1-(2-aminoethyl)-3,3-dimethyldiaziridine | 139223-40-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(2-aminoethyl)-3,3-dimethyldiaziridine
• 英文别名: 1-(beta-Aminoethyl)-3,3-dimethyldiaziridine；2-(3,3-dimethyldiaziridin-1-yl)ethanamine
• CAS: 139223-40-8
• 化学式: C₅H₁₃N₃
• 分子量: 115.178
• InChiKey: IYBXIOOBEZAWRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetoxime tosylate 、 1-(2-aminoethyl)-3,3-dimethyldiaziridine 在 二乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 170.0h， 以46.5%的产率得到3,3-dimethyl-1-[2-(3,3-dimethyldiaziridin-1-yl)ethyl]diaziridine
  参考文献：
  名称：

  Synthesis and structure of 1-[ω-(3,3-dialkyldiaziridin-1-yl)alkyl]-3,3-dialkyldiaziridines

  摘要：

  建立了一种基于酮肟邻芳烃磺酸盐与亚烷基二胺反应合成1-[ω-(3,3-二烷基二氮丙啶-1-基)烷基]-3,3-二烷基二氮丙啶的方法。分离出1-[2-(3,3-二甲基二氮丙啶-1-基)乙基]-3,3-二甲基二氮丙啶的非对映异构体（外消旋和内消旋形式）。通过X射线衍射分析证实了内消旋形式的结构。

  DOI：

  10.1007/s11172-007-0241-7
• 作为产物：
  描述：

  N-[2-(3,3-Dimethyl-diaziridin-1-yl)-ethyl]-acetamide 在 氢氧化钾 作用下， 以69%的产率得到1-(2-aminoethyl)-3,3-dimethyldiaziridine
  参考文献：
  名称：

  The role of pH in the synthesis of diaziridines

  摘要：

  The greatest yield in the synthesis of diaziridines from carbonyl compounds, amines, and aminating reagents in water is achieved at a specific pH, which shifts to less alkaline values with increasing -I effect of the substituents in the carbonyl compound and with decreasing pK(BH+) value of the amine. The role of pH is related to the conditions for the generation of an immonium from the intermediate alpha-aminocarbinol. The nuclear Overhauser effect was used to determine the orientation of the substituents in several diastereomers of the didikyldiaziridines obtained.

  DOI：

  10.1007/bf00959732

文献信息

• The role of pH in the synthesis of diaziridines
  作者：V. V. Kuznetsov、N. N. Makhova、Yu. A. Strelenko、L. I. Khmel'nitskii

  DOI：10.1007/bf00959732

  日期：1991.12

  The greatest yield in the synthesis of diaziridines from carbonyl compounds, amines, and aminating reagents in water is achieved at a specific pH, which shifts to less alkaline values with increasing -I effect of the substituents in the carbonyl compound and with decreasing pK(BH+) value of the amine. The role of pH is related to the conditions for the generation of an immonium from the intermediate alpha-aminocarbinol. The nuclear Overhauser effect was used to determine the orientation of the substituents in several diastereomers of the didikyldiaziridines obtained.
• Synthesis and structure of 1-[ω-(3,3-dialkyldiaziridin-1-yl)alkyl]-3,3-dialkyldiaziridines
  作者：V. Yu. Petukhova、Yu. A. Strelenko、K. A. Lyssenko、N. N. Makhova

  DOI：10.1007/s11172-007-0241-7

  日期：2007.8

  A method for the synthesis of 1-[ω-(3,3-dialkyldiaziridin-1-yl)alkyl]-3,3-dialkyldiaziridines based on the reaction of ketoxime O-arenesulfonates with alkylenediamines was developed. Diastrereomers (the racemic and meso forms) of 1-[2-(3,3-dimethyldiaziridin-1-yl)ethyl]-3,3-dimethyldiaziridine were isolated. The structure of the meso form was confirmed by X-ray diffraction analysis.

  建立了一种基于酮肟邻芳烃磺酸盐与亚烷基二胺反应合成1-[ω-(3,3-二烷基二氮丙啶-1-基)烷基]-3,3-二烷基二氮丙啶的方法。分离出1-[2-(3,3-二甲基二氮丙啶-1-基)乙基]-3,3-二甲基二氮丙啶的非对映异构体（外消旋和内消旋形式）。通过X射线衍射分析证实了内消旋形式的结构。