N-2-(3'-phthalide-yl)phthalazin-1-one | 55294-87-6

• 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: N-2-(3'-phthalide-yl)phthalazin-1-one
• 英文别名: N-2-(3'-phthalidyl)phthalazin-1-one；2-(3-oxo-1,3-dihydro-isobenzofuran-1-yl)-2H-phthalazin-1-one；2-phthalidyl-2H-phthalazin-1-one；2-Phthalidyl-2H-phthalazin-1-on；2-(3-Phthalidyl)phthalazin-1(2H)-on；2-Phthalidyl-1(2H)-phthalazinon；1(2H)-Phthalazinone, 2-(1,3-dihydro-3-oxo-1-isobenzofuranyl)-；2-(3-oxo-1H-2-benzofuran-1-yl)phthalazin-1-one
• CAS: 55294-87-6
• 化学式: C₁₆H₁₀N₂O₃
• 分子量: 278.267
• InChiKey: LZRPGFXKXJHZIR-UHFFFAOYSA-N

物化性质

• 熔点：
  225-226 °C(Solv: benzene (71-43-2))
• 沸点：
  525.3±60.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-2-(3'-phthalide-yl)phthalazin-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以73.2%的产率得到1-(2H)-酞嗪酮
  参考文献：
  名称：

  Synthesis and spectral study ofN-2-(3′-phthalidyl)phthalazin-1-one

  摘要：

  N-2-(3'-Phthalidyl)phthalazin-1-one was synthesized by the condensation of 2-carboxybenzaldehyde with hydrazine hydrate using polyphosphoric acid as catalyst and solvent. Its H-1 and C-13 NMR spectra were completely assigned utilizing the two-dimensional H-1-detected heteronuclear one-bond (HMQC) and multiple-bond (HMBC) techniques together with H-1-H-1 COSY and NOESY (homonuclear Overhauser and chemical exchange spectroscopy) correlation techniques. These techniques were also valuable in assigning the protons of its hydrazinolysis product, which were previously incompletely reported because of the overlap of proton signals. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1097-458x(199902)37:2<149::aid-mrc436>3.0.co;2-7
• 作为产物：
  描述：

  邻羧基苯甲醛 在 PPA 、 一水合肼 作用下， 反应 8.5h， 以50.4%的产率得到N-2-(3'-phthalide-yl)phthalazin-1-one
  参考文献：
  名称：

  Synthesis and spectral study ofN-2-(3′-phthalidyl)phthalazin-1-one

  摘要：

  N-2-(3'-Phthalidyl)phthalazin-1-one was synthesized by the condensation of 2-carboxybenzaldehyde with hydrazine hydrate using polyphosphoric acid as catalyst and solvent. Its H-1 and C-13 NMR spectra were completely assigned utilizing the two-dimensional H-1-detected heteronuclear one-bond (HMQC) and multiple-bond (HMBC) techniques together with H-1-H-1 COSY and NOESY (homonuclear Overhauser and chemical exchange spectroscopy) correlation techniques. These techniques were also valuable in assigning the protons of its hydrazinolysis product, which were previously incompletely reported because of the overlap of proton signals. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1097-458x(199902)37:2<149::aid-mrc436>3.0.co;2-7

文献信息

• Ultrasensitive fluorescent detection of nitroexplosives by dihydro-oxoisobenzofuranyl-phthalazinone engendered from Cd(II) catalyzed cyclization of azinodimethylidyne-benzoic acid
  作者：Durgesh Singh、Subhash Chandra、Rampal Pandey

  DOI：10.1039/d2nj06277a

  日期：——

  human safety. A Schiff base 2,2′-(azinodimethylidyne)-bis-benzoic acid (2) was synthesized, characterized, and cyclized to form 2-(1,3-dihydro-1-oxoisobenzofuran-3-yl)phthalazin-1(2H)-one (1) upon treatment with various transition and lanthanide metal ions, especially with Cd(II). Further, the cyclized product 1 could act as a nanomolar sensitive fluorescent ‘turn-off’ probe for 2-nitrophenol (o-NP

  通过可行、直接和有效的技术检测化学爆炸物对于人类安全至关重要。合成、表征和环化席夫碱 2,2'-(叠氮基二甲基亚炔)-双苯甲酸 ( 2 ) 形成 2-(1,3-二氢-1-oxoisobenzofuran-3-yl)phthalazin-1(2 H )-one ( 1 ) 经过各种过渡和镧系金属离子处理，尤其是 Cd( II )。此外，环化产物1可以作为2-硝基苯酚（ o -NP，86%）和苦味酸（PA，81%）的纳摩尔敏感荧光“关闭”探针，其中， 1的选择性更高PA 优于o -NP。的荧光猝灭1在 PA 和o -NP存在下可能归因于能量转移机制。o -NP 和 PA的结合常数约为 10 4 M -1，而斯特恩-沃尔默常数 ( K sv ) 估计约为 10 5。1对o -NP 和 PA的检测限 (LoD)分别确定为 4.52 ppb 和 6.81 ppb，而定量限 (LoQ) 在 DMF/H
• Griehl; Hecht, Chemische Berichte, 1958, vol. 91, p. 1816
  作者：Griehl、Hecht

  DOI：——

  日期：——
• US3886154A
  申请人：——

  公开号：US3886154A

  公开（公告）日：1975-05-27