acetic acid-[4-(phenylhydrazono-methyl)-anilide] | 59670-41-6

• 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: acetic acid-[4-(phenylhydrazono-methyl)-anilide]
• 英文别名: 4-Acetamino-benzaldehyd-phenylhydrazon；Essigsaeure-[4-(phenylhydrazono-methyl)-anilid]；4-Acetylamino-benzaldehyd-phenylhydrazon；N-{4-[(E)-(2-phenylhydrazono)methyl]phenyl}acetamide；N-[4-[(E)-(phenylhydrazinylidene)methyl]phenyl]acetamide
• CAS: 59670-41-6
• 化学式: C₁₅H₁₅N₃O
• 分子量: 253.304
• InChiKey: MITYRPOKQBVKMJ-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  acetic acid-[4-(phenylhydrazono-methyl)-anilide] 在 盐酸 、 甲醇 、 亚硝酸异戊酯 作用下， 生成 5-(4-amino-phenyl)-2,3-diphenyl-tetrazolium; chloride
  参考文献：
  名称：

  Ashley et al., Journal of the Chemical Society, 1953, p. 3881,3885,3886

  摘要：

  DOI：
• 作为产物：
  描述：

  对乙酰氨基苯甲醛 、 苯肼 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 acetic acid-[4-(phenylhydrazono-methyl)-anilide]
  参考文献：
  名称：

  Aminyl and iminyl radicals from arylhydrazones in the photo-induced DNA cleavage

  摘要：

  Photolytic cleavage of the nitrogen-nitrogen single bond in benzaldehyde phenylhydrazones produced aminyl (R2N) and iminyl (R2C=N) radicals. This photochemical property was utilized in the development of hydrazones as photo-induced DNA-cleaving agents. Irradiation with 350 nm UV light of arylhydrazones bearing substituents of various types in a phosphate buffer solution containing the supercoiled circular phiX174 RFI DNA at pH 6.0 resulted in single-strand cleavage of DNA. Attachment of the electron-donating OMe group to arylhydrazones increased their DNA-cleaving activity. Results from systematic studies indicate that both the aminyl and the iminyl radicals possessed DNA-cleaving ability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.037

文献信息

• Syntheses of Formazans Under Phase-Transfer Conditions
  作者：Alan A. Katritzky、Sergei A. Belyakov、Dai Cheng、H. Dupont Durst

  DOI：10.1055/s-1995-3958

  日期：1995.5

  Several 1,3,5-triarylformazans were synthesized (42-77%) using a new methodology. Azo-coupling of aryldiazonium salts with arylaldehyde arylhydrazones under mild basic conditions in two-phase liquid-liquid media is efficiently promoted by phase-transfer catalysts (onium salts or dicyclohexano-18-crown-6) at 5-25°C. The condensation of benzaldehyde with phenylhydrazine followed by phase-transfer catalyzed azo-coupling with phenyldiazonium chloride (one-pot procedure) gave 1,3,5-triphenylformazan in a 54% yield without isolation of the intermediate benzaldehyde phenylhydrazone. A double azo-coupling reaction of phenyldiazonium chloride with 9 different CH-active compounds afforded corresponding formazan only in the case of phenylpyruvic acid. Reaction in malonamide gave 3-carbamoyl-1,5-diphenylformazan instead of the expected 1,5-diphenylformazan.

  采用一种新方法合成了多种 1,3,5-三芳基甲臢（42-77%）。相转移催化剂（鎓盐或二环己烷-18-冠醚-6）可在 5-25°C 的温度下，在两相液液介质的温和碱性条件下有效促进芳基偶氮盐与芳基醛芳基肼的偶氮偶联反应。苯甲醛与苯肼发生缩合反应，然后在相转移催化下与苯基重氮氯化物发生偶氮偶联反应（一锅法），得到 1,3,5-三苯基甲酰肼，收率为 54%，且无需分离中间体苯甲醛苯腙。苯基重氮酰氯与 9 种不同的 CH 活性化合物进行双偶氮偶联反应，只有苯基丙酮酸能得到相应的甲臢。在丙二酰胺中反应得到的是 3-氨基甲酰基-1,5-二苯基甲臢，而不是预期的 1,5-二苯基甲臢。
• Cohn; Springer, Monatshefte fur Chemie, 1903, vol. 24, p. 91
  作者：Cohn、Springer

  DOI：——

  日期：——
• Katritzky Alan R., Belyakov Sergei A., Cheng Dai, Durst H. Dupont, Synthesis, (1995) N 5, S 577-581
  作者：Katritzky Alan R., Belyakov Sergei A., Cheng Dai, Durst H. Dupont

  DOI：——

  日期：——
• Ashley et al., Journal of the Chemical Society, 1953, p. 3881,3885,3886
  作者：Ashley et al.

  DOI：——

  日期：——
• Aminyl and iminyl radicals from arylhydrazones in the photo-induced DNA cleavage
  作者：Jih Ru Hwu、Chun Chieh Lin、Shih Hsien Chuang、Ke Yung King、Tzu-Rong Su、Shwu-Chen Tsay

  DOI：10.1016/j.bmc.2004.03.037

  日期：2004.5

  Photolytic cleavage of the nitrogen-nitrogen single bond in benzaldehyde phenylhydrazones produced aminyl (R2N) and iminyl (R2C=N) radicals. This photochemical property was utilized in the development of hydrazones as photo-induced DNA-cleaving agents. Irradiation with 350 nm UV light of arylhydrazones bearing substituents of various types in a phosphate buffer solution containing the supercoiled circular phiX174 RFI DNA at pH 6.0 resulted in single-strand cleavage of DNA. Attachment of the electron-donating OMe group to arylhydrazones increased their DNA-cleaving activity. Results from systematic studies indicate that both the aminyl and the iminyl radicals possessed DNA-cleaving ability. (C) 2004 Elsevier Ltd. All rights reserved.