1,3-bis(chloromethyl)-2,4,5,6-tetrahydro-4,6,6-trimethyl-2-phenylcyclopentapyrrole-4-carbonitrile | 61271-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1,3-bis(chloromethyl)-2,4,5,6-tetrahydro-4,6,6-trimethyl-2-phenylcyclopentapyrrole-4-carbonitrile
• 英文别名: 1,3-bis(chloromethyl)-4,6,6-trimethyl-2-phenyl-5H-cyclopenta[c]pyrrole-4-carbonitrile
• CAS: 61271-31-6
• 化学式: C₁₉H₂₀Cl₂N₂
• 分子量: 347.287
• InChiKey: AAJVGVGNTMZJGC-UHFFFAOYSA-N

物化性质

• 熔点：
  126-128.5 °C
• 沸点：
  466.3±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-bis(chloromethyl)-2,4,5,6-tetrahydro-4,6,6-trimethyl-2-phenylcyclopentapyrrole-4-carbonitrile 在 palladium on activated charcoal 、 硫酸 、 三氟乙酸 作用下， 以 various solvent(s) 为溶剂， 反应 11.0h， 生成 2,4,5,6-tetrahydro-3,4,6,6-tetramethyl-2-phenylcyclopentapyrrole-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：

  1,3,4,6,6-pentamethyl-2-phenyl-2,4,5,6-tetrahydro-cyclopenta[c]pyrrole-4-carbonitrile 在 磺酰氯 作用下， 以 四氯化碳 为溶剂， 以72%的产率得到1,3-bis(chloromethyl)-2,4,5,6-tetrahydro-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

• 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
• US4239687A
  申请人：——

  公开号：US4239687A

  公开（公告）日：1980-12-16
• US4273713A
  申请人：——

  公开号：US4273713A

  公开（公告）日：1981-06-16