methyl (2R,3S)-N-1-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carboxylate | 1218811-91-6

• 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: methyl (2R,3S)-N-1-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carboxylate
• CAS: 1218811-91-6
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: YGETYPRTTOIPGJ-SQHWGMCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 、 苯 为溶剂， 以87.1 mg的产率得到methyl (2R,3S)-N-1-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of Trisubstituted Aziridines with N-α-Diazoacyl Camphorsultam

  摘要：

  A Bronsted acid-catalyzed reaction of alpha-substituted alpha-diazocarbonyl compounds bearing camphorsultam as a chiral auxiliary and N-alkoxycarbonyl imines was implemented as an unprecedented means to provide trisubstituted aziridines in a highly stereodefined manner.

  DOI：

  10.1021/ol100104v

文献信息

• Chiral Brønsted Acid-Catalyzed Asymmetric Trisubstituted Aziridine Synthesis Using α-Diazoacyl Oxazolidinones
  作者：Takuya Hashimoto、Hiroki Nakatsu、Kumiko Yamamoto、Keiji Maruoka

  DOI：10.1021/ja203901h

  日期：2011.6.29

  Despite the remarkable advances in catalytic asymmetric aziridinations over the past decades, establishing a general procedure for the stereoselective synthesis of trisubstituted aziridines has remained an elusive goal. Chiral N-triflyl phosphoramide-catalyzed reactions of N-α-diazoacyl oxazolidinones and N-Boc imines were developed as a solution to this unmet challenge.

  尽管在过去几十年中催化不对称氮丙啶化反应取得了显着进展，但建立立体选择性合成三取代氮丙啶的通用程序仍然是一个难以实现的目标。N-α-重氮酰基恶唑烷酮和 N-Boc 亚胺的手性 N-三氟甲基磷酰胺催化反应被开发为解决这一未满足挑战的解决方案。