4-(benzoyloxy)-1-phenylbutylamine | 1407999-65-8

• 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: 4-(benzoyloxy)-1-phenylbutylamine
• 英文别名: (4-Amino-4-phenylbutyl) benzoate；(4-amino-4-phenylbutyl) benzoate
• CAS: 1407999-65-8
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: NBZWIZSSNBIAFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-phenylbutyl benzoate 在 N-羟基邻苯二甲酰亚胺 、 溶剂黄146 、 锌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 生成 4-(benzoyloxy)-1-phenylbutylamine
  参考文献：
  名称：

  Radical Amination of C(sp³)–H Bonds Using N-Hydroxyphthalimide and Dialkyl Azodicarboxylate

  摘要：

  A direct conversion of C(sp(3))-H bonds to C(sp3)-N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl azodicarboxylate. NHPI functions as a precursor of the electron-deficient phthalimide N-oxyl radical (PINO) to abstract hydrogens, and dialkyl azodicarboxylate acts as a trapping agent of the resultant carbon radical to generate the hydrazine derivatives. This C-H amination proceeds in a highly chemoselective manner with a wide applicability to functionalize benzylic, propargylic, and aliphatic C-H bonds. Furthermore, the obtained hydrazine compounds were readily converted to the corresponding carbamates or amines. Hence, the present protocol for direct introduction of the nitrogen functionality serves as a powerful tool for efficient construction of nitrogen-substituted natural products and pharmaceuticals.

  DOI：

  10.1021/jo301840e

文献信息

• Radical Amination of C(sp³)–H Bonds Using <i>N</i>-Hydroxyphthalimide and Dialkyl Azodicarboxylate
  作者：Yuuki Amaoka、Shin Kamijo、Tamaki Hoshikawa、Masayuki Inoue

  DOI：10.1021/jo301840e

  日期：2012.11.16

  A direct conversion of C(sp(3))-H bonds to C(sp3)-N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl azodicarboxylate. NHPI functions as a precursor of the electron-deficient phthalimide N-oxyl radical (PINO) to abstract hydrogens, and dialkyl azodicarboxylate acts as a trapping agent of the resultant carbon radical to generate the hydrazine derivatives. This C-H amination proceeds in a highly chemoselective manner with a wide applicability to functionalize benzylic, propargylic, and aliphatic C-H bonds. Furthermore, the obtained hydrazine compounds were readily converted to the corresponding carbamates or amines. Hence, the present protocol for direct introduction of the nitrogen functionality serves as a powerful tool for efficient construction of nitrogen-substituted natural products and pharmaceuticals.