isonicotinic acid [7-hydroxy-4-methyl-2-oxo-2H-chromen-8-ylmethylene]hydrazide | 384843-29-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: isonicotinic acid [7-hydroxy-4-methyl-2-oxo-2H-chromen-8-ylmethylene]hydrazide
• 英文别名: N-[(7-hydroxy-4-methyl-2-oxochromen-8-yl)methylideneamino]pyridine-4-carboxamide
• CAS: 384843-29-2
• 化学式: C₁₇H₁₃N₃O₄
• 分子量: 323.308
• InChiKey: JHXUAULJBDCXFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 bis(acetylacetonato)dioxidomolybdenum(VI) 、 isonicotinic acid [7-hydroxy-4-methyl-2-oxo-2H-chromen-8-ylmethylene]hydrazide 反应 3.0h， 以95.6%的产率得到[Mo^VIO₂(fhmc-inh)(MeOH)]
  参考文献：
  名称：

  Oxidative bromination of monoterpene (thymol) using dioxidomolybdenum(VI) complexes of hydrazones of 8-formyl-7-hydroxy-4-methylcoumarin

  摘要：

  Condensation of equimolar amount of 8-formy1-7-hydroxy-4-methylcoumarin (fhmc) and hydrazides [benzoylhydrazide (bhz), isonicotinoylhydrazide (inh), nicotinoylhydrazide (nah) and furoylhydrazide (fah)] in methanol results in the formation of potential ONO tridentate ligands H(2)fhmc-bhz (I), H(2)fhmc-inh (II), H(2)fhmc-nah (III), and H(2)fhmc-fah (IV), respectively. Reaction of these ligands with [(MoO2)-O-vi(acac)(2)] in refluxing methanol gives dioxidomolybdenum(VI) complexes, [(MoO2)-O-vi(fhmc-bhz) (MeOH)] (1), [(MoO2)-O-vi(fhmc-inh)(MeOH)] (2), [(MoO2)-O-vi(fhmc-nah)(MeOH)] (3) and [(MoO2)-O-vi(fhmc-fah) (MeOH)] (4), respectively. The structures of the obtained ligand and their respective metal complexes were elucidated by elemental analyses, spectroscopic techniques (IR, electronic, H-1 and C-13 NMR) and thermogravimetric analyses. Single crystal X-ray analysis of complex 1a confirms the chelation of the ligand to the metal ion through two oxygen and a nitrogen atoms. These metal complexes have been tested against oxidative bromination of monoterpene (thymol) to yield 2-bromothymol, 4-bromothymol and 2,4-dibromothymol using H2O2 as an oxidant therefore they act as functional models of vanadium dependent haloperoxidases. The effects of various factors, such as amounts of catalyst, oxidant, KBr, HClO4 and different solvents have been considered to optimize the reaction conditions for the maximum brominated products. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.05.001
• 作为产物：
  描述：

  羟甲香豆素 以 乙醇 、 溶剂黄146 为溶剂， 反应 12.5h， 生成 isonicotinic acid [7-hydroxy-4-methyl-2-oxo-2H-chromen-8-ylmethylene]hydrazide
  参考文献：
  名称：

  从单一合成子[1]方便地一锅合成新的三环香豆素。

  摘要：

  本文报道了使用8-甲酰基-7-羟基-4-甲基香豆素作为单一合成子的高产率合成新的三环香豆素的方法。采用了不同的策略来合成在香豆素骨架中C7-C8位置与异恶唑和吡喃融合的三环香豆素。在吡唑基香豆素的构建过程中对官能团的修饰导致了新的氧化ipso硝化反应。所述Ô -tosylate进行的，在密封管试验压力条件下，由于不可能通过常规方法来代替香豆素7-羟基。本研究中合成的所有化合物均经IR，1 H-NMR，13表征C-NMR，ESI-MS和元素分析。一些中间的X射线衍射数据也在本文中报道。

  DOI：

  10.1002/jhet.1032