5-hydroxy-5-methylhexyl THP ether | 64841-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 5-hydroxy-5-methylhexyl THP ether
• 英文别名: 2-methyl-6-tetrahydropyran-2-yloxy-hexan-2-ol；2-Methyl-6-(oxan-2-yloxy)hexan-2-ol
• CAS: 64841-64-1
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: RGIITKVKXOWYLV-UHFFFAOYSA-N

物化性质

• 沸点：
  315.1±37.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy-5-methylhexyl THP ether 在 N-溴代丁二酰亚胺(NBS) 、 D(+)-10-樟脑磺酸 、 碳酸氢钠 、 三苯基膦 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 41.92h， 生成 N-(4-(4-(Ethyl(5-fluoro-5-methylhexyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide
  参考文献：
  名称：

  Progress toward the Development of a Safe and Effective Agent for Treating Reentrant Cardiac Arrhythmias:  Synthesis and Evaluation of Ibutilide Analogues with Enhanced Metabolic Stability and Diminished Proarrhythmic Potential

  摘要：

  A series of ibutilide analogues with fluorine substituents on the heptyl side chain was prepared and evaluated for class III antiarrhythmic activity, metabolic stability, and proarrhythmic potential. It was found that fluorine substituents stabilized the side chain to metabolic oxidation. Many of the compounds also retained the ability to increase the refractoriness of cardiac tissue at both slow and fast pacing rates. The potential for producing polymorphic ventricular tachycardia in the rabbit model was dependent on the chirality of the benzylic carbon. The S-enantiomers generally had less proarrhythmic activity than the corresponding racemates. One compound from this series (45E, trecetilide fumarate) had excellent antiarrhythmic activity and metabolic stability and was devoid of proarrhythmic activity in the rabbit model. It was chosen for further development.

  DOI：

  10.1021/jm0004289
• 作为产物：
  描述：

  2-(4-氯丁氧基)四氢吡喃 、 丙酮 在 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以29.2%的产率得到5-hydroxy-5-methylhexyl THP ether
  参考文献：
  名称：

  Progress toward the Development of a Safe and Effective Agent for Treating Reentrant Cardiac Arrhythmias:  Synthesis and Evaluation of Ibutilide Analogues with Enhanced Metabolic Stability and Diminished Proarrhythmic Potential

  摘要：

  A series of ibutilide analogues with fluorine substituents on the heptyl side chain was prepared and evaluated for class III antiarrhythmic activity, metabolic stability, and proarrhythmic potential. It was found that fluorine substituents stabilized the side chain to metabolic oxidation. Many of the compounds also retained the ability to increase the refractoriness of cardiac tissue at both slow and fast pacing rates. The potential for producing polymorphic ventricular tachycardia in the rabbit model was dependent on the chirality of the benzylic carbon. The S-enantiomers generally had less proarrhythmic activity than the corresponding racemates. One compound from this series (45E, trecetilide fumarate) had excellent antiarrhythmic activity and metabolic stability and was devoid of proarrhythmic activity in the rabbit model. It was chosen for further development.

  DOI：

  10.1021/jm0004289

文献信息

• Crisan, Annales de Chimie (Cachan, France), 1956, vol. <13>1, p. 436,459
  作者：Crisan

  DOI：——

  日期：——