2-imino-3-phenyltetrahydrofuran | 153276-29-0

• 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: 2-imino-3-phenyltetrahydrofuran
• 英文别名: 3-Phenyloxolan-2-imine
• CAS: 153276-29-0
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: HFBRBVSEFYCION-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-imino-3-phenyltetrahydrofuran 在 盐酸 作用下， 反应 2.0h， 以88%的产率得到4,5-二氢-3-苯基-2-呋喃酮
  参考文献：
  名称：

  Mechanism of the formation in vivo of α-phenyl-γ-lactones in the glutethimide series

  摘要：

  The isolation of gamma-lactones from the urines of humans or animals treated with glutethimide or aminoglutethimide required an explanation. The question was studied on the glutethimide model. Potential metabolites such as beta-hydroxymetabolite, gamma-lactone amide, and gamma-lactone acid were synthesized. Glutethimide was first administered to rats at high and normal doses. The corresponding gamma-lactone amide, resulting from alcoholysis of beta-hydroxyglutethimide, was also administered to rats. The amounts of the various gamma-lactone derivatives isolated from the urine were discussed and it was concluded that the alpha-phenyl-gamma-lactone was formed in vivo via beta-hydroxylation of glutethimide followed by intramolecular alcoholysis. The lactone amide was then oxidized and dealkylated via an intramolecular mechanism leading to the corresponding alpha-phenyl-gamma-lactone.

  DOI：

  10.1016/0223-5234(93)90090-2
• 作为产物：
  描述：

  4-(2-tetrahydropyranyloxyethyl)-2-phenylbutanenitrile 160.0 ℃ 、1.71 kPa 条件下， 以30%的产率得到2-imino-3-phenyltetrahydrofuran
  参考文献：
  名称：

  Mechanism of the formation in vivo of α-phenyl-γ-lactones in the glutethimide series

  摘要：

  The isolation of gamma-lactones from the urines of humans or animals treated with glutethimide or aminoglutethimide required an explanation. The question was studied on the glutethimide model. Potential metabolites such as beta-hydroxymetabolite, gamma-lactone amide, and gamma-lactone acid were synthesized. Glutethimide was first administered to rats at high and normal doses. The corresponding gamma-lactone amide, resulting from alcoholysis of beta-hydroxyglutethimide, was also administered to rats. The amounts of the various gamma-lactone derivatives isolated from the urine were discussed and it was concluded that the alpha-phenyl-gamma-lactone was formed in vivo via beta-hydroxylation of glutethimide followed by intramolecular alcoholysis. The lactone amide was then oxidized and dealkylated via an intramolecular mechanism leading to the corresponding alpha-phenyl-gamma-lactone.

  DOI：

  10.1016/0223-5234(93)90090-2

文献信息

• Mechanism of the formation in vivo of α-phenyl-γ-lactones in the glutethimide series
  作者：Y Al-Tarakji-Khalfh、C Cavé、S Ménager、Y Legras、C Combet Farnoux、O Lafont

  DOI：10.1016/0223-5234(93)90090-2

  日期：1993.1

  The isolation of gamma-lactones from the urines of humans or animals treated with glutethimide or aminoglutethimide required an explanation. The question was studied on the glutethimide model. Potential metabolites such as beta-hydroxymetabolite, gamma-lactone amide, and gamma-lactone acid were synthesized. Glutethimide was first administered to rats at high and normal doses. The corresponding gamma-lactone amide, resulting from alcoholysis of beta-hydroxyglutethimide, was also administered to rats. The amounts of the various gamma-lactone derivatives isolated from the urine were discussed and it was concluded that the alpha-phenyl-gamma-lactone was formed in vivo via beta-hydroxylation of glutethimide followed by intramolecular alcoholysis. The lactone amide was then oxidized and dealkylated via an intramolecular mechanism leading to the corresponding alpha-phenyl-gamma-lactone.