3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dione | 1217-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dione
• 英文别名: 3-Phenyl-2H-1,3-benzoxazin-2,4(3H)-dion；3-Phenyl-2,4-dioxo-3,4-dihydro-2H-1,3-benzoxazin；3-phenyl-1,3-benzoxazine-2,4-dione
• CAS: 1217-25-0
• 化学式: C₁₄H₉NO₃
• 分子量: 239.23
• InChiKey: AIPDYRUQGNTLLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dione 、 Ammonium hydroxide 生成 水杨酰苯胺
  参考文献：
  名称：

  Bogisch, Dissert. , S. 29

  摘要：

  DOI：
• 作为产物：
  描述：

  (2-氰基苯基)N-苯基氨基甲酸酯 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 反应 27.0h， 生成 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dione
  参考文献：
  名称：

  Petridou-Fischer, J.; Papadopoulos, E. P., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1159 - 1167

  摘要：

  DOI：

文献信息

• Intrinsic Gas-Phase Reactivity of Ionized 6-(Oxomethylene)cyclohexa-2,4-dienone:  Evidence Pointing to Its Neutral α-Oxoketene Counterpart as a Proper Precursor of Various Benzopyran-4-ones and Analogues
  作者：Paulo Sergio de Carvalho、Fabiane M. Nachtigall、Marcos Nogueira Eberlin、Luiz Alberto Beraldo Moraes

  DOI：10.1021/jo070371z

  日期：2007.8.1

  structure and potential use as an important building block in organic synthesis, the title α-oxoketene 1 has been formed mostly under very special conditions as a short-lived species. The reactivity of 1 is, therefore, nearly unexplored. In great contrast, it seemed that its ionized gaseous form 1•+ is stable and easily accessible. In this study, we used multiple-stage pentaquadrupole mass spectrometry to probe

  尽管其独特的结构和作为有机合成重要组成部分的潜在用途，但标题α-氧杂环丁烯1大多是在非常特殊的条件下作为短命物种形成的。因此，几乎没有探索1的反应性。与之形成鲜明对比的是，它的离子化气态1 • +似乎是稳定且易于获得的。在这项研究中，我们使用了多级五四极杆质谱法来探测气态1 • +的形成，并探讨其稳定性和固有反应性。与水和甲醇一起，发现气态1 • +与溶剂化1的反应相似，这表明它们的反应性之间存在密切的相似之处。还发现气态1 • +会通过极性[3 + 2]环加成环迅速与各种双亲物（包括烯烃，炔烃，异氰酸酯，酮和酯）反应，从而形成一系列苯并吡喃-4-酮（黄酮，4-色酮，4 -chromenones，苯并[1,3]二恶英-4-酮和类似物）是许多天然产物中常见的结构单元。本可用性1在室温和气相发现用于本发明的气态报道1 • +表明溶剂化1应该接受许多[4 + 2]环加成，并且用作各种生物活性分子的通用前体。
• Derivatives of 1,3,5-triazine—I Condensation of o-hydroxybenzanilides with cyanuric chloride and fission of the triazine ring
  作者：B.S. Joshi、R. Srinivasan、R.V. Talavdekar、K. Venkataraman

  DOI：10.1016/0040-4020(60)80062-2

  日期：1960.1

  The condensation of cyanuric chloride with o-hydroxybenzanilides takes place on the amide nitrogen. Treatment of the condensation products with acetic anhydride and pyridine opens the triazine ring and yields benzoxazine derivatives, whose structures are discussed.

  氰尿酰氯与邻羟基苯甲酰肼的缩合在酰胺氮上发生。用乙酸酐和吡啶处理缩合产物可打开三嗪环并生成苯并恶嗪衍生物，其结构已得到讨论。
• New Groups of Potential Antituberculotics: 3-Aryl-2H,4H-benz[e][1,3]oxazine-2,4-diones. Comparison of the Topliss Approach with Regression Analysis
  作者：Karel Waisser、Lenka Kubicová、Věra Klimešová、Želmíra Odlerová

  DOI：10.1135/cccc19932977

  日期：——

  3-Phenyl-2H,4H-benz[e][1,3]oxazine-2,4-dione (I) and its derivatives II - XI, substituted on the phenyl ring, can be regarded as a new group of potential antituberculotics. Their activity increases with increasing electron-accepting properties of the substituents. introduction of bromine into the position 6 also positively influences the activity. the compounds are active in vitro against Mycobacterium tuberculosis and M. kansasii. The activity of some of them (VIII, IX0 exceeds that of commercial tuberculostatics used as standards.

  3-苯基-2H,4H-苯[e][1,3]噁嗪-2,4-二酮(I)及其苯环上取代的衍生物II-XI，可视为一组新的潜在抗结核药物。随着取代基电子受体性质的增加，它们的活性也会增加。在位置6引入溴也会对活性产生积极影响。这些化合物在体外对结核分枝杆菌和堪萨斯分枝杆菌具有活性。其中一些化合物(VIII，IX)的活性超过了作为标准使用的商业抗结核药物。
• Multivariate Regression with Substituent Shift Increments. IV. 2-(4-X-Phenyl)-1,3-dihydro-2H-isoindole-1,3-diones and 3-(4-X-Phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones
  作者：Miroslav Holík、Zdeněk Friedl、Karel Waisser、Jiří Gregor

  DOI：10.1135/cccc19991709

  日期：——

  Two series of para disubstituted benzenes were studied: 2-(4-X-phenyl)-1,3-dihydro- 2H-isoindole-1,3-diones (1) and 3-(4-X-phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones (2). Their ¹H and ¹³C chemical shifts were correlated with substituent shift increments (SSI) a_j and z_j, respectively. For ¹³C chemical shifts, all four z_j values, z_i, z_o, z_m, and z_p, were used to check the assignment and to find out possible variables for improvement of regression equations. Significant deviations from plain additivity were observed in the case of δ_H3 and δ_C3 chemical shifts. This can be explained by changes in diamagnetic anisotropy contribution induced by different twist of 4-substituent from the benzene plane caused by variable substituent in position 1.

  研究了两组para二取代苯：2-(4-X-苯基)-1,3-二氢-2H-异吲哚-1,3-二酮(1)和3-(4-X-苯基)-3,4-二氢-2H-1,3-苯并噁嗪-2,4-二酮(2)。它们的¹H和¹³C化学位移与取代基位移增量(SSl) a_j和z_j相关。对于¹³C化学位移，所有四个z_j值，z_i，z_o，z_m和z_p，都被用来检查分配并找出可能改进回归方程的变量。在δ_H3和δ_C3化学位移的情况下观察到明显的偏离简单加性。这可以通过由位于位置1的可变取代基引起的苯环平面外4-取代基的不同扭曲引起的抗磁性异向贡献的变化来解释。
• Nickel-catalyzed [4 + 2] Cycloaddition of Alkynes to Carbonylsalicylamides via Elimination of Isocyanates
  作者：Yasufumi Yoshino、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1246/cl.2010.896

  日期：2010.8.5

  An intermolecular nickel-catalyzed [4 + 2] cycloaddition has been developed where carbonylsalicylamides react with alkynes to afford substituted chromones. The reaction involves an elimination of i...

  已开发出分子间镍催化的 [4 + 2] 环加成反应，其中羰基水杨酰胺与炔烃反应生成取代的色酮。该反应涉及消除我...

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