2,4,5,6-tetrahydro-1,3-diformyl-4,6,6-trimethyl-2-phenylcyclopentapyrrole-4-carbonitrile | 54649-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,4,5,6-tetrahydro-1,3-diformyl-4,6,6-trimethyl-2-phenylcyclopentapyrrole-4-carbonitrile
• 英文别名: 1,3-diformyl-4,6,6-trimethyl-2-phenyl-2,4,5,6-tetrahydro-cyclopenta[c]pyrrole-4-carbonitrile；2-phenyl-2,4,5,6-tetrahydro-1,3-diformyl-4,6,6-trimethylcyclopenta[c]pyrrole-4-carbonitrile；1,3-diformyl-4,6,6-trimethyl-2-phenyl-5H-cyclopenta[c]pyrrole-4-carbonitrile
• CAS: 54649-60-4
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: GCNSAAHHXNULFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,5,6-tetrahydro-1,3-diformyl-4,6,6-trimethyl-2-phenylcyclopentapyrrole-4-carbonitrile 在 硫酸 作用下， 生成 1,3-diformyl-4,6,6-trimethyl-2-phenyl-2,4,5,6-tetrahydro-cyclopenta[c]pyrrole-4-carboxylic acid amide
  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：

  1,3-bis(dichloromethyl)-2,4,5,6-tetrahydro-4,6,6-trimethyl-2-phenylcyclopentapyrrole-4-carbonitrile 以 乙醇 、 水 为溶剂， 反应 1.0h， 以75%的产率得到2,4,5,6-tetrahydro-1,3-diformyl-4,6,6-trimethyl-2-phenylcyclopentapyrrole-4-carbonitrile
  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

• Cyclopenta[c]pyrrole derivatives
  申请人：Sterling Drug Inc.

  公开号：US04008250A1

  公开（公告）日：1977-02-15

  2,4,5,6-Tetrahydrocyclopenta[c]pyrrole-4-carboxamide and 4-thiocarboxamide derivatives useful as anti-secretory and anti-ulcer agents are prepared by hydrolysis or thiohydrolysis of the corresponding 2,4,5,6-tetrahydrocyclopenta[c]pyrrole-4-carbonitriles or, in the case of the thiocarboxamides, by reaction of the 4-carboxamide with phosphorus pentasulfide.

  2,4,5,6-四氢环戊[c]吡咯-4-羧酰胺和4-硫代羧酰胺衍生物可作为抗分泌和抗溃疡剂，通过对应的2,4,5,6-四氢环戊[c]吡咯-4-碳腈的水解或硫水解或者对于硫代羧酰胺，通过将4-羧酰胺与五硫化磷反应制备。
• 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