2-[(2-oxo-1-phenylhydrazonopropan-1-yl)amino]benzoic acid | 60942-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(2-oxo-1-phenylhydrazonopropan-1-yl)amino]benzoic acid
• 英文别名: 2-[[2-Oxo-1-(2-phenylhydrazinyl)propylidene]amino]benzoic acid
• CAS: 60942-98-5
• 化学式: C₁₆H₁₅N₃O₃
• 分子量: 297.313
• InChiKey: MPOUXTSASZPLOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  90.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(2-oxo-1-phenylhydrazonopropan-1-yl)amino]benzoic acid 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到2-acetyl-4-phenyl-1,4-dihydro-1H-1,3,4-benzotriazepin-5-one
  参考文献：
  名称：

  Facile synthesis of model 1,4‐dihydro‐1 H ‐1,3,4‐benzotriazepin‐5‐ones

  摘要：

  Abstract2‐Aminobenzoic acid reacts readily, in the presence of triethylamine, with hydrazonoyl chlorides (5a‐c) (precursors of the reactive nitrile imine 1,3‐dipolar species) to afford high yields of the corresponding acyclic amidrazone adducts (6a‐c). The latter adducts undergo, in THF in presence of 1,1‐carbonyldiimida‐zole, smooth intramolecular cyclization involving the activated carboxyl and the NH‐ termini to deliver unequivocally the respective dihydro‐1,3,4‐benzotriazepin‐5‐ones (7a‐c).

  DOI：

  10.1002/jhet.5570390508
• 作为产物：
  描述：

  邻氨基苯甲酸 、 1-氯-1-(2-苯基亚肼基)乙酮 在 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以82%的产率得到2-[(2-oxo-1-phenylhydrazonopropan-1-yl)amino]benzoic acid
  参考文献：
  名称：

  Facile synthesis of model 1,4‐dihydro‐1 H ‐1,3,4‐benzotriazepin‐5‐ones

  摘要：

  Abstract2‐Aminobenzoic acid reacts readily, in the presence of triethylamine, with hydrazonoyl chlorides (5a‐c) (precursors of the reactive nitrile imine 1,3‐dipolar species) to afford high yields of the corresponding acyclic amidrazone adducts (6a‐c). The latter adducts undergo, in THF in presence of 1,1‐carbonyldiimida‐zole, smooth intramolecular cyclization involving the activated carboxyl and the NH‐ termini to deliver unequivocally the respective dihydro‐1,3,4‐benzotriazepin‐5‐ones (7a‐c).

  DOI：

  10.1002/jhet.5570390508

文献信息

• TRIMARCO P.; LASTRUCCI C., J. HETEROCYCL. CHEM. <JHTC-AD>, 1976, 13, NO 4, 913-915
  作者：TRIMARCO P.、 LASTRUCCI C.

  DOI：——

  日期：——
• Tautomerism and X-Ray Structure of Dihydro-5H-1,3,4-benzotriazepin- 5-ones
  作者：Mustafa M. El-Abadelah、Jalal A. Zahra、Bassam A. Abu Thaher、Martti Klinga

  DOI：10.3987/com-02-9587

  日期：——
• Facile synthesis of model 1,4‐dihydro‐1 <i>H</i> ‐1,3,4‐benzotriazepin‐5‐ones
  作者：Bassam A. Abu Thaher、Jalal A. Zahra、Mustafa M. El‐Abadelah

  DOI：10.1002/jhet.5570390508

  日期：2002.9

  Abstract2‐Aminobenzoic acid reacts readily, in the presence of triethylamine, with hydrazonoyl chlorides (5a‐c) (precursors of the reactive nitrile imine 1,3‐dipolar species) to afford high yields of the corresponding acyclic amidrazone adducts (6a‐c). The latter adducts undergo, in THF in presence of 1,1‐carbonyldiimida‐zole, smooth intramolecular cyclization involving the activated carboxyl and the NH‐ termini to deliver unequivocally the respective dihydro‐1,3,4‐benzotriazepin‐5‐ones (7a‐c).