1,2-dihydro-2-(4,5-dihydroimidazol-2-yl)phthalazin-1-ol | 183283-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1,2-dihydro-2-(4,5-dihydroimidazol-2-yl)phthalazin-1-ol
• 英文别名: 2-(4,5-dihydro-1H-imidazol-2-yl)-1H-phthalazin-1-ol
• CAS: 183283-10-5
• 化学式: C₁₁H₁₂N₄O
• 分子量: 216.242
• InChiKey: DLNCWBWQAODXQC-UHFFFAOYSA-N

物化性质

• 沸点：
  394.3±52.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  60.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-2-(4,5-dihydroimidazol-2-yl)phthalazin-1-ol 在 盐酸 、 甲醇 、 sodium hydroxide 作用下， 反应 48.0h， 生成 (4aSR,15bRS,15cRS)-1,2,3,4,6,7,15b,15c-octahydro-4aH-imidazo[1,2-a]phthalazino[2,1-c]quinazolin-4a-ol
  参考文献：
  名称：

  Acid Assisted Reactions of 1,2-Dihydro-2-(4,5-dihydroimidazol-2-yl)phthalazin-1-ol with Aryl(Heteroaryl) Methyl Ketones

  摘要：

  A series of the 1-[2-(4,5-dihydro-1H-imidazol-2-yl)-1,2-dihydro-phthalazin-1-yl]-2-arylethanone hydrochlorides (2a-i) was synthesized by acid assisted reaction of phthalazine pseudobase (1) with aryl(heteroaryl) methyl ketones. A similar reactions of 1 with cyclohexanone and benzo-1,4-dioxan-2-one afforded 1, 2, 3, 4, 6, 7, 15b, 15c-octahydro-4aH-imidazo[1,2-a]phthalazino[2,1-c]quinazolin-4a-ol (5) and 7-[2-(4,5-dihydro-1H-imidazol-2-yl)-1,2-dihydro-phthalazin-1-yl]-1,4-benzodioxin-2(3H)-one (6), respectively. Structures of these compounds were confirmed by IR and NMR spectroscopy as well as X-Ray crystallographic analysis of the free base (3a). Biological activity of the compounds (2) was examined on rabbit aortic rings.

  DOI：

  10.3987/com-02-9671
• 作为产物：
  描述：

  2,3-二氮杂萘 、 2-氯-4,5-二氢-1H-咪唑磺酸盐 在 sodium hydroxide 作用下， 以39%的产率得到1,2-dihydro-2-(4,5-dihydroimidazol-2-yl)phthalazin-1-ol
  参考文献：
  名称：

  2-氯-4,5-二氢咪唑，8.通过1,2-二氢-2-（4,5-二氢咪唑-2-基）酞嗪-1-醇与活性亚甲基化合物的反应合成新颖的稠合杂环系统†

  摘要：

  1与哒嗪或酞嗪的三组分反应分别得到1,2-二氢衍生物2a和2b。在NaOH水溶液中进行的1与酞嗪的相似反应导致假碱3的形成。通过与多种活性亚甲基化合物反应，后一种化合物被证明是制备一系列新型1,2-二氢酞嗪衍生物4a–c，5和6a–b的极佳底物。

  DOI：

  10.1002/jlac.199619961028

文献信息

• Synthesis and structure of novel 1,2-dihydro-phthalazine containing betaines
  作者：Franciszek Saczewski、Maria Gdaniec

  DOI：10.1002/jhet.5570350333

  日期：1998.5

  5-dihydro-1H-imidazol-3-iurn-2-yl)-1,2-dihydro-1-phthalazin]-1,4-dialkoxy-1,4-dioxo-2-buten-2-olates 7 and 8. Enolic ester compounds underwent further transesterification reactions with formation of the betaines 9 and 10. The unequivocal structural assignement of these compounds was achieved by spectroscopic 1H and 13C nmr methods as well as X-ray analysis of 7.

  1,2-二氢-2-（4,5-二氢咪唑-2-基）酞嗪-1-醇1与乙炔二羧酸二烷基酯放热反应，生成3- [2-（4,5-二氢-1 H-咪唑-3-iurn -2-基）-1，2-二氢-1-酞嗪] -1，4-二烷氧基-1，4-二氧代-2-丁烯-2-酸酯7和8。烯醇酯化合物进行进一步的酯交换反应，形成甜菜碱9和10。这些化合物的明确结构分配是通过1 H和13 C nmr光谱方法以及7的X射线分析实现的。
• 2-Chloro-4,5-dihydroimidazole, 8. Syntheses of Novel Fused Heterocyclic Systems by Reactions of 1,2-Dihydro-2-(4,5-dihydroimidazol-2-yl)phthalazin-1-ol with Active Methylene Compounds
  作者：Franciszek Saczewski、Maria Gdaniec

  DOI：10.1002/jlac.199619961028

  日期：1996.10

  Three-component reactions of 1 with pyridazine or phthalazine afforded the 1,2-dihydro derivatives 2a and 2b, respectively. A similar reaction of 1 with phthalazine performed in aqueous NaOH led to the formation of pseudobase 3. The latter compound proved to be an excellent substrate for the preparation of a series of novel 1,2-dihydrophthalazine derivatives 4a–c, 5 as well as 6a–b by reactions with a variety

  1与哒嗪或酞嗪的三组分反应分别得到1,2-二氢衍生物2a和2b。在NaOH水溶液中进行的1与酞嗪的相似反应导致假碱3的形成。通过与多种活性亚甲基化合物反应，后一种化合物被证明是制备一系列新型1,2-二氢酞嗪衍生物4a–c，5和6a–b的极佳底物。
• Acid Assisted Reactions of 1,2-Dihydro-2-(4,5-dihydroimidazol-2-yl)phthalazin-1-ol with Aryl(Heteroaryl) Methyl Ketones
  作者：Franciszek Saczewski、Ewa Kobierska、Jacek Petrusewicz、Anna Gendzwill、Maria Gdaniec

  DOI：10.3987/com-02-9671

  日期：——

  A series of the 1-[2-(4,5-dihydro-1H-imidazol-2-yl)-1,2-dihydro-phthalazin-1-yl]-2-arylethanone hydrochlorides (2a-i) was synthesized by acid assisted reaction of phthalazine pseudobase (1) with aryl(heteroaryl) methyl ketones. A similar reactions of 1 with cyclohexanone and benzo-1,4-dioxan-2-one afforded 1, 2, 3, 4, 6, 7, 15b, 15c-octahydro-4aH-imidazo[1,2-a]phthalazino[2,1-c]quinazolin-4a-ol (5) and 7-[2-(4,5-dihydro-1H-imidazol-2-yl)-1,2-dihydro-phthalazin-1-yl]-1,4-benzodioxin-2(3H)-one (6), respectively. Structures of these compounds were confirmed by IR and NMR spectroscopy as well as X-Ray crystallographic analysis of the free base (3a). Biological activity of the compounds (2) was examined on rabbit aortic rings.