Methyl 5-[ethoxycarbonyl-(ethoxycarbonylamino)amino]-5-phenylpentanoate | 1407999-27-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 5-[ethoxycarbonyl-(ethoxycarbonylamino)amino]-5-phenylpentanoate
• 英文别名: methyl 5-[ethoxycarbonyl-(ethoxycarbonylamino)amino]-5-phenylpentanoate
• CAS: 1407999-27-2
• 化学式: C₁₈H₂₆N₂O₆
• 分子量: 366.414
• InChiKey: JKLGRVJPSAHIQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-苯基-正戊酸甲酯 、 偶氮二甲酸二乙酯 在 N-羟基邻苯二甲酰亚胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以93%的产率得到Methyl 5-[ethoxycarbonyl-(ethoxycarbonylamino)amino]-5-phenylpentanoate
  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.