4-hydroxy-2,3-dioxo-1,4-benzoxazine | 89898-78-2

• 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: 4-hydroxy-2,3-dioxo-1,4-benzoxazine
• 英文别名: 4-Hydroxy-2,3-dioxo-1,4-benzoxazin；4-hydroxy-4H-benzo[1,4]oxazine-2,3-dione；4-Hydroxy-2H-1,4-benzoxazine-2,3(4H)-dione；4-hydroxy-1,4-benzoxazine-2,3-dione
• CAS: 89898-78-2
• 化学式: C₈H₅NO₄
• 分子量: 179.132
• InChiKey: KRAHOMRDNAPXMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2,3-dioxo-1,4-benzoxazine 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以77%的产率得到2,4-二羟基-2H-1,4-苯并噁嗪-3(4h)-酮
  参考文献：
  名称：

  A New General Approach to the 2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one Skeleton via Diisobutylaluminum Hydride Reduction of 2,3-Dioxo-1,4-benzoxazines

  摘要：

  一系列天然半肟2a-d是通过化学选择性二异丁基氢化铝还原2,3-二氧代-4H-1,4-苯并恶嗪1a,b及其N-羟基衍生物1c,d前体合成的。所描述的工艺是一种新的通用方法，从2-羟基-2H-1,4-苯并恶嗪-3(4H)-酮骨架出发，仅通过三个步骤，从硝基苯酚开始，即可生成生物活性天然羟肟酸2,4-二羟基-2H-1,3(4H)-酮（2c）和2,4-二羟基-7-甲氧基-2H-1,4-苯并恶嗪-3(4H)-酮（2d）。

  DOI：

  10.1055/s-1993-25936
• 作为产物：
  描述：

  Ethyl o-Nitrophenyl Oxalate 在 Pt(S)/C 氢气 、 溶剂黄146 作用下， 以88%的产率得到4-hydroxy-2,3-dioxo-1,4-benzoxazine
  参考文献：
  名称：

  Syntheses of Cyclic Hydroxamic Acids and Lactams with 2,3-dioxo-1,4-benzoxazine skeleton

  摘要：

  Ethyl 2-nitrophenyl oxalate (1 a) and its 5-methoxy derivative (1 b) were subjected to catalytic hydrogenations over 3 % Pt (S) on carbon in different solvents. Thus, hydrogenation in acetic acid yielded 4-hydroxy-2,3-dioxo-1,4-benzoxazine (2a) and its 7-methoxy derivative (2 b) by reductive cyclization, the dehydro forms of the naturally occurring cyclic hydroxamic acids DIBOA and DIMBOA from Gramineae. In contrast, hydrogenation of esters 1 in methanol results in the formation of amides 3 by acyl group migration. On heating, amides 3 undergo lactonization to form lactone-lactames 4, which in turn undergo ring opening to give amides 3 when refluxed in ethanol.

  DOI：

  10.1002/prac.19933350409

文献信息

• Honkanen,E.; Virtanen,A.I., Acta Chemica Scandinavica (1947), 1960, vol. 14, p. 1214 - 1217
  作者：Honkanen,E.、Virtanen,A.I.

  DOI：——

  日期：——
• Syntheses of Cyclic Hydroxamic Acids and Lactams with 2,3-dioxo-1,4-benzoxazine skeleton
  作者：H. Hartenstein、D. Sicker

  DOI：10.1002/prac.19933350409

  日期：——

  Ethyl 2-nitrophenyl oxalate (1 a) and its 5-methoxy derivative (1 b) were subjected to catalytic hydrogenations over 3 % Pt (S) on carbon in different solvents. Thus, hydrogenation in acetic acid yielded 4-hydroxy-2,3-dioxo-1,4-benzoxazine (2a) and its 7-methoxy derivative (2 b) by reductive cyclization, the dehydro forms of the naturally occurring cyclic hydroxamic acids DIBOA and DIMBOA from Gramineae. In contrast, hydrogenation of esters 1 in methanol results in the formation of amides 3 by acyl group migration. On heating, amides 3 undergo lactonization to form lactone-lactames 4, which in turn undergo ring opening to give amides 3 when refluxed in ethanol.
• A New General Approach to the 2-Hydroxy-2<i>H</i>-1,4-benzoxazin-3(4<i>H</i>)-one Skeleton via Diisobutylaluminum Hydride Reduction of 2,3-Dioxo-1,4-benzoxazines
  作者：Dieter Sicker、Holger Hartenstein

  DOI：10.1055/s-1993-25936

  日期：——

  A series of naturally occurring hemiacetals 2a-d was synthesized by the chemoselective diisobutylaluminum hydride reduction of 2,3-dioxo-4H-1, 4-benzoxazines 1a,b and their N-hydroxy derivatives 1c,d precursors. The procedure described represents a new general approach to the 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one skeleton giving rise to the bioactive natural hydroxamic acids 2,4-dihydroxy-2H-1, 3(4H)-one (2c) and 2,4-dihydroxy-7-methoxy-2H-1, 4-benzoxazin-3(4H)-one (2d) in only three steps starting from nitrophenols.

  一系列天然半肟2a-d是通过化学选择性二异丁基氢化铝还原2,3-二氧代-4H-1,4-苯并恶嗪1a,b及其N-羟基衍生物1c,d前体合成的。所描述的工艺是一种新的通用方法，从2-羟基-2H-1,4-苯并恶嗪-3(4H)-酮骨架出发，仅通过三个步骤，从硝基苯酚开始，即可生成生物活性天然羟肟酸2,4-二羟基-2H-1,3(4H)-酮（2c）和2,4-二羟基-7-甲氧基-2H-1,4-苯并恶嗪-3(4H)-酮（2d）。