作为产物：
  描述：

  2-nitro-5-oxo-3,5-diphenylpentanoic acid ethyl ester 在 甲醇 、 palladium on activated charcoal 作用下， 生成 3,5-diphenyl-3,4-dihydro 2H pyrrole-2-carboxylate d'ethyle
  参考文献：
  名称：

  460.查耳酮和相关化合物。第五部分在查耳酮中添加硝基化合物

  摘要：

  DOI：

  10.1039/jr9580002276

文献信息

• 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.
• 460. Chalcones and related compounds. Part V. Addition of nitro-compounds to chalcones
  作者：W. Davey、D. J. Tivey

  DOI：10.1039/jr9580002276

  日期：——
• One-Pot Synthesis of Pyrrole-2-carboxylates and -carboxamides via an Electrocyclization/Oxidation Sequence
  作者：Dennis Imbri、Natalie Netz、Murat Kucukdisli、Lisa Marie Kammer、Philipp Jung、Annika Kretzschmann、Till Opatz

  DOI：10.1021/jo5021823

  日期：2014.12.5

  An electrocyclic ring closure is the key step of an efficient one-pot method for the synthesis of pyrrole-2-carboxylates and -carboxamides from chalcones and glycine esters or amides. The 3,4-dihydro-2H-pyrrole intermediates generated in situ are oxidized to the corresponding pyrroles by stoichiometric oxidants or by catalytic copper(II) and air in moderate to high yields. A wide range of functional groups are tolerated, and further combination with an in situ bromination gives access to polyfunctional pyrrole scaffolds.