4-bromo-1-(2,5-dimethylphenyl)butan-1-one | 1226265-11-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-bromo-1-(2,5-dimethylphenyl)butan-1-one
• CAS: 1226265-11-7
• 化学式: C₁₂H₁₅BrO
• 分子量: 255.155
• InChiKey: YZZKORHURORIGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)哌嗪 、 4-bromo-1-(2,5-dimethylphenyl)butan-1-one 在 碳酸氢钠 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以31%的产率得到4-[4-(4-chlorophenyl)piperazin-1-yl]-1-(2,5-dimethylphenyl)butan-1-one
  参考文献：
  名称：

  Bioisosteric Replacement Leading to Biologically Active [2.2]Paracyclophanes with Altered Binding Profiles for Aminergic G-Protein-Coupled Receptors

  摘要：

  Exploring the chemical diversity space of GPCR ligands, we recently discovered [2.2]paracyclophanes as valuable atypical bioisosteres for secondary affinity and selectivity generating moieties. In find out if such an exchange also works for structural moieties that simulate the endogenous neurotransmitter, pi 1 or pi 2 or both systems pi 1 and pi 2 of three representative privileged structures of types 1, 2. and 3 were replaced by a [2.2]paracyclophane unit. Contributions of the respective functionalities to the binding at of a panel of relevant monoaminergic GPCRs were systematically examined. The study led to the paracyclophanylpiperazine 3a displaying excellent D-3 affinity (K-i = 1.6 nM) and a strongly attenuated binding to D-4, 5-HT1 and alpha(1). Whereas functional experiments showed neutral D-3 antagonist properties, mutagenesis studies indicated a binding mode that is similar to its lead compounds of type 3.

  DOI：

  10.1021/jm100899z
• 作为产物：
  描述：

  4-溴丁酰氯 、 对二甲苯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到4-bromo-1-(2,5-dimethylphenyl)butan-1-one
  参考文献：
  名称：

  Bioisosteric Replacement Leading to Biologically Active [2.2]Paracyclophanes with Altered Binding Profiles for Aminergic G-Protein-Coupled Receptors

  摘要：

  Exploring the chemical diversity space of GPCR ligands, we recently discovered [2.2]paracyclophanes as valuable atypical bioisosteres for secondary affinity and selectivity generating moieties. In find out if such an exchange also works for structural moieties that simulate the endogenous neurotransmitter, pi 1 or pi 2 or both systems pi 1 and pi 2 of three representative privileged structures of types 1, 2. and 3 were replaced by a [2.2]paracyclophane unit. Contributions of the respective functionalities to the binding at of a panel of relevant monoaminergic GPCRs were systematically examined. The study led to the paracyclophanylpiperazine 3a displaying excellent D-3 affinity (K-i = 1.6 nM) and a strongly attenuated binding to D-4, 5-HT1 and alpha(1). Whereas functional experiments showed neutral D-3 antagonist properties, mutagenesis studies indicated a binding mode that is similar to its lead compounds of type 3.

  DOI：

  10.1021/jm100899z