3-bromo-5-ethenyl-4,5-dihydro-1,2-oxazole | 206556-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 3-bromo-5-ethenyl-4,5-dihydro-1,2-oxazole
• CAS: 206556-64-1
• 化学式: C₅H₆BrNO
• 分子量: 176.013
• InChiKey: NGUKJOANSJGPKT-UHFFFAOYSA-N

物化性质

• 沸点：
  163.7±43.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-bromo-5-ethenyl-4,5-dihydro-1,2-oxazole 在 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (R)-1-((R)-3-Bromo-4,5-dihydro-isoxazol-5-yl)-2-tert-butylamino-ethanol
  参考文献：
  名称：

  synthesis of new Δ 2 -isoxazoline derivatives and their pharmacological characterization as β-adrenergic receptor antagonists

  摘要：

  A series of Delta(2)-isoxazoline derivatives structurally related to Broxaterol 1 and Falintolol 3 has been prepared and evaluated for their binding affinity to beta(1)- and beta(2)-adrenergic receptors. Among the tested compounds only the 3-isopropenyl anti derivative 4d is as active as the reference compounds. An electron-releasing group, probably operating through a pi-pi interaction, in the 3-position of the isoxazoline nucleus greatly enhances the affinity of the compounds. Conversely, the closest analogs of Broxaterol (3-bromo Delta(2)-isoxazolines 4a and 5a) are at least one order of magnitude less active than the model compound 1. Throughout the series of derivatives the anti stereoisomers are invariably more active than their syn counterparts. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10051-7
• 作为产物：
  描述：

  1,1-二溴甲醛肟 、 1,3-丁二烯 在 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 以82%的产率得到3-bromo-5-ethenyl-4,5-dihydro-1,2-oxazole
  参考文献：
  名称：

  synthesis of new Δ 2 -isoxazoline derivatives and their pharmacological characterization as β-adrenergic receptor antagonists

  摘要：

  A series of Delta(2)-isoxazoline derivatives structurally related to Broxaterol 1 and Falintolol 3 has been prepared and evaluated for their binding affinity to beta(1)- and beta(2)-adrenergic receptors. Among the tested compounds only the 3-isopropenyl anti derivative 4d is as active as the reference compounds. An electron-releasing group, probably operating through a pi-pi interaction, in the 3-position of the isoxazoline nucleus greatly enhances the affinity of the compounds. Conversely, the closest analogs of Broxaterol (3-bromo Delta(2)-isoxazolines 4a and 5a) are at least one order of magnitude less active than the model compound 1. Throughout the series of derivatives the anti stereoisomers are invariably more active than their syn counterparts. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10051-7