Bis(2,2,2-trichloroethyl) 1-cyclododecylhydrazine-1,2-dicarboxylate | 1407999-64-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: Bis(2,2,2-trichloroethyl) 1-cyclododecylhydrazine-1,2-dicarboxylate
• 英文别名: 2,2,2-trichloroethyl N-cyclododecyl-N-(2,2,2-trichloroethoxycarbonylamino)carbamate
• CAS: 1407999-64-7
• 化学式: C₁₈H₂₈Cl₆N₂O₄
• 分子量: 549.149
• InChiKey: BPXBODQVURAUFE-UHFFFAOYSA-N

物化性质

• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Bis(2,2,2-trichloroethyl) 1-cyclododecylhydrazine-1,2-dicarboxylate 在 溶剂黄146 、 锌 作用下， 以 丙酮 为溶剂， 以89%的产率得到环十二胺
  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
• 作为产物：
  描述：

  环十二烷 、 偶氮基二羧酸双(2,2,2-三氯乙酯) 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 5.0h， 以87%的产率得到Bis(2,2,2-trichloroethyl) 1-cyclododecylhydrazine-1,2-dicarboxylate
  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.