3-(2-tert-butoxycarbonylamino-1-oxo-3-phenylpropyl)-1,3-oxazolidin-2-one | 145889-50-5

• 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: 3-(2-tert-butoxycarbonylamino-1-oxo-3-phenylpropyl)-1,3-oxazolidin-2-one
• 英文别名: tert-butyl N-[1-oxo-1-(2-oxo-1,3-oxazolidin-3-yl)-3-phenylpropan-2-yl]carbamate
• CAS: 145889-50-5
• 化学式: C₁₇H₂₂N₂O₅
• 分子量: 334.372
• InChiKey: YUTUJFARZYALNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  溴乙酸乙酯 、 3-(2-tert-butoxycarbonylamino-1-oxo-3-phenylpropyl)-1,3-oxazolidin-2-one 在 锌 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到ethyl-4-(carboxamino)-5-phenyl-3-oxopentanoate 4-tert-butyl ester
  参考文献：
  名称：

  Synthesis of .beta.-keto esters by the Reformatsky reaction of 3-acyloxazolidin-2-ones and -thiazolidine-2-thiones

  摘要：

  DOI：

  10.1021/jo00055a046
• 作为产物：
  描述：

  N-BOC-脒三苯基膦 在 Oxone 、 potassium carbonate 作用下， 以 四氢呋喃 、 氯仿 、 水 、 甲苯 为溶剂， 反应 17.5h， 生成 3-(2-tert-butoxycarbonylamino-1-oxo-3-phenylpropyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Electrophilic amination: preparation and use of N-Boc-3-(4-cyanophenyl)oxaziridine, a new reagent that transfers a N-Boc group to N- and C-nucleophiles

  摘要：

  We describe the preparation of the title compound 2b via aza-Wittig reaction of N-Boc-triphenyliminophosphorane (6) with 4-cyanobenzaldehyde followed by Oxone oxidation of the resulting imine 5b. Oxaziridine 2b is a stable, crystalline solid, which transfers under mild conditions its N-Boc fragment to primary and secondary amines (to give N(beta)-Boc-hydrazines) and enolates (to give N-Boc-amino derivatives).

  DOI：

  10.1021/jo00070a007

文献信息

• Electrophilic amination: preparation and use of N-Boc-3-(4-cyanophenyl)oxaziridine, a new reagent that transfers a N-Boc group to N- and C-nucleophiles
  作者：Joelle Vidal、Laure Guy、Sebastien Sterin、Andre Collet

  DOI：10.1021/jo00070a007

  日期：1993.8

  We describe the preparation of the title compound 2b via aza-Wittig reaction of N-Boc-triphenyliminophosphorane (6) with 4-cyanobenzaldehyde followed by Oxone oxidation of the resulting imine 5b. Oxaziridine 2b is a stable, crystalline solid, which transfers under mild conditions its N-Boc fragment to primary and secondary amines (to give N(beta)-Boc-hydrazines) and enolates (to give N-Boc-amino derivatives).
• 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.
• Synthesis of .beta.-keto esters by the Reformatsky reaction of 3-acyloxazolidin-2-ones and -thiazolidine-2-thiones
  作者：Choji Kashima、Xin Cheng Huang、Yukari Harada、Akira Hosomi

  DOI：10.1021/jo00055a046

  日期：1993.1