N-tert-butoxycarbonyl-3-(2,4-dichlorophenyl)oxaziridine | 163226-30-0

• 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-tert-butoxycarbonyl-3-(2,4-dichlorophenyl)oxaziridine
• 英文别名: Tert-butyl 3-(2,4-dichlorophenyl)oxaziridine-2-carboxylate
• CAS: 163226-30-0
• 化学式: C₁₂H₁₃Cl₂NO₃
• 分子量: 290.146
• InChiKey: RZOATXDPKXGQDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  317.5±52.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  吗啉 、 N-tert-butoxycarbonyl-3-(2,4-dichlorophenyl)oxaziridine 以 异丙醚 为溶剂， 反应 24.0h， 以77%的产率得到N-(tert-butoxycarbonylamino)morpholine
  参考文献：
  名称：

  亲电胺化试剂：制备3-芳基-N-BOC（或N-FMOC）恶唑烷的新方法

  摘要：

  通过在非质子条件下与间氯过氧苯甲酸锂反应，将N-BOC或N-FMOC苯甲二胺氧化为相应的3-芳基-N-BOC或N-FMOC恶唑烷。新的氧氮环丙烷可以在其N-BOC或N-FMOC基团转移到吗啉，得到相应的N β -保护的肼。

  DOI：

  10.1016/0040-4039(95)00025-8
• 作为产物：
  描述：

  N-BOC-脒三苯基膦 在 LiMCPBA 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 88.0h， 生成 N-tert-butoxycarbonyl-3-(2,4-dichlorophenyl)oxaziridine
  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

• DERIVES D'ALFA-HYDRAZINOACIDES ET PROCEDE POUR LES FABRIQUER
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：EP0853612B1

  公开（公告）日：2000-06-14
• US5962722A
  申请人：——

  公开号：US5962722A

  公开（公告）日：1999-10-05
• [EN] ALPHA-HYDRAZINO ACID DERIVATIVES AND METHOD FOR MAKING SAME<br/>[FR] DERIVES D'ALFA-HYDRAZINOACIDES ET PROCEDE POUR LES FABRIQUER
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：WO1997009303A1

  公开（公告）日：1997-03-13

  (EN) An $g(a)-hydrazino acid derivative of general formula (I) is described, wherein R1, R2, R3 are hydrogen or a carbon radical, such that when R2 and R3 are different, C* is an asymmetric carbon of L, D or DL configuration, and R4 and R5 are a protecting group, characterised in that R4 is a benzyl ArCH2 radical of formula (a), wherein Ar is a phenyl radical or phenyl substituted by one or more X groups; X being hydrogen, halogen, a nitro or alkyl radical; and in that R5 is a Y-O-CO group, where Y is a carbon radical different from R4.(FR) Dérivé d'$g(a)-hydrazinoacide de formule générale (I), dans laquelle R1, R2, R3 désignent l'hydrogène ou un radical carboné, lorsque R2 et R3 sont différents, C* désigne un carbone asymétrique de configuration L, D ou DL, R4 et R5 désignent un groupe protecteur, caractérisé: en ce que R4 désigne un radical benzyle ArCH2 de formule (a), où Ar désigne un radical phényle ou phényle substitué par un ou plusieurs groupes X; où X désigne l'hydrogène, un halogène, un radical nitro ou un radical alkyle; et en ce que R5 désigne un groupe Y-O-CO, dans lequel Y désigne un radical carboné différent de R4.
• 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.
• Electrophilic amination reagents: A new method for the preparation of 3-Aryl-N-BOC (or N-FMOC) oxaziridines
  作者：Joe¨lle Vidal、Ste´phanie Damestoy、Andre´ Collet

  DOI：10.1016/0040-4039(95)00025-8

  日期：1995.2

  N-BOC or N-FMOC benzaldimines are oxidized to the corresponding 3-Aryl-N-BOC or N-FMOC oxaziridines by reaction with Li m-chloroperoxybenzoate under aprotic conditions. The new oxaziridines can transfer their N-BOC or N-FMOC group to morpholine to give the corresponding Nβ-protected hydrazines.

  通过在非质子条件下与间氯过氧苯甲酸锂反应，将N-BOC或N-FMOC苯甲二胺氧化为相应的3-芳基-N-BOC或N-FMOC恶唑烷。新的氧氮环丙烷可以在其N-BOC或N-FMOC基团转移到吗啉，得到相应的N β -保护的肼。