4,5-dihydro-3-hydroxy-1-phenylpyridazin-6-one | 61446-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4,5-dihydro-3-hydroxy-1-phenylpyridazin-6-one
• 英文别名: 3,6-Pyridazinedione, tetrahydro-1-phenyl-；1-phenyldiazinane-3,6-dione
• CAS: 61446-43-3
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: LVGKXNPVUJDONV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-3-hydroxy-1-phenylpyridazin-6-one 在 lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.0h， 生成 4-(2-Methoxy-ethyl)-1-phenyl-tetrahydro-pyridazin-3-one
  参考文献：
  名称：

  5-Lipoxygenase inhibitors: the synthesis and structure-activity relationships of a series of 1-phenyl-3-pyrazolidinones

  摘要：

  A series of analogues of the 5-lipoxygenase inhibitor 1-phenyl-3-pyrazolidinone (phenidone, 1a) has been prepared via two complementary new synthetic methods. The reaction of various electrophiles with the dianion of 1a or with an N-silylpyrazolidinone anion gave the desired 4-substituted pyrazolidinones (Scheme I and II). A new procedure was developed for the resolution of 4-substituted pyrazolidinones (Scheme V). A regression study on 21 compounds in this series showed a correlation of increased inhibitor potency (pIC50) with increased compound lipophilicity (log P) and with an N-phenyl electronic effect as measured by the C-13 NMR chemical shift parameter CNMR1' (R2 = 0.79). The most potent 5-lipoxygenase inhibitor in this series was 4-(ethylthio)-1-phenyl-3-pyrazolidinone (1n) with an IC50 of 60 nM. Another member of this series, 4-(2-methoxyethyl)-1-phenyl-3-pyrazolidinone (1f, IC50 = 0-48-mu-M), although less potent than 1n, was better tolerated in the whole animal relative to phenidone (1a) and also displayed good oral activity in two models of 5-lipoxygenase inhibition. On the basis of a structure-activity relationship study, a mechanism for the inhibition of 5-lipoxygenase by this class of inhibitors was proposed.

  DOI：

  10.1021/jm00109a006
• 作为产物：
  描述：

  methyl 4-oxo-4-(2-phenylhydrazinyl)butanoate 生成 4,5-dihydro-3-hydroxy-1-phenylpyridazin-6-one
  参考文献：
  名称：

  BELYX, Z. D.;PROTASOVA, E. A.;BRIGADNOVA, E. V., XIMIYA ORGAN. SOEDIN. AZOTA, PERM, 1981, 114-118

  摘要：

  DOI：

文献信息

• Improved synthesis of pyridazinediones under microwave irradiation
  作者：Line Bourel、André Tartar、Patricia Melnyk

  DOI：10.1016/0040-4039(96)00743-5

  日期：1996.6

  Pyridazinediones have been synthesized with good to excellent yields under microwave irradiation. The results were compared with traditional stirring.

  在微波辐射下已以良好至优异的产率合成了哒嗪二酮。将结果与传统搅拌进行比较。
• Process for producing chlorophenylhydrazine compounds
  申请人：KONICA CORPORATION

  公开号：EP0208477A1

  公开（公告）日：1987-01-14

  A process for producing a chlorophenylhydrazine compound is disclosed, which comprises chlorinating at least one hydrogen atom on the phenyl nucleus in a beta-imidated phenylhydrazine compound and subsequently hydrolyzing the chlorinated compound. Said chlorophenylhydrazine compound is useful as starting material for the production of herbicide, insecticide and photographic coupler is produced in high yield and low cost.

  本发明公开了一种氯苯肼化合物的生产工艺，该工艺包括对β-亚胺化苯肼化合物中苯基核上的至少一个氢原子进行氯化，然后对氯化化合物进行水解。所述氯苯肼化合物可用作生产除草剂、杀虫剂和感光耦合剂的起始原料，产量高且成本低。
• Anaerobically curable (meth)acrylate compositions
  申请人：Henkel IP & Holding GmbH

  公开号：US11111416B2

  公开（公告）日：2021-09-07

  Anaerobically curable (meth)acrylate compositions, methods for their preparation, and uses thereof. The anaerobically curable compositions proved effective at bonding a wide variety of substrates, and the tensile strength performance of said compositions is excellent.

  厌氧固化（甲基）丙烯酸酯组合物、制备方法及其用途。事实证明，厌氧固化组合物能有效粘合各种基材，而且拉伸强度性能优异。
• Michaelis; Hermens, Chemische Berichte, 1892, vol. 25, p. 2751
  作者：Michaelis、Hermens

  DOI：——

  日期：——
• Arndt; Loewe; Tarlan-Akoen, Istanbul Universitesi Fen Fakultesi Mecmuasi, Seri A: Matematik-Fizik-Kimya, 1948, vol. 13, p. 127
  作者：Arndt、Loewe、Tarlan-Akoen

  DOI：——

  日期：——