6-Oxo-5-phenyl-6H-[1,3,4]oxadiazine-2-carboxylic acid methyl ester | 98171-26-7

• 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: 6-Oxo-5-phenyl-6H-[1,3,4]oxadiazine-2-carboxylic acid methyl ester
• 英文别名: methyl 6-oxo-5-phenyl-6H-1,3,4-oxadiazine-2-carboxylate；methyl 6-oxo-5-phenyl-1,3,4-oxadiazine-2-carboxylate
• CAS: 98171-26-7
• 化学式: C₁₁H₈N₂O₄
• 分子量: 232.196
• InChiKey: DFABJSQTNOODIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-Oxo-5-phenyl-6H-[1,3,4]oxadiazine-2-carboxylic acid methyl ester 在 三氟化硼乙醚 作用下， 以 四氯化碳 为溶剂， 反应 1.25h， 生成 6-oxo-5-phenyl-6H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Christl, Manfred; Bodenschatz, Gabriele; Feineis, Erich, Liebigs Annalen, 1996, # 5, p. 853 - 861

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(Methoxyoxalylhydrazono)-2-phenylessigsaeure 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以51%的产率得到6-Oxo-5-phenyl-6H-[1,3,4]oxadiazine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Christl, Manfred; Lanzendoerfer, Ulrike; Groetsch, Maria M., Chemische Berichte, 1990, vol. 123, # 10, p. 2031 - 2037

  摘要：

  DOI：

文献信息

• Überbrückte neungliedrige α,β-ungesägttigte enollactone - synthese aus 5-phenyl-1,-3,-4,-oxadiazin-6-on-2-carbonsäure-methylester und konfigurationsanalyse
  作者：Manfred Christl、Joachim Hegmann、Horst Reuchlein、Karl Peters、Eva-Maria Peters、Hans Georg von Schnering

  DOI：10.1016/s0040-4039(00)96880-1

  日期：1987.1

  The γ-oxoketenes, which are formed from oxadiazinone 3a and strained cyclopentene derivatives, are shown to undergo a pericyclic ring enlargement to give the title compounds 2a, 2b and 5. In the case of 5, two configurations, one having a and the other a lactone functionality, are in equilibrium.

  由恶二嗪酮3a和应变的环戊烯衍生物形成的γ-氧杂环丁烷显示经过环周扩环，得到标题化合物2a，2b和5。在5的情况下，两种构型处于平衡，一种具有a ，另一种具有内酯官能度。
• Intramolekulare [2+2]-cycloadditionen von γ-oxoketenen
  作者：Joachim Hegmann、Manfred Christl、Karl Peters、Eva-Maria Peters、Hans Georg von Schnering

  DOI：10.1016/s0040-4039(00)96879-5

  日期：1987.1

  The γ-oxoketenes, which are accessible from methyl 1,3,4-oxadiazin-6-one-2-carboxylate-1 and cycloalkenes, are shown to undergo an intramolecular [2+2] cycloaddition either on heating or on photolysis to give different stereoisomers of β-lactones of the 3-oxo-2-oxabicyclo[2.2.0]hexane-type.

  可以从1,3,4-恶二嗪-6-一-2-羧酸酯-1和环烯烃获得的γ-氧杂环丁烷在加热或光解过程中会发生分子内[2 + 2]环加成反应，从而生成3-氧代-2-氧杂双环[2.2.0]己烷型β-内酯的不同立体异构体。
• Feineis, Erich; Schwarz, Harmut; Hegmann, Joachim, Chemische Berichte, 1993, vol. 126, # 7, p. 1743 - 1748
  作者：Feineis, Erich、Schwarz, Harmut、Hegmann, Joachim、Christl, Manfred、Peters, Eva-Maria、et al.

  DOI：——

  日期：——
• Cycloadditionen von 6H-1,3,4-Oxadiazin-6-onen (4,5-Diaza-?-Pyronen). 14. Nicht katalysierte und durch Trifluoressigs�ure katalysierte Reaktionen von 6H-1,3,4-Oxadiazin-6-onen mit Norbornen
  作者：Manfred Christl、Gabriele Bodenschatz、Erich Feineis、Joachim Hegmann、Gerhard H�ttner、Stefan Mertelmeyer、Klaus Sch�tzlein、Hartmut Schwarz

  DOI：10.1002/prac.199533701140

  日期：——

  In 11 out of 13 non-catalysed reactions of oxadiazinones 1 with norbornene, gamma-oxoketenes 4 were observed and could be isolated in three cases (4b,d,m). Except for 4m, all gamma-oxoketenes isomerised to enollactones of type 5 on thermolysis. However, 4b furnished the cyclobutene derivative 10 as the major product. No gamma-oxoketenes were detected in the reactions of Ik and 11, which gave rise to the formation of 5k and the enollactone 19, respectively. The latter was converted into 51 on treatment with trifluoroacetic acid (TFA). Four oxadiazinones 1 were allowed to react with norbornene in the presence of TFA. Three of them (1a,b,l) afforded mixtures of enollactones of type 5 and their diastereomers 12. Heating of 4 in the presence of norbornene led to the formation of the symmetrical delta-lactones 6. This process was observed to be efficient only where the conversion 4 --> 5 is slow (4b) or inoperative (4m). In five cases, the treatment of the components with boron trifluoride etherate proved to be a useful preparative alternative (6a,d,g,h,m). On treatment of 4a with methanol, the pseudoester 7a was formed, whereas 4b gave mixtures of 7b and the esters 8b and 15. Hydrogen chloride converted 4b into the pseudochloride 14, which furnished pseudoester 7b on methanolysis. Reaction of 4b,m with formic acid gave rise to pseudoanhydrides of type 13. From 4b and TFA a mixture of the enollactones 5b and 12b was obtained. Boron trifluoride etherate transformed 4i to enollactone 12i; analogously, 12m resulted on treatment of 4m with trifluoromethanesulfonic acid.
• Christl, Manfred, Gazzetta Chimica Italiana, 1986, vol. 116, # 1, p. 1 - 18
  作者：Christl, Manfred

  DOI：——

  日期：——

表征谱图