甲基3-苯基-2-氧杂氮丙啶羧酸酯 | 134920-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 甲基3-苯基-2-氧杂氮丙啶羧酸酯
• 中文别名: 2-噁吖丙啶羧酸,3-苯基-,甲基酯
• 英文名称: N-methoxycarbonyl-3-phenyloxaziridine
• 英文别名: Methyl 3-phenyloxaziridine-2-carboxylate
• CAS: 134920-16-4
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: ZAHRKOJKQBSMTP-UHFFFAOYSA-N

物化性质

• 沸点：
  234.9±43.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  甲基3-苯基-2-氧杂氮丙啶羧酸酯 在 水 作用下， 以 丙酮 为溶剂， 生成 N-methyl 1-hydroxy-1-phenylmethylcarbamate
  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
• 作为产物：
  描述：

  methyl N-phenylmethylenecarbamate 在 Oxone 作用下， 以70%的产率得到甲基3-苯基-2-氧杂氮丙啶羧酸酯
  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

• 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。
• Bicyclic and tricyclic .beta.-lactams
  申请人：Hoffmann-La Roche Inc.

  公开号：US05510343A1

  公开（公告）日：1996-04-23

  There are described compounds of the formula ##STR1## in which R signifies lower alkoxycarbonyl, lower alkoxycarbonylamino, the acyl residue of an .alpha.- or .beta.-amino acid or a residue of the general formula Q--X--Y-- (a) wherein Q signifies a 3- to 6-membered ring which optionally contains nitrogen, sulphur and/or oxygen and which is optionally bonded with a fused ring, X signifies a direct bond or a linear "spacer" with up to 6 atoms consisting of carbon, nitrogen, oxygen and/or sulphur, of which up to 2 atoms can be nitrogen atoms and 1 atom can be oxygen or sulphur, and Y represents one of the groups --CO--, --CS--, --CONH-- and (where X contains neither sulphur nor carbonyl as a terminal component) --SO.sub.2 --; and in which R.sup.1 signifies hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group containing nitrogen, sulphur and/or oxygen, and R.sup.2 represents the sulpho group --SO.sub.3 H or R.sup.1 and R.sup.2 together signify a group of the formula ##STR2## wherein A represents hydrogen or a residue which is usable in the 3-position of cephalosporin antibiotics, and in which R.sup.3 represents hydrogen or R.sup.1 and R.sup.3 together represent a group of the formula .dbd.CH--R.sup.a (c) wherein R.sup.a signifies one of the groups --COR.sup.b (c.sup.1) --CH.sub.2 --OCOR.sup.c (c.sup.2) --CH.sub.2 --NR.sup.d R.sup.e (c.sup.3) --CH.sub.2 --S--Het (c.sup.4) in which R.sup.b represents lower alkoxy or amino, R.sup.c represents lower alkyl, phenyl or amino, R.sup.d and R.sup.e each independently represent hydrogen or lower alkyl or R.sup.d and R.sup.e together with the N atom to which they are attached represent a 5- or 6-membered N-heterocycle which optionally contains a further nitrogen, oxygen or sulphur atom and Het represents a 5- or 6-membered heteroaromatic group containing nitrogen, sulphur and/or oxygen, and pharmaceutically compatible salts of these compounds. The products have .beta.-lactamase inhibiting properties. They are useful in combination with .beta.-lactam antibiotics in the control of .beta.-lactamase forming pathogens.

  该文描述了以下式子的化合物：##STR1## 其中R表示低烷氧羰基，低烷氧羰基氨基，α-或β-氨基酸的酰基残基或一般式Q-X-Y-的残基(a)，其中Q表示含有氮、硫和/或氧的3-至6-环，可以与融合环相结合，X表示直接键或由碳、氮、氧和/或硫组成的长达6个原子的线性“间隔物”，其中最多有2个原子可以是氮原子，1个原子可以是氧或硫，Y代表--CO--、--CS--、--CONH--和（当X不含硫或羰基作为末端组分时）--SO.sub.2--中的一种基团；其中R.sup.1表示氢、卤素、氨基甲酸酯氧、低烷酰氧或公式--S--Het的基团，其中Het表示含有氮、硫和/或氧的5-或6-成员杂环芳基基团，R.sup.2表示磺酰基--SO.sub.3H或R.sup.1和R.sup.2在一起表示公式##STR2##其中A表示氢或可用于头孢菌素类抗生素的3位的残基，R.sup.3表示氢或R.sup.1和R.sup.3在一起表示公式.dbd.CH--R.sup.a（c），其中R.sup.a表示下列基团之一--COR.sup.b（c.sup.1）--CH.sub.2--OCOR.sup.c（c.sup.2）--CH.sub.2--NR.sup.dR.sup.e（c.sup.3）--CH.sub.2--S--Het（c.sup.4），其中R.sup.b表示低烷氧或氨基，R.sup.c表示低烷基、苯基或氨基，R.sup.d和R.sup.e各自独立地表示氢或低烷基，或R.sup.d和R.sup.e与它们连接的N原子一起表示含有进一步氮、氧或硫原子的5-或6-成员N杂环，Het表示含有氮、硫和/或氧的5-或6-成员杂环芳基基团，以及这些化合物的药学兼容盐。该产品具有β-内酰胺酶抑制作用。它们与β-内酰胺类抗生素结合使用可控制β-内酰胺酶形成的病原体。
• Efficient nitrogen transfer from aldehyde-derived N-acyloxaziridines
  作者：Alan Armstrong、Ian D. Edmonds、Martin E. Swarbrick

  DOI：10.1016/s0040-4039(03)01200-0

  日期：2003.7

  The effect of solvent polarity on the reaction of 3-aryl-N-carboxamido- and 3-aryl-N-alkoxycarbonyl oxaziridines has been studied and an efficient procedure for high yielding sulfimidation developed by use of polar solvents. The first examples of asymmetric sulfimidation using novel chiral oxaziridines have been carried out with low diastereoselectivity (up to 30% de). (C) 2003 Elsevier Science Ltd. All rights reserved.
• Beta-Lactame
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0508234B1

  公开（公告）日：1996-07-24
• US5510343A
  申请人：——

  公开号：US5510343A

  公开（公告）日：1996-04-23