2-methyl-5-phenyl-1,3,4-oxadiazin-6-one | 97130-20-6

• 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: 2-methyl-5-phenyl-1,3,4-oxadiazin-6-one
• CAS: 97130-20-6
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: IXYFRBIDWYHWFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  51
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-5-phenyl-1,3,4-oxadiazin-6-one 在 aluminum oxide 、 silica gel 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 2.0h， 生成 (1S*,2R*,3R*,4R*,αS*)-<3-Acetylbicyclo<2.2.1>hept-2-yl>phenylessigsaeure
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1002/prac.199533701140
• 作为产物：
  描述：

  (E)-2-(2-乙酰肼基)-2-苯乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 2-methyl-5-phenyl-1,3,4-oxadiazin-6-one
  参考文献：
  名称：

  Padwa, Albert; Eisenbarth, Philipp, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 61 - 64

  摘要：

  DOI：

文献信息

• Diels-alder cycloadditions of 1,3,4,-oxadiazin-6-ones with electron rich pi systems
  作者：Albert Padwa、Philipp Eisenbarth

  DOI：10.1016/s0040-4020(01)96420-8

  日期：1985.1

  cycloaddition behavior of several 2,5-disubstituted 1,3,4-oxadiazin-6-ones with electron rich pi bonds has been carried out. -1-Propenylpyrrolidine was found to react with the oxadiazinone ring system to give rise to a ring opened diazatrienyl substituted carboxylic acid. Further heating of the acid results in decarboxylation, hydrolysis, cyclization and pyrrolidine elimination to produce a disubstituted

  已经进行了几个具有富电子π键的2，5-二取代的1，3，4-恶二嗪-6-的环加成反应的研究。 发现-1-丙烯基吡咯烷与恶二嗪酮环系统反应，生成开环的二氮杂三烯基取代的羧酸。酸的进一步加热导致脱羧，水解，环化和吡咯烷消除，从而产生二取代的吡唑。还详细研究了与三取代的烯胺1-（2-甲基-丙烯基）吡咯烷的反应。遇到的环加成反应可以通过以下方法合理化：首先进行Diels-Alder反应，然后通过氮的偏向挤出法制得酮酮中间产物。烯酮的命运明显取决于取代的整体模式。所形成的一些产物可以通过吡咯烷基基团向乙烯酮和苯甲酰基的竞争性迁移来解释。
• Christl, Manfred; Bodenschatz, Gabriele; Feineis, Erich, Liebigs Annalen, 1996, # 5, p. 853 - 861
  作者：Christl, Manfred、Bodenschatz, Gabriele、Feineis, Erich、Hegmann, Joachim、Huettner, Gerhard、Mertelmeyer, Stefan、Schaetzlein, Klaus

  DOI：——

  日期：——
• Christl, Manfred, Gazzetta Chimica Italiana, 1986, vol. 116, # 1, p. 1 - 18
  作者：Christl, Manfred

  DOI：——

  日期：——
• PADWA, A.;EISENBARTH, PH., J. HETEROCYCL. CHEM., 1985, 22, N 1, 61-64
  作者：PADWA, A.、EISENBARTH, PH.

  DOI：——

  日期：——
• PADWA, A.;EISENBARTH, PH., TETRAHEDRON, 1985, 41, N 2, 283-296
  作者：PADWA, A.、EISENBARTH, PH.

  DOI：——

  日期：——