N-benzyloxycarbonyl(Cbz)-3-phenyloxaziridine | 153942-10-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyloxycarbonyl(Cbz)-3-phenyloxaziridine
• 英文别名: N-benzyloxycarbonyl-3-phenyloxaziridine；N-CBZ-3-phenyl-oxaziridine；benzyl 3-phenyloxaziridine-2-carboxylate
• CAS: 153942-10-0
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: BFIPLSFNLSVRDV-UHFFFAOYSA-N

物化性质

• 沸点：
  364.2±52.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tetramethylammonium salt of L-phenylalanine 、 N-benzyloxycarbonyl(Cbz)-3-phenyloxaziridine 以 二氯甲烷 为溶剂， 以76%的产率得到(S)-2-(2-((benzyloxy)carbonyl)hydrazinyl)-3-phenylpropanoic acid
  参考文献：
  名称：

  Amination with N-benzyloxycarbonyl-3-phenyloxaziridine as a route to sensitive chiral α-hydrazino acids: Synthesis of l-hydrazino serine

  摘要：

  N-Cbz-3-phenyloxaziridine can be generated in a two step process. This is a new reagent for direct electrophilic N-amination of chiral alpha-amino acids and their derivatives which affords the corresponding hydrazino acids protected with a readily removable N-Cbz group. Application of this methodology to a facile synthesis of L-hydrazino serine, a potentially useful biological tool, is described

  DOI：

  10.1016/s0040-4039(00)91814-8
• 作为产物：
  描述：

  N-benzylidene-1,1,1-trimethylsilanamine 在 LiMCPBA 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 4.0h， 生成 N-benzyloxycarbonyl(Cbz)-3-phenyloxaziridine
  参考文献：
  名称：

  N-Alkyloxycarbonyl-3-aryloxaziridines: Their Preparation, Structure, and Utilization As Electrophilic Amination Reagents

  摘要：

  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.

  DOI：

  10.1002/chem.19970031019

文献信息

• Antipicornaviral compounds and methods for their use and preparation
  申请人：Agouron Pharmaceuticals, Inc.

  公开号：US05962487A1

  公开（公告）日：1999-10-05

  Picornaviral 3C protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of picornaviral 3C proteases. These compounds, as well as pharmaceutical compositions that contain these compounds, are suitable for treating patients or hosts infected with one or more picornaviruses. Several novel methods and intermediates can be used to prepare the novel picornaviral 3C protease inhibitors of the present invention.

  Picornaviral 3C蛋白酶抑制剂，可通过化学合成获得，能够抑制或阻断picornaviral 3C蛋白酶的生物活性。这些化合物以及含有这些化合物的制药组合物，适用于治疗感染一种或多种picornaviruses的患者或宿主。本发明还可以使用几种新颖的方法和中间体来制备这些新颖的picornaviral 3C蛋白酶抑制剂。
• ANTIPICORNAVIRAL COMPOUNDS AND METHODS FOR THEIR USE AND PREPARATION
  申请人：AGOURON PHARMACEUTICALS, INC.

  公开号：EP1037905A1

  公开（公告）日：2000-09-27
• US5962487A
  申请人：——

  公开号：US5962487A

  公开（公告）日：1999-10-05
• [EN] ANTIPICORNAVIRAL COMPOUNDS AND METHODS FOR THEIR USE AND PREPARATION<br/>[FR] COMPOSES ANTI-PICORNAVIRUS ET PROCEDES D'UTILISATION ET DE PREPARATION ASSOCIES
  申请人：——

  公开号：WO1999031122A1

  公开（公告）日：1999-06-24

  [EN] Picornaviral 3C protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of picornaviral 3C proteases. These compounds, as well as pharmaceutical compositions that contain these compounds, are suitable for treating patients or hosts infected with one or more picornaviruses. Several novel methods and intermediates can be used to prepare the novel picornaviral 3C protease inhibitors of the present invention.
  [FR] L'invention concerne des inhibiteurs des protéases 3C picornavirales, obtenus par synthèse chimique et qui inhibent ou bloquent l'activité biologique de ces protéases 3C picornavirales. Ces composés, de même que les compositions pharmaceutiques qui les contiennent sont conçus pour traiter des patients ou des hôtes infectés par un ou plusieurs picornavirus. L'invention concerne encore l'utilisation de plusieurs nouveaux procédés et intermédiaires dans la préparation de ces nouveaux inhibiteurs des protéases 3C picornavirales.
• 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.