2,4-二羟基-2H-1,4-苯并噁嗪-3(4h)-酮 | 17359-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 2,4-二羟基-2H-1,4-苯并噁嗪-3(4h)-酮
• 英文名称: 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one
• 英文别名: 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one；4-hydroxy-2H-1,4-benzoxazin-3(4H)-one；2,4-dihydroxy-1,4-benzoxazin-3-one；2,4-dihydroxy-2H-benzoxazin-3-one；DIBOA；D-DIBOA
• CAS: 17359-54-5
• 化学式: C₈H₇NO₄
• 分子量: 181.148
• InChiKey: COVOPZQGJGUPEY-UHFFFAOYSA-N

物化性质

• 熔点：
  157-159℃
• 沸点：
  405.1±55.0 °C(Predicted)
• 密度：
  1.664±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少许）、DMSO（少许）、甲醇（少许）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 储存条件：
  温度：20°C，环境气体：惰性气体

反应信息

• 作为反应物：
  描述：

  2,4-二羟基-2H-1,4-苯并噁嗪-3(4h)-酮 反应 1.0h， 以1.8 mg的产率得到2-苯并唑啉酮
  参考文献：
  名称：

  Non-induced cyclic hydroxamic acids in wheat during juvenile stage of growth

  摘要：

  2,4-Dihydroxy-1,4-benzoxazine-3-one glucoside (DIBOA-G) and its methoxy analogue, 2,4-dihydroxy-7-methoxy-1,4-benzoxazine-3-one glucoside (DIMBOA-G), were present in germinating wheat (Triticum aestivum); the corresponding aglycones, DIBOA and DIMBOA, appeared soon after germination. The amounts of these compounds reached a maximum 12-48 hours after germination, and then decreased to undetectable levels as the plants began autotrophic growth. The time of their appearance was little affected by using seeds either sterilized or non-sterilized, by infection with pathogens and wounding with a razor blade. The concentration of DIBOA was found to be 0.2-0.3 nmol mg(-1) fr. wt (0.2-0.3 mM if the density of plant tissue is assumed to be uniform and unity) and that of DIMBOA was 0.7-1.0 nmol mg(-1) (0.7-1.0 mM). The aglycones retarded the germ tube growth of species of fungi at 0.3 mM. These observations suggest that the appearance of benzoxazinones is as defence compounds in the juvenile stage of growth. [C-14]Anthranilic acid was incorporated into DIBOA-G and DIMBOA-G when administered to embryos isolated from pre-emerging seeds, showing that the series of compounds are generated by de novo synthesis.

  DOI：

  10.1016/0031-9422(94)00831-d
• 作为产物：
  描述：

  4-羟基-2H-1,4-苯并噁嗪-3(4h)-酮 在 溴 、 silver carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 水 为溶剂， 反应 2.0h， 生成 2,4-二羟基-2H-1,4-苯并噁嗪-3(4h)-酮
  参考文献：
  名称：

  A Convenient Synthesis of 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one

  摘要：

  描述了合成 2,4-二羟基-2H-1.4-苯并恶嗪-3(4H)-酮 (6)（一种来自禾本科的生物活性天然产物）的便捷四步程序，避免了迄今为止现有方法的缺点，并提供了 6总产率60%。

  DOI：

  10.1055/s-1989-27203

文献信息

• Syntheses of 2-hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one: A precursor of a bioactive electrophile from Gramineae
  作者：Carlos A. Escobar、Michael Kluge、Dieter Sicker

  DOI：10.1016/s0040-4039(96)02492-6

  日期：1997.2

  2-Hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one (8), the hitherto undescribed free hemiacetalic aglycone of a benzoxazinoid acetal glucoside naturally occurring in wheat, has been synthesized following two pathways, independently. This cyclic hydroxamic acid methyl ester proved to be very unstable when in solution. This gives rise to the assumption that HDIBOA naturally released from its acetal

  已经合成了2-羟基-4,7-二甲氧基-2 H -1,4-苯并恶嗪-3（4 H）-one（8），这是小麦中天然存在的迄今未描述的苯并恶嗪样缩醛糖苷的游离半缩醛糖苷。两条途径，独立。证明该环状异羟肟酸甲酯在溶液中时非常不稳定。这引起这样的假设，即从其乙缩醛葡糖苷天然释放的HDIBOA是通过甲醇盐消除而形成多中心亲电试剂的前体，该亲电试剂最近被报道是苯并恶嗪样铅的生物活性成分。
• Novel compounds for use in weight loss and appetite suppression in humans
  申请人：——

  公开号：US20040192669A1

  公开（公告）日：2004-09-30

  Phenolic compounds with a phenolic molecule to which are covalently linked an oxygen-containing group, a nitrogen or another oxygen containing group, and a C 1 -C 4 alkoxy group, obtainable from monocotyledonous plants, or by chemical synthesis, have been found to act as weight loss agents, appetite suppressants, mood enhancers and adjunctive therapy for arthritis, sleep apnea, fibromyalgia, diabetes and hyperglycemia. Additional chemical compounds of the present invention may include benzoxazinoids-cyclic hydroxyamic acids, lactams, and corresponding glucosides, which may serve as precursors to phenolic compounds. The phenolic compounds and precursors of phenolic compounds of the present invention, at concentrations suitable for human therapeutic use, may be obtained from monocotyledonous plants such as corn in their early growth states which are timely harvested for optimum yield.

  从单子叶植物中获得的含有苯酚分子的苯酚化合物，其中与氧含有基团，氮或另一个氧含有基团以及C1-C4烷氧基共价连接，或通过化学合成，已被发现可作为减肥剂、食欲抑制剂、情绪增强剂和关节炎、睡眠呼吸暂停、纤维肌痛、糖尿病和高血糖的辅助治疗剂。本发明的其他化学化合物可能包括苯并噁唑啉-环状羟基酰胺、内酰胺和相应的葡萄糖苷，这些化合物可能作为苯酚化合物的前体。本发明的苯酚化合物和苯酚化合物的前体，在适合人类治疗使用的浓度下，可以从单子叶植物中获得，例如在它们的早期生长状态下收获以获得最佳产量的玉米。
• Occurrence and Characterization of 2-Hydroxy-1,4-benzoxazin-3-one and Indole Hydroxylases in Juvenile Wheat
  作者：Junya TANABE、Masayuki SUE、Atsushi ISHIHARA、Hajime IWAMURA

  DOI：10.1271/bbb.63.1614

  日期：1999.1

  precursor of DIBOA, and indole, the first intermediate of the biosynthetic pathway that branches off from the tryptophan pathway, by using microsomes prepared from wheat seedlings. Both hydroxylases occurred soon after germination, reached a maximum 48 h after germination, and decreased to finally disappear as the plants grew into the autotrophic growth stage. The mode of appearance and disappearance similar

  环状异羟肟酸2,4-二羟基-1,4-苯并恶嗪-3-酮（DIBOA）及其7-甲氧基类似物（DIMBOA）在幼年，非自养阶段小麦和玉米中大量瞬时出现。生长。为了阐明用于瞬时生产这些化合物的生物合成酶，我们研究了DIBOA的直接前体2-羟基-1,4-苯并恶嗪-3-酮（HBOA）和吲哚（其第一中间体）的羟基化活性。通过使用从小麦幼苗制备的微粒体，从色氨酸途径分支出来的生物合成途径。两种羟化酶在发芽后不久就发生，在发芽后最大达到48小时，并且随着植物生长进入自养生长阶段而减少直至最终消失。出现和消失的方式类似于异羟肟酸，提示吲哚后参与生物合成的整套酶的表达升高是造成异羟肟酸发生的原因。还观察到了1,4-苯并恶嗪-3-酮（一种假定的HBOA的前体）的羟化活性，但其程度明显低于HBOA和吲哚的羟化活性。
• α-Hydroxylation of cyclic hydroxamic acids by peroxide oxidation : A novel approach to allelochemicals from Gramineae
  作者：Holger Hartenstein、Dieter Sicker

  DOI：10.1016/s0040-4039(00)73347-8

  日期：1994.6

  Naturally occurring hemiacetals DIBOA and DIMBOA were synthesized by the first α-hydroxylation of N-hydroxylactams via m-chloroperbenzoic acid oxidation of corresponding cyclosilyl enol ethers.

  天然存在的半缩醛DIBOA和DIMBOA是通过N-羟基内酰胺通过相应的环甲硅烷基烯醇醚的间氯过苯甲酸的第一次α-羟基化反应合成的。
• The reduction of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one by thiols
  作者：Francisco J. Pérez、Hermann M. Niemeyer

  DOI：10.1016/0031-9422(85)80036-4

  日期：1985.11

  Abstract 2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), a naturally occurring hydroxamic acid involved in pest resistance of cereals, was reduced by thiols to the corresponding lactam. Kinetic studies showed that the reactive species are undissociated DIMBOA and thiolate anion. Possible mechanisms for the reaction are discussed in the light of relative reactivities of DIMBOA and a compound

  摘要 2,4-二羟基-7-甲氧基-1,4-苯并恶嗪-3-one (DIMBOA) 是一种天然存在的与谷物抗虫性有关的异羟肟酸，可被硫醇还原为相应的内酰胺。动力学研究表明，活性物质是未解离的 DIMBOA 和硫醇盐阴离子。根据 DIMBOA 和缺少 7-甲氧基取代基的化合物的相对反应性讨论了该反应的可能机制，并从分子轨道计算得出结果。