(+/-)-3-azido-2-(4-fluorophenyl)-2-methylpropan-1-ol | 1016972-91-0

• 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: (+/-)-3-azido-2-(4-fluorophenyl)-2-methylpropan-1-ol
• CAS: 1016972-91-0
• 化学式: C₁₀H₁₂FN₃O
• 分子量: 209.223
• InChiKey: DESGLOJSTQXBMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.99
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-3-azido-2-(4-fluorophenyl)-2-methylpropan-1-ol 、 4-叔丁基环己酮 在 三氟化硼乙醚 、 氢氧化钾 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 5-tert-butyl-1-(2-(4-fluorophenyl)-3-hydroxy-2-methylpropyl)azepan-2-one 、 5-tert-butyl-1-(2-(4-fluorophenyl)-3-hydroxy-2-methylpropyl)azepan-2-one
  参考文献：
  名称：

  叠氮化物介导的不对称环膨胀反应中的非键，有吸引力的阳离子-π相互作用

  摘要：

  The influence of attractive, nonbonded interactions on the reactions of 1,2- and 1,3-hydroxyalkyl azides with ketones has been investigated through experimental and computational means. A series of 1,3-hydroxyalkyl azides bearing electronically tuned aromatic groups at the 2 position were prepared and reacted along with several derivatives designed to conformationally restrict the rotational orientation of the aromatic substituent. These studies showed that a cation-pi interaction between an aryl moiety and an N-2(+) leaving group plays a role in determining the stereoselectivity of these reactions. A series of ab initio calculations supported this hypothesis. A computational and experimental analysis suggested a primarily steric model for the analogous reactions of substituted 2-azido-1-ethanol analogues.

  DOI：

  10.1021/jo800222r
• 作为产物：
  描述：

  (+/-)-2-(4-fluorophenyl)-2-methylpropane-1,3-diol 在 迭氮酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 18.0h， 以77%的产率得到(+/-)-3-azido-2-(4-fluorophenyl)-2-methylpropan-1-ol
  参考文献：
  名称：

  叠氮化物介导的不对称环膨胀反应中的非键，有吸引力的阳离子-π相互作用

  摘要：

  The influence of attractive, nonbonded interactions on the reactions of 1,2- and 1,3-hydroxyalkyl azides with ketones has been investigated through experimental and computational means. A series of 1,3-hydroxyalkyl azides bearing electronically tuned aromatic groups at the 2 position were prepared and reacted along with several derivatives designed to conformationally restrict the rotational orientation of the aromatic substituent. These studies showed that a cation-pi interaction between an aryl moiety and an N-2(+) leaving group plays a role in determining the stereoselectivity of these reactions. A series of ab initio calculations supported this hypothesis. A computational and experimental analysis suggested a primarily steric model for the analogous reactions of substituted 2-azido-1-ethanol analogues.

  DOI：

  10.1021/jo800222r