(E/Z)-2-(2,4-dichlorobenzoyl)-3,5,5,-trimethylhex-2-enenitrile | 1529778-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E/Z)-2-(2,4-dichlorobenzoyl)-3,5,5,-trimethylhex-2-enenitrile
• CAS: 1529778-16-2
• 化学式: C₁₆H₁₇Cl₂NO
• 分子量: 310.223
• InChiKey: VVPRQNWYAPOXMD-UHFFFAOYSA-N

物化性质

• 沸点：
  435.7±45.0 °C(predicted)
• 密度：
  1.177±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E/Z)-2-(2,4-dichlorobenzoyl)-3,5,5,-trimethylhex-2-enenitrile 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 乙醇 、 溶剂黄146 、 乙腈 为溶剂， 反应 10.0h， 生成 2-[5-bromo-3-(2,4-dichlorobenzoyl)-4-(2,2-dimethylpropyl)thiophen-2-yl]isoindol-ine-1,3-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-amino-3-aroyl-4-neopentyl-5-substituted thiophene derivatives as allosteric enhancers of the A1 adenosine receptor

  摘要：

  2-Amino-3-benzoyl thiophenes have been widely reported to act as allosteric enhancers at the A(1) adenosine receptor. Their activity can be increased considerably by appropriate substitutions at the 4- and 5-positions of the thiophene ring. Substituent size at the thiophene C-4 position seemed to be a factor closely related to activity, with the 4-neopentyl (2,2-dimethylpropyl) substitution showing the greatest enhanced activity. A wide series of 2-amino-3-aroyl-4-neopentylthiophene derivatives with general structure 3, characterized by the presence of different substituents (bromine, aryl and heteroaryl) at the 5-position of the thiophene ring, have been identified as potent AEs at the A(1)AR. With only one exception, all of the synthesized compounds proved to be superior to the reference compound PD 81,723 in a functional assay. Derivatives 3p, 3u, 3am, 3ap and 3ar were the most active compounds in binding (saturation and competition) and functional cAMP studies, being able to potentiate agonist [H-3]CCPA binding to the A(1) receptor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.043
• 作为产物：
  描述：

  4,4-二甲基-2-戊酮 、 2,4-二氯苯甲腈 在 溶剂黄146 、 β-丙氨酸 作用下， 以 苯 为溶剂， 反应 34.0h， 以78%的产率得到(E/Z)-2-(2,4-dichlorobenzoyl)-3,5,5,-trimethylhex-2-enenitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-amino-3-aroyl-4-neopentyl-5-substituted thiophene derivatives as allosteric enhancers of the A1 adenosine receptor

  摘要：

  2-Amino-3-benzoyl thiophenes have been widely reported to act as allosteric enhancers at the A(1) adenosine receptor. Their activity can be increased considerably by appropriate substitutions at the 4- and 5-positions of the thiophene ring. Substituent size at the thiophene C-4 position seemed to be a factor closely related to activity, with the 4-neopentyl (2,2-dimethylpropyl) substitution showing the greatest enhanced activity. A wide series of 2-amino-3-aroyl-4-neopentylthiophene derivatives with general structure 3, characterized by the presence of different substituents (bromine, aryl and heteroaryl) at the 5-position of the thiophene ring, have been identified as potent AEs at the A(1)AR. With only one exception, all of the synthesized compounds proved to be superior to the reference compound PD 81,723 in a functional assay. Derivatives 3p, 3u, 3am, 3ap and 3ar were the most active compounds in binding (saturation and competition) and functional cAMP studies, being able to potentiate agonist [H-3]CCPA binding to the A(1) receptor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.043