N-(methoxycarbonylamino)morpholine | 134920-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: N-(methoxycarbonylamino)morpholine
• 英文别名: methyl N-morpholin-4-ylcarbamate
• CAS: 134920-20-0
• 化学式: C₆H₁₂N₂O₃
• 分子量: 160.173
• InChiKey: NWHMRHSUJBVTGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吗啉 、 甲基3-苯基-2-氧杂氮丙啶羧酸酯 以 乙醚 为溶剂， 反应 0.5h， 以91%的产率得到N-(methoxycarbonylamino)morpholine
  参考文献：
  名称：

  N-amination using N-methoxycarbonyl-3-phenyloxaziridine. Direct access to chiral N_β-protected α-hydrazinoacids and carbazates

  摘要：

  初级和次级胺的 N–H，包括 α-氨基酸，可以在温和条件下与 N-甲氧基碳酰基-3-苯基呋喃啶 1 反应，转化为相应的脲体 N–NH–CO2Me。

  DOI：

  10.1039/c39910000435

文献信息

• N-amination using N-methoxycarbonyl-3-phenyloxaziridine. Direct access to chiral N_β-protected α-hydrazinoacids and carbazates
  作者：Joëlle Vidal、Jacques Drouin、André Collet

  DOI：10.1039/c39910000435

  日期：——

  Primary and secondary amines N–H, including α-aminoacids, can be converted under mild conditions to the corresponding carbazates N–NH–CO2Me, on reaction with N-methoxycarbonyl-3-phenyloxaziridine 1.

  初级和次级胺的 N–H，包括 α-氨基酸，可以在温和条件下与 N-甲氧基碳酰基-3-苯基呋喃啶 1 反应，转化为相应的脲体 N–NH–CO2Me。
• N-Alkyloxycarbonyl-3-aryloxaziridines: Their Preparation, Structure, and Utilization As Electrophilic Amination Reagents
  作者：Joëlle Vidal、Stéphanie Damestoy、Laure Guy、Jean-Christophe Hannachi、André Aubry、Andreé Collet、André Aubry

  DOI：10.1002/chem.19970031019

  日期：1997.10

  AbstractThis paper reports the synthesis of a series of N‐protected oxaziridines (N‐Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N‐alkoxycar‐bonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N‐protected fragment to primary and secondary amines to give protected hydrazines in fair to excellent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N‐protected α‐hydrazino acids. Enolates are C‐aminated to give N‐protected α‐amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.