4-cyano-1-formyl-2,4,5,6-tetrahydro-4,6,6-tetramethylcyclopentapyrrole-3-carboxylic acid | 54609-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-cyano-1-formyl-2,4,5,6-tetrahydro-4,6,6-tetramethylcyclopentapyrrole-3-carboxylic acid
• 英文别名: 2-phenyl-1-formyl-3-carboxy-2,4,5,6-tetrahydro-4,6,6-trimethylcyclopenta[c]-pyrrole-4-carbonitrile；4-cyano-1-formyl-4,6,6-trimethyl-2-phenyl-5H-cyclopenta[c]pyrrole-3-carboxylic acid
• CAS: 54609-75-5
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: SWSJMZDATRRKMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-cyano-1-formyl-2,4,5,6-tetrahydro-4,6,6-tetramethylcyclopentapyrrole-3-carboxylic acid 在 硫酸 、 苯胺 、 2,3-二甲基苯胺 作用下， 反应 0.75h， 生成 2-phenyl-1-formyl-2,4,5,6-tetrahydro-4,6,6-trimethylcyclopenta[c]-pyrrole-4-carboxamide
  参考文献：
  名称：

  Experimental antiulcer drugs. 4. 1,3-Disubstituted 2,4,5,6-tetrahydro-4,6,6-trimethyl-2-phenylcyclopenta[c]pyrrole-4-carboxamides

  摘要：

  The synthesis of 1,3-disubstituted 2,4,5,6-tetrahydro-4,6,6-trimethyl-2-phenylcyclopenta[c]pyrrole-4-carboxamides is reported. The derivatives included R1 = R3 = H, R1 = CH2OH with R3 = H (16) or CH3, R1 = CH3 with R3 = CH2OH (17), and R1 = R3 = CH2OH. The monohydroxymethyl derivatives were as active as the parent cyclopentapyrrole, where R1 = R3 = CH3 (1), when administered orally in the pyloric ligated rat. The compounds lacking one or both CH3 groups at C-1 or C-3 were much less active. Compounds 16 and 17 inhibited histamine-induced gastric acid secretion in the dog.

  DOI：

  10.1021/jm00182a024
• 作为产物：
  描述：

  1-(dichloromethyl)-2-phenyl-2,4,5,6-tetrahydro-3-(trichloromethyl)-4,6,6-trimethylcyclopentapyrrole-4-carbonitrile 在 potassium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 2.5h， 以74%的产率得到4-cyano-1-formyl-2,4,5,6-tetrahydro-4,6,6-tetramethylcyclopentapyrrole-3-carboxylic acid
  参考文献：
  名称：

  Experimental antiulcer drugs. 4. 1,3-Disubstituted 2,4,5,6-tetrahydro-4,6,6-trimethyl-2-phenylcyclopenta[c]pyrrole-4-carboxamides

  摘要：

  The synthesis of 1,3-disubstituted 2,4,5,6-tetrahydro-4,6,6-trimethyl-2-phenylcyclopenta[c]pyrrole-4-carboxamides is reported. The derivatives included R1 = R3 = H, R1 = CH2OH with R3 = H (16) or CH3, R1 = CH3 with R3 = CH2OH (17), and R1 = R3 = CH2OH. The monohydroxymethyl derivatives were as active as the parent cyclopentapyrrole, where R1 = R3 = CH3 (1), when administered orally in the pyloric ligated rat. The compounds lacking one or both CH3 groups at C-1 or C-3 were much less active. Compounds 16 and 17 inhibited histamine-induced gastric acid secretion in the dog.

  DOI：

  10.1021/jm00182a024

文献信息

• OESTERLIN R.; BELL M. R.; HLAVAC A. G.; MCGARRY A. G.; GELOTTE K. O.; BRA+, J. MED. CHEM., 1980, 23, NO 8, 945-948
  作者：OESTERLIN R.、 BELL M. R.、 HLAVAC A. G.、 MCGARRY A. G.、 GELOTTE K. O.、 BRA+

  DOI：——

  日期：——
• US4008250A
  申请人：——

  公开号：US4008250A

  公开（公告）日：1977-02-15
• US4098797A
  申请人：——

  公开号：US4098797A

  公开（公告）日：1978-07-04
• US4140854A
  申请人：——

  公开号：US4140854A

  公开（公告）日：1979-02-20
• US4239687A
  申请人：——

  公开号：US4239687A

  公开（公告）日：1980-12-16