(2R,3S)-2-ethyl 3-methyl 1-((R)-1-phenylethyl)aziridine-2,3-dicarboxylate | 1277179-79-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3S)-2-ethyl 3-methyl 1-((R)-1-phenylethyl)aziridine-2,3-dicarboxylate
• 英文别名: 2-O-ethyl 3-O-methyl (2R,3S)-1-[(1R)-1-phenylethyl]aziridine-2,3-dicarboxylate
• CAS: 1277179-79-9
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: YDHDAWOWFHJPJI-JONSLCSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  [(R)-1-叠氮乙基]苯 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 (2R,3S)-2-ethyl 3-methyl 1-((R)-1-phenylethyl)aziridine-2,3-dicarboxylate
  参考文献：
  名称：

  Origins of Selectivity in Brønsted Acid-Promoted Diazoalkane−Azomethine Reactions (The Aza-Darzens Aziridine Synthesis)

  摘要：

  The mechanism of the Bronsted acid-catalyzed aza-Darzens reaction is explored by charting the stereochemical outcome of the triflic acid-promoted conversion of trans-triazolines to cis-aziridines. These experiments are consistent with the intermediacy of an alpha-diazonium-beta-amino ester intermediate.

  DOI：

  10.1021/ol200313m

文献信息

• Origins of Selectivity in Brønsted Acid-Promoted Diazoalkane−Azomethine Reactions (The Aza-Darzens Aziridine Synthesis)
  作者：Timothy L. Troyer、Hubert Muchalski、Ki Bum Hong、Jeffrey N. Johnston

  DOI：10.1021/ol200313m

  日期：2011.4.1

  The mechanism of the Bronsted acid-catalyzed aza-Darzens reaction is explored by charting the stereochemical outcome of the triflic acid-promoted conversion of trans-triazolines to cis-aziridines. These experiments are consistent with the intermediacy of an alpha-diazonium-beta-amino ester intermediate.