1-hydroxy-2-phenyl-pyrro<3,4-b>pyridine-3(1H)-one | 122706-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 1-hydroxy-2-phenyl-pyrro<3,4-b>pyridine-3(1H)-one
• 英文别名: 5,6-dihydro-5-hydroxy-6-phenyl-7H-pyrrolo<3,4-b>pyridin-7-one；6,7-dihydro-5-hydroxy-6-phenyl-5H-pyrrolo<3,4-b>pyridin-7-one；5-hydroxy-6-phenyl-5H-pyrrolo[3,4-b]pyridin-7-one；5,6-dihydro-5-hydroxy-6-phenyl-7H-pyrrolo[3,4-b]pyridin-7-one；7H-Pyrrolo[3,4-b]pyridin-7-one, 5,6-dihydro-5-hydroxy-6-phenyl-
• CAS: 122706-49-4
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: CBLVQROEGOSBJR-UHFFFAOYSA-N

物化性质

• 熔点：
  236-238 °C(Solv: methanol (67-56-1))
• 沸点：
  446.4±45.0 °C(Predicted)
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-hydroxy-2-phenyl-pyrro<3,4-b>pyridine-3(1H)-one 在 盐酸 、 钾硼氢 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 呋喃并[3,4-b]吡啶-5(7H)-酮
  参考文献：
  名称：

  Application of Organolithium and Related Reagents in Synthesis. XV. A Concise Regiospecific Conversion of Picolinic- and Isonicotinic Acids into 2-Benzoyl- and 4-Benzoylnicotinic Acids

  摘要：

  The synthesis of the azaphthalides (7) and (8) and their conversion into the corresponding 2- and 4-benzoyl-3-hydroxymethylpyridines (9) and (10), very useful precursors of the 2- and 4-benzoylated nicotinic acids (11) and (12), as a way of regiospecific transformation of the picolin- and isonicotinanilides (1) and (2) into nicotinic acid derivatives, is described.

  DOI：

  10.1080/00397919408010186
• 作为产物：
  描述：

  2,3-吡啶二羧酸酐 在 sodium tetrahydroborate 、 乙酸酐 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 1-hydroxy-2-phenyl-pyrro<3,4-b>pyridine-3(1H)-one
  参考文献：
  名称：

  Hitchings, Gregory J.; Vernon, John M., Journal of the Chemical Society. Perkin transactions I, 1990, # 6, p. 1757 - 1763

  摘要：

  DOI：

文献信息

• Antihypertensive benzopyran derivatives
  申请人：American Home Products Corporation

  公开号：US04983612A1

  公开（公告）日：1991-01-08

  Disclosed herein are novel benzopyrans having pharmacological activity, to a process for preparing them, to pharmaceutical compositions containing them, and to their use in the treatment of hypertension.

  本文披露了具有药理活性的新型苯并吡喃化合物，以及用于制备它们的方法，含有它们的药物组合物，以及它们在治疗高血压中的用途。
• Magnesium Ion Assisted Highly Regio- and Chemoselective Reduction of 5<i>H</i>-Pyrrolo[3,4-<i>b</i>]pyridine-5,7(6<i>H</i>)-diones with Sodium Borohydride. A Convenient Synthesis of 6,7-Dihydro-7-hydroxy-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-ones
  作者：Takehiko Goto、Michio Konno、Minoru Saito、Ryu Sato

  DOI：10.1246/bcsj.62.1205

  日期：1989.4.15

  were predominantly obtained in excellent yield by the reduction of the corresponding 5,7-diones with sodium borohydride in the presence of Mg ion at 0 °C. The highly regioselective production of the 7-hydroxy lactam in preference to the 5-hydroxy isomer was reasonably interpreted in terms of a chelate complex formation between the dione and Mg ion. The regioisomeric assignment was achieved by the transformation

  通过用硼氢化钠还原相应的 5,7-二酮，6-取代和未取代的 6,7-二氢-7-羟基-5H-吡咯并[3,4-b]吡啶-5-酮主要以优异的收率获得在 0 °C 存在 Mg 离子的情况下。7-羟基内酰胺优先于 5-羟基异构体的高度区域选择性生产被合理地解释为二酮和镁离子之间的螯合物形成。通过将 7-羟基内酰胺转化为 2-(羟甲基)-3-吡啶甲酰胺，可将其转化为已知的氮杂苯酞、呋喃 [3,4-b] 吡啶-5(7H)-酮，从而实现区域异构分配。此外，发现在低于 0 °C 时仍保持高化学选择性，只得到部分还原产物羟基内酰胺。
• Application of Organolithium and Related Reagents in Synthesis; Part 17: Synthesis of Azaisoindolo[2,1-a]quinoline Derivatives
  作者：Jan Epsztajn、Renata Grzelak、Andrzej Jóźwiak

  DOI：10.1055/s-1996-4366

  日期：1996.10

  The synthesis of the 3-hydroxy-5(or 7)-azaisoindolin-1-ones and their conversion into 2-aryl-2,3-dihydro-3-oxo-1H-azaisoindole-1-acetic acids, and their subsequent cyclization via sequential treatment with oxalyl chloride and aluminium chloride as a way of regiospecific transformation of pyridinecarboxylic acids into the corresponding dihydroazaisoindolo[2,1-a]quinolinediones is described.

  本文描述了3-羟基-5（或7）-氮杂异吲哚-1-酮的合成及其转化为2-芳基-2,3-二氢-3-氧-1H-氮杂异吲哚-1-乙酸，以及通过依次处理草酰氯和氯化铝实现的环化，作为将吡啶羧酸区域特异性转化为相应的二氢氮杂异吲哚[2,1-a]喹啉二酮的一种方法。
• Synthesis and Pharmacological Evaluation of<i>N</i>-(Dimethylamino)ethyl Derivatives of Benzo- and Pyridopyridazinones
  作者：Wanda Pakulska、Zbigniew Malinowski、Aleksandra K. Szczesniak、Elzbieta Czarnecka、Jan Epsztajn

  DOI：10.1002/ardp.200800016

  日期：2009.1

  New N‐(dimethylamino)ethyl derivatives of phthalazinones and pyridopyridazinones 7, 9 were synthesized and assayed as potential analgesic agents in the hot‐plate, tail‐flick, and writhing tests. Pharmacological assay demonstrated that eight (in ten) of the newly synthesized compounds showed antinociceptive activity. Especially, 2‐[2‐(dimethylamino)ethyl]‐4‐phenyl‐2H‐phthalazin‐1‐one 7a showed remarkably

  合成了酞嗪酮和吡啶并哒嗪酮 7、9 的新型 N-（二甲氨基）乙基衍生物，并在热板、甩尾和扭体试验中作为潜在的镇痛剂进行了分析。药理学分析表明，新合成的化合物中有八种（十分之八）显示出镇痛活性。特别是，2-[2-(二甲氨基)乙基]-4-苯基-2H-酞嗪-1-one 7a在所有测试中都显示出显着更高的镇痛活性。这与对脊柱上、脊柱和外周结构的影响有关。热板对疼痛刺激的敏感性下降高于安乃近。
• Synthesis of Some Novel <i>N</i>-Substituted Phthalazinone and Pyridopyridazinone Derivatives
  作者：Zbigniew Malinowski、Dariusz Sroczyński、Aleksandra K. Szcześniak

  DOI：10.1080/00397911.2015.1025282

  日期：2015.8.3

  Abstract Phthalazinone and pyridopyridazinone derivatives 3, 5, and 9 were prepared via reaction ofappropriate lactams 2 and 8 with 2-bromoethylphthalimide, N-tosylaziridine, and N,O-ditosyl derivatives of N-methylethanolamine in a two-step process in the presence of MeONa/MeOH or NaH/dimethylformamide (DMF). Starting compounds 2 and 8 were obtained by reaction of hydrazine hydrate with isoindolinones

  摘要 通过合适的内酰胺 2 和 8 与 2-溴乙基邻苯二甲酰亚胺、N-甲苯磺酰氮丙啶和 N-甲基乙醇胺的 N,O-二甲苯磺酰衍生物在两步法存在下反应制备了酞嗪酮和吡啶并哒嗪酮衍生物 3、5、9。 MeONa/MeOH 或 NaH/二甲基甲酰胺 (DMF)。通过水合肼与异吲哚酮1或氮杂异吲哚酮6反应得到起始化合物2和8。选择的N-(2-邻苯二甲酰亚胺乙基)-酞嗪酮通过处理以令人满意的收率转化为相应的2-[2-(甲氨基)乙基]-衍生物用肼。图形概要