5-Ethenyl-3-(3-methoxyphenyl)-4,5-dihydro-1,2-oxazole | 161064-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-Ethenyl-3-(3-methoxyphenyl)-4,5-dihydro-1,2-oxazole
• CAS: 161064-06-8
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: WKCKPKZCKBMBJI-UHFFFAOYSA-N

物化性质

• 沸点：
  299.977±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.100±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Ethenyl-3-(3-methoxyphenyl)-4,5-dihydro-1,2-oxazole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以36%的产率得到
  参考文献：
  名称：

  Conformationally restrained β-blocking oxime ethers. 2. Synthesis and β-adrenergic properties of diastereoisomeric anti and syn 2-(5′-(3′-aryl-substituted)isoxazolidinyl)-N-alkylethanolamines☆

  摘要：

  The diastereoisomeric 2-(5'-(3'-aryl)isoxazolidinyl) ethanolamines 1c-h-4c-h were synthesized as analogs of the corresponding P-blocking isoxazolines unsubstituted on the aromatic ring 1a-4a, with the aim of checking the effects on the adrenergic properties of the insertion of a methoxy group or a chlorine atom in the ortho, meta or para position of the phenyl ring of 1a-4a. The relative configurations of 1c-h-4c-h were assigned on the basis of their H-1-NMR spectral characteristics. The new isoxazolines 1c-h-4c-h were tested for their affinity towards beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments; compounds showing the highest affinity were also assayed for their beta-adrenergic activity by functional tests on isolated preparations. The results showed that most of the new compounds (1c-h-4c-h) possess a slightly better capacity to interact with the beta-receptors, compared with the corresponding analogs unsubstituted on the phenyl ring (1a-4a), and that the substitution that leads to compounds with the best properties is the one with the chlorine atom. Quantum mechanical calculations carried out in order to look for possible correlations between the beta-adrenergic properties and the conformational and electronic characteristics induced by the presence of the substituents on the phenyl ring of compounds of types 1-4 do not suggest any reasonable explanation for the trend of the affinity data.

  DOI：

  10.1016/0223-5234(94)90108-2
• 作为产物：
  描述：

  (E)-3-methoxybenzaldoxime 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-Ethenyl-3-(3-methoxyphenyl)-4,5-dihydro-1,2-oxazole
  参考文献：
  名称：

  Conformationally restrained β-blocking oxime ethers. 2. Synthesis and β-adrenergic properties of diastereoisomeric anti and syn 2-(5′-(3′-aryl-substituted)isoxazolidinyl)-N-alkylethanolamines☆

  摘要：

  The diastereoisomeric 2-(5'-(3'-aryl)isoxazolidinyl) ethanolamines 1c-h-4c-h were synthesized as analogs of the corresponding P-blocking isoxazolines unsubstituted on the aromatic ring 1a-4a, with the aim of checking the effects on the adrenergic properties of the insertion of a methoxy group or a chlorine atom in the ortho, meta or para position of the phenyl ring of 1a-4a. The relative configurations of 1c-h-4c-h were assigned on the basis of their H-1-NMR spectral characteristics. The new isoxazolines 1c-h-4c-h were tested for their affinity towards beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments; compounds showing the highest affinity were also assayed for their beta-adrenergic activity by functional tests on isolated preparations. The results showed that most of the new compounds (1c-h-4c-h) possess a slightly better capacity to interact with the beta-receptors, compared with the corresponding analogs unsubstituted on the phenyl ring (1a-4a), and that the substitution that leads to compounds with the best properties is the one with the chlorine atom. Quantum mechanical calculations carried out in order to look for possible correlations between the beta-adrenergic properties and the conformational and electronic characteristics induced by the presence of the substituents on the phenyl ring of compounds of types 1-4 do not suggest any reasonable explanation for the trend of the affinity data.

  DOI：

  10.1016/0223-5234(94)90108-2

文献信息

• Anionic Domino C<i>-</i>O-Heterocyclization Approach for the Synthesis of 5-Vinyl Isoxazolines
  作者：H. Kumar、Naveed Qazi、Parvinder Singh、Sumira Jan

  DOI：10.1055/s-2007-980346

  日期：2007.6

  5-Vinyl isoxazolines were isolated in high yields through domino nucleophilic addition-anionic C-O-heterocyclization, when allyl organometallics derived from trans-1,4-dihalobutene were reacted with nitrile oxides.

  通过多米诺亲核加成-阴离子C-O杂环化反应，以高产率分离得到了5-乙烯基异恶唑啉，该反应是在将来自反式-1,4-二卤代丁烯的烯丙基有机金属化合物与腈氧化物反应时进行的。
• Conformationally restrained β-blocking oxime ethers. 2. Synthesis and β-adrenergic properties of diastereoisomeric anti and syn 2-(5′-(3′-aryl-substituted)isoxazolidinyl)-N-alkylethanolamines☆
  作者：A BALSAMO、M BRESCHI、G CHIELLINI、A LUCACCHINI、M MACCHIA、A MARTINELLI、C MARTINI、C NARDINI、E ORLANDINI、F ROMAGNOLI

  DOI：10.1016/0223-5234(94)90108-2

  日期：——

  The diastereoisomeric 2-(5'-(3'-aryl)isoxazolidinyl) ethanolamines 1c-h-4c-h were synthesized as analogs of the corresponding P-blocking isoxazolines unsubstituted on the aromatic ring 1a-4a, with the aim of checking the effects on the adrenergic properties of the insertion of a methoxy group or a chlorine atom in the ortho, meta or para position of the phenyl ring of 1a-4a. The relative configurations of 1c-h-4c-h were assigned on the basis of their H-1-NMR spectral characteristics. The new isoxazolines 1c-h-4c-h were tested for their affinity towards beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments; compounds showing the highest affinity were also assayed for their beta-adrenergic activity by functional tests on isolated preparations. The results showed that most of the new compounds (1c-h-4c-h) possess a slightly better capacity to interact with the beta-receptors, compared with the corresponding analogs unsubstituted on the phenyl ring (1a-4a), and that the substitution that leads to compounds with the best properties is the one with the chlorine atom. Quantum mechanical calculations carried out in order to look for possible correlations between the beta-adrenergic properties and the conformational and electronic characteristics induced by the presence of the substituents on the phenyl ring of compounds of types 1-4 do not suggest any reasonable explanation for the trend of the affinity data.