3-(3,3-二甲基-2-环氧乙烷基)-2,2-二甲基氮丙啶 | 862884-83-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-(3,3-二甲基-2-环氧乙烷基)-2,2-二甲基氮丙啶
• 英文名称: [1-(3,3-Dimethyl-oxiranyl)-meth-(Z)-ylidene]-isopropyl-amine
• 英文别名: 1-(3,3-dimethyloxiran-2-yl)-N-propan-2-ylmethanimine
• CAS: 862884-83-1
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: WAQGBYJWTAUISW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3,3-二甲基-2-环氧乙烷基)-2,2-二甲基氮丙啶 、 正丁基锂 以 四氢呋喃 为溶剂， 反应 16.0h， 以25%的产率得到2-((2S,3S)-3-Butyl-1-isopropyl-aziridin-2-yl)-propan-2-ol
  参考文献：
  名称：

  Diastereoselective One-Step Synthesis of Functionalized cis-Aziridinyl Alcohols from Oxiranyl Carbaldimines

  摘要：

  Upon treatment with lithiumorganic nucleophiles, trans-configured oxiranyl carbaldimines are transformed into anti-configured cis-aziridinyl alcohols with excellent diastereoselectivity. This conversion may be explained by a new type of the aza-Payne rearrangement, including first a nucleophilic attack on the imine carbon atom with diastereofacial differentiation followed by an intramolecular nucleophilic opening of the oxiranyl ring with simultaneous formation of the aziridine ring.

  DOI：

  10.1021/ol051090l
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 在 molecular sieve 、 双氧水 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 3-(3,3-二甲基-2-环氧乙烷基)-2,2-二甲基氮丙啶
  参考文献：
  名称：

  Diastereoselective One-Step Synthesis of Functionalized cis-Aziridinyl Alcohols from Oxiranyl Carbaldimines

  摘要：

  Upon treatment with lithiumorganic nucleophiles, trans-configured oxiranyl carbaldimines are transformed into anti-configured cis-aziridinyl alcohols with excellent diastereoselectivity. This conversion may be explained by a new type of the aza-Payne rearrangement, including first a nucleophilic attack on the imine carbon atom with diastereofacial differentiation followed by an intramolecular nucleophilic opening of the oxiranyl ring with simultaneous formation of the aziridine ring.

  DOI：

  10.1021/ol051090l

文献信息

• Diastereoselective One-Step Synthesis of Functionalized <i>cis</i>-Aziridinyl Alcohols from Oxiranyl Carbaldimines
  作者：Julia Luzia Bilke、Monika Dzuganova、Roland Fröhlich、Ernst-Ulrich Würthwein

  DOI：10.1021/ol051090l

  日期：2005.7.1

  Upon treatment with lithiumorganic nucleophiles, trans-configured oxiranyl carbaldimines are transformed into anti-configured cis-aziridinyl alcohols with excellent diastereoselectivity. This conversion may be explained by a new type of the aza-Payne rearrangement, including first a nucleophilic attack on the imine carbon atom with diastereofacial differentiation followed by an intramolecular nucleophilic opening of the oxiranyl ring with simultaneous formation of the aziridine ring.