2H,4H-4-hydroxy-2-phenylbenzo[b]-1,4-oxazin-3-one | 1075211-23-2

• 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: 2H,4H-4-hydroxy-2-phenylbenzo[b]-1,4-oxazin-3-one
• 英文别名: 2-phenyl-D-DIBOA；2-Ph-D-DIBOA；4-hydroxy-2-phenyl-1,4-benzoxazin-3-one
• CAS: 1075211-23-2
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: AZUJQOFGMBURBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl α-(2-nitrophenoxy)phenylacetate 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 2H,4H-4-hydroxy-2-phenylbenzo[b]-1,4-oxazin-3-one
  参考文献：
  名称：

  Modified Benzoxazinones in the System Oryza sativa−Echinochloa crus-galli: An Approach to the Development of Biorational Herbicide Models

  摘要：

  The utility of benzoxazinones and some of their synthetic derivatives in the search for new leads for herbicide model development has been explored. The work described focuses on obtaining derivatives that present selectivity in the system Oryza sativa-Echinochloa crus-galli. To achieve this goal the influence of lipophilicity in this system has been studied by preparing 14 ester derivatives at the N-4 position of D-DIBOA along with other compounds with different functionalization and chain lengths at position C-2. These compounds have been tested in the aforementioned system, and the dose-response profiles have been compared. The most active compound was 2-ethyl-4-hydroxy(2H)-1,4-benzoxazin-3(4H)-one, which presented higher selectivity than the specific herbicide Cotanil-35. These results confirm the potential of D-DIBOA as a lead herbicide for the control of Echinochloa spp. in rice crops.

  DOI：

  10.1021/jf802735m

文献信息

• 10.1039/d4cc02118e
  作者：Winter, Johannes、Lühr, Susan、Hochadel, Kyra、Gálvez-Vázquez, María de Jesús、Prenzel, Tobias、Schollmeyer, Dieter、Waldvogel, Siegfried R.

  DOI：10.1039/d4cc02118e

  日期：——

  The electrochemical reduction of nitroarenes allows direct access to manifold nitrogen containing heterocycles. This work reports the simple and direct electro-organic synthesis of 18 different examples of 2H,4H-4-hydroxy-1,4-benzoxazin-3-ones in up to 81% yield. The scalability of the method was demonstrated on a gram-scale.

  硝基芳烃的电化学还原允许直接获得多种含氮杂环。这项工作报道了 18 种不同的 2 H ,4 H -4-羟基-1,4-苯并恶嗪-3-酮的简单直接的有机电合成，产率高达 81%。该方法的可扩展性在克级上得到了证明。
• Modified Benzoxazinones in the System <i>Oryza sativa</i>−<i>Echinochloa crus-galli</i>: An Approach to the Development of Biorational Herbicide Models
  作者：Francisco A. Macías、Nuria Chinchilla、Rosa M. Varela、José M. G. Molinillo、David Marín、João M. De Siqueira

  DOI：10.1021/jf802735m

  日期：2008.11.12

  The utility of benzoxazinones and some of their synthetic derivatives in the search for new leads for herbicide model development has been explored. The work described focuses on obtaining derivatives that present selectivity in the system Oryza sativa-Echinochloa crus-galli. To achieve this goal the influence of lipophilicity in this system has been studied by preparing 14 ester derivatives at the N-4 position of D-DIBOA along with other compounds with different functionalization and chain lengths at position C-2. These compounds have been tested in the aforementioned system, and the dose-response profiles have been compared. The most active compound was 2-ethyl-4-hydroxy(2H)-1,4-benzoxazin-3(4H)-one, which presented higher selectivity than the specific herbicide Cotanil-35. These results confirm the potential of D-DIBOA as a lead herbicide for the control of Echinochloa spp. in rice crops.