4-(4-nitrobenzylidene)-2-(4-nitrophenyl)-5(4H)-oxazolone | 313973-01-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(4-nitrobenzylidene)-2-(4-nitrophenyl)-5(4H)-oxazolone
• 英文别名: 2-(4-Nitrophenyl)-4-[(4-nitrophenyl)methylidene]-1,3-oxazol-5-one
• CAS: 313973-01-2
• 化学式: C₁₆H₉N₃O₆
• mdl: MFCD00380601
• 分子量: 339.264
• InChiKey: UJHUBBOQWDIWCG-UHFFFAOYSA-N

物化性质

• 熔点：
  310 °C(Solv: acetic acid (64-19-7))
• 沸点：
  509.1±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(4-nitrobenzylidene)-2-(4-nitrophenyl)-5(4H)-oxazolone 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 以 neat (no solvent) 为溶剂， 反应 2.0h， 以77%的产率得到
  参考文献：
  名称：

  氮杂内酯与DBU或DBN的独特级联开环/环化反应：合成新的吡咯仑A类似物

  摘要：

  通过1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）或1,5-的简单级联反应可有效合成1-Azabicyclo [3.3.0] oct-3-en-2-one衍生物带有亚芳基a内酯的二氮杂双环[4.3.0]非-5-烯（DBN）。该研究提供了一种新颖的合成具有良好抗菌活性的新型多环半生物碱的方法。在无催化剂，温和和无溶剂的条件下，可以高收率获得各种稠合的三环衍生物。

  DOI：

  10.1016/j.tet.2017.01.036
• 作为产物：
  描述：

  2-[(4-硝基苯甲酰基)氨基]乙酸乙酯 在 水 、 sodium acetate 、 乙酸酐 、 sodium hydroxide 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 5.0h， 生成 4-(4-nitrobenzylidene)-2-(4-nitrophenyl)-5(4H)-oxazolone
  参考文献：
  名称：

  Substituents Effect on the Erlenmeyer−Plöchl Reaction: Understanding an Observed Process Reaction Time

  摘要：

  A systematic study on hippuric acid substituents was performed in order to better understand the influence of stereoelectronic factors on the Erlenmeyer reaction rate. In addition, two reaction systems were evaluated: Hunig's base solvent free conditions and catalytic sodium acetate in 2-methyl-THF. The effect on reaction rate of electron withdrawing and electron donating groups are reported. Specifically, the study led to the conclusion that stereoelectronic factors have significant influence in one of our key Erlenmeyer reaction by affecting its reaction rate.

  DOI：

  10.1021/op100032s

文献信息

• CsF-Catalyzed Transannulation Reaction of Oxazolones: Diastereoselective Synthesis of Diversified <i>trans</i>-<i>N</i>-(6-Oxo-1,4,5,6-tetrahydropyrimidin-5-yl)benzamides with Arylidene Azlactones and Amidines
  作者：Golnaz Parhizkar、Ahmad Reza Khosropour、Iraj Mohammadpoor-Baltork、Elahehnaz Parhizkar、Hadi Amiri Rudbari

  DOI：10.1021/acscombsci.8b00027

  日期：2018.6.11

  straightforward synthetic strategy for the construction of new tetrasubstituted 1,3-diazinones is described. The procedure is based on CsF-catalyzed, microwave-assisted, ring transformation reaction of arylidene azlactones with amidines. Moreover, this technique provides diversified trans-N-(6-oxo-1,4,5,6-tetrahydropyrimidin-5-yl)benzamides with a good antimicrobial activity.

  描述了一种用于构建新的四取代的1，3-二氮杂二酮的通用且直接的合成策略。该程序基于CsF催化的亚芳基a内酯与am的微波辅助环转化反应。此外，该技术提供了多元化反式- ñ - （6-氧代-1,4,5,6-四氢嘧啶-5-基）具有良好的抗微生物活性的苯甲酰胺。
• Substituents Effect on the Erlenmeyer−Plöchl Reaction: Understanding an Observed Process Reaction Time
  作者：Flavio Chavez、Nicole Kennedy、Thimma Rawalpally、R. Thomas Williamson、Thomas Cleary

  DOI：10.1021/op100032s

  日期：2010.5.21

  A systematic study on hippuric acid substituents was performed in order to better understand the influence of stereoelectronic factors on the Erlenmeyer reaction rate. In addition, two reaction systems were evaluated: Hunig's base solvent free conditions and catalytic sodium acetate in 2-methyl-THF. The effect on reaction rate of electron withdrawing and electron donating groups are reported. Specifically, the study led to the conclusion that stereoelectronic factors have significant influence in one of our key Erlenmeyer reaction by affecting its reaction rate.
• Unique cascade ring-opening/cyclization reaction of azlactones and DBU or DBN: Synthesis of new pyrrolam A analogues
  作者：Golnaz Parhizkar、Ahmad Reza Khosropour、Iraj Mohammadpoor-Baltork、Elahehnaz Parhizkar、Hadi Amiri Rudbari

  DOI：10.1016/j.tet.2017.01.036

  日期：2017.3

  facile cascade reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) with arylidene azlactones. This research provides a straightforward procedure for the synthesis of a novel class of multicyclic semi-alkaloids which shows good antimicrobial activity. Under catalyst-free, mild, and solventless condition, a wide range of fused tricyclic derivatives was obtained

  通过1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）或1,5-的简单级联反应可有效合成1-Azabicyclo [3.3.0] oct-3-en-2-one衍生物带有亚芳基a内酯的二氮杂双环[4.3.0]非-5-烯（DBN）。该研究提供了一种新颖的合成具有良好抗菌活性的新型多环半生物碱的方法。在无催化剂，温和和无溶剂的条件下，可以高收率获得各种稠合的三环衍生物。