4-chloro-5-(2-hydroxyethylamino)-2-methyl-3(2H)pyridazinone | 69152-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-chloro-5-(2-hydroxyethylamino)-2-methyl-3(2H)pyridazinone
• 英文别名: 4-chloro-5-(2-hydroxyetylamino)-2-methyl-3(2H)-pyridazinone；4-chloro-5-(N-2-hydroxyethylamino)-2-methyl-3(2H)-pyridazinone；4-Chlor-5-<2-hydroxy-aethylamino>-2-methyl-2H-pyridazin-3-on；4-chloro-5-(2-hydroxy-ethylamino)-2-methyl-2H-pyridazin-3-one；4-Chloro-5-(2-hydroxyethylamino)-2-methylpyridazin-3-one
• CAS: 69152-56-3
• 化学式: C₇H₁₀ClN₃O₂
• 分子量: 203.628
• InChiKey: XDEFFXSYYWYJNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-5-(2-hydroxyethylamino)-2-methyl-3(2H)pyridazinone 在 sodium sulfide 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 3,4-dihydro-7-methyl-2H-pyridazino<4,5-b>-1,4-thiazin-8(7H)-one
  参考文献：
  名称：

  Syntheses of 3,4-dihydro-2H-pyridazino(4,5-b)-1,4-thiazin-8(7H)-one and -5(6H)-one.

  摘要：

  合成了两种由1, 4-噻嗪和3(2H)-哒嗪酮组成的新型稠环体系。 4-氯-5-(2-氯乙氨基)分子内环化得到3, 4-二氢-7-甲基-2H-哒嗪基[4, 5-b]-1, 4-噻嗪-8(7H)-酮)-2-甲基-3(2H)-哒嗪酮与硫化钠。异构体3, 4-二氢-6-甲基-2H-哒嗪基-[4, 5-b]-1, 4-噻嗪-5(6H)-酮，直接由4, 5-二氯缩合得到-2-甲基-3(2H)-哒嗪酮与2-氨基乙硫醇钠。

  DOI：

  10.1248/cpb.30.1030
• 作为产物：
  描述：

  4,5-二氯-2-甲基哒嗪-3-酮 在 palladium on activated charcoal 环己烯 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-chloro-5-(2-hydroxyethylamino)-2-methyl-3(2H)pyridazinone
  参考文献：
  名称：

  Lipophilicity of Aminopyridazinone Regioisomers

  摘要：

  Ten pairs of pyridazinone regioisomers were prepared, and their lipophilicity was described by the logarithm of the octanol/water partition coefficient (log P) determined experimentally and calculated with prediction methods. The 4- and 5-(substituted amino)-3(2H)-pyridazinone regioisomers were synthesized by nucleophilic substitution of one of the chloro atoms of 4,5-dichloro-2-methyl-3(2H)pyridazinone or its 6-nitro derivative. Structures of new compounds were proven by spectroscopic methods. The experimental log P values were obtained by a shake flask method in octanol and a Sorensen buffer (pH 7.4) solvent system. A consequent difference was found in the lipophilicity of regioisomers. For each isomer pair, the log P value of the 4-isomer was significantly (average by 0.75 log unit) higher than that of the 5-isomer. Some quantum chemical calculations as well as X-ray analysis of two pairs of regioisomers were also carried out to gain insight into the structural differences of regioisomers. The log P values were calculated by the fragmental approach KOWWIN and a QSPR analysis (3DNET). The a priori KOWWIN gave poor agreement, but with the programs KOWWIN with EVA (experimental value adjusted) and 3DNET, the results were generally in agreement with experiment.

  DOI：

  10.1021/jf0343938

文献信息

• Synthesis and biological activity of pyridazinooxazines.
  作者：TOSHIYASU MATSUO、YOSHITSUGU TSUKAMOTO、TAKASHI TAKAGI、MAKOTO SATO

  DOI：10.1248/cpb.30.832

  日期：——

  4-Chloro-5-(2-hydroxyethylamino)-3 (2H)-pyridazinones were converted upon treatment with base to novel fused ring compounds, 3, 4-dihydro-2H-pyridazino [4, 5-b]-1, 4-oxazin-8 (7H)-ones. When a nitrogen atom in the hydroxyethylamino group or at the 2-position of the 3 (2H)-pyridazinone ring had a remaining hydrogen, the ring closure reaction did not occur. 3, 4-Dihydro-2H-pyridazino [4, 5-b]-1, 4-oxazine was similarly synthesized from corresponding precursor. The presence of a C-6 amino group in the precursor did not affect the ring formation mentioned above, but when the amino group was diazotized, ring formation took place in a different fashion, involving the C-6 diazonium moiety as a leaving group, to give another ring system, 6, 7-dihydro-2H-pyridazino [3, 4-b]-[1, 4] oxazin-3 (5H)-one. Similar phenomena were observed in the cases of precursors having a C-6 nitro group : cyclization occurred involving the elimination of the nitro group to give fused ring products. The method was applied to the formation of a tricyclic heterocycle, 2H-pyridazino [3, 4-b] [1, 4] benzoxazin-3 (5H)-one. Some compounds thus obtained were found to have potent analgesic and significant anti-inflammatory activities in animal models.

  4-氯-5-(2-羟基乙基氨基)-3 (2H)-吡嗪酮在碱处理后被转化为新型的融合环化合物，3, 4-二氢-2H-吡嗪[4, 5-b]-1, 4-氧杂啉-8 (7H)-酮。当羟基乙基氨基团中的氮原子或3 (2H)-吡嗪酮环的2位有剩余氢时，环闭合反应不会发生。3, 4-二氢-2H-吡嗪[4, 5-b]-1, 4-氧杂啉也通过相应前体合成。前体中的C-6氨基团对以上提到的环形成并没有影响，但当氨基团被重氮化时，环形成以不同的方式进行，涉及C-6重氮基团作为离去基团，形成另一个环系，6, 7-二氢-2H-吡嗪[3, 4-b]-[1, 4]氧杂啉-3 (5H)-酮。在C-6硝基基团的前体案例中也观察到了类似现象：环化发生，涉及硝基基团的消除，从而形成融合环产物。该方法被应用于三环杂环的形成，2H-吡嗪[3, 4-b][1, 4]苯氧杂啉-3 (5H)-酮。通过这种方法获得的一些化合物在动物模型中显示出强效的镇痛和显著的抗炎活性。
• MATSUO, TOSHIYASU;TSUKAMOTO, YOSHITSUGU;TAKAGI, TAKASHI;YAGINUMA, HIDEYA, CHEM. AND PHARM. BULL., 1982, 30, N 3, 1030-1032
  作者：MATSUO, TOSHIYASU、TSUKAMOTO, YOSHITSUGU、TAKAGI, TAKASHI、YAGINUMA, HIDEYA

  DOI：——

  日期：——
• MATSUO, TOSHIYASU;TSUKAMOTO, YOSHITSUGU;TAKAGI, TAKASHI;SATO, MAKOTO, CHEM. AND PHARM. BULL., 1982, 30, N 3, 832-842
  作者：MATSUO, TOSHIYASU、TSUKAMOTO, YOSHITSUGU、TAKAGI, TAKASHI、SATO, MAKOTO

  DOI：——

  日期：——