N-benzoyl-benzamidrazone | 4057-68-5

• 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: N-benzoyl-benzamidrazone
• 英文别名: N-Benzoyl-benzamidrazon；N-(α-Amino-benzal)-N'-benzoyl-hydrazin；N-(α-Imino-benzyl)-N'-benzoyl-hydrazin；N²-Benzoyl-benzhydrazid-imid；Phenyl-N¹-benzoyl-amidrazon；N-[(Z)-[amino(phenyl)methylidene]amino]benzamide
• CAS: 4057-68-5
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: HFXWIIMKXOPWPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  N-benzoyl-benzamidrazone 以 甲苯 为溶剂， 反应 48.0h， 以97%的产率得到3,5-二(苯基)-1H-1,2,4-三唑
  参考文献：
  名称：

  C-(β-d-Glucopyranosyl)formamidrazones, formic acid hydrazides and their transformations into 3-(β-d-glucopyranosyl)-5-substituted-1,2,4-triazoles: a synthetic and computational study

  摘要：

  Synthesis of O-perbenzoylated 3-(beta-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, precursors of potent inhibitors of glycogen phosphorylase, was studied by ring closures of N-1-acyl-carboxamidrazone type intermediates. Reactions of C-(beta-D-glucopyranosyl)formimidate or C-(beta-D-glucopyranosyl)formamidine with acid hydrazides as well as acylation of C-(beta-D-glucopyranosyl)formamidrazone by acid chlorides unexpectedly gave the corresponding 1,3,4-oxadiazoles instead of 1,2,4-triazoles. The desired triazoles were obtained in reactions of C-(beta-D-glucopyranosyl)formamidine or C-(beta-D-glucopyranosyl) formyl chloride with arenecarboxamidrazones, and also in acylations of N-1-tosyl-C-(beta-D-glucopyranosyl)formamidrazone with acid chlorides. Theoretical calculations (B3LYP and M06-2X OFT with the standard 6-31G(d,p) basis set) on simple model compounds with methyl and phenyl substituents to understand the bifurcation of the ring closure of N-1-acyl-carboxamidrazones indicated that in general the reaction led to 1,2,4-triazoles. However, the probability of the 1,3,4-oxadiazole forming pathway was shown to be significantly higher with N-1-benzoyl-acetamidrazones, which were closest analogues of the intermediates resulting in C-glucosyl-1,3,4-oxadiazoles. It was thereby demonstrated that the substitution pattern of the N-1-acyl-carboxamidrazones played a fundamental role in determining the direction of the ring closing reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.099
• 作为产物：
  描述：

  苯甲亚胺酸乙酯 在 sodium hydroxide 、 一水合肼 作用下， 生成 N-benzoyl-benzamidrazone
  参考文献：
  名称：

  Pinner, Chemische Berichte, 1894, vol. 27, p. 1007

  摘要：

  DOI：

文献信息

• Pinner, Justus Liebigs Annalen der Chemie, 1897, vol. 297, p. 252,293
  作者：Pinner

  DOI：——

  日期：——
• A new class of nonhormonal pregnancy-terminating agents. Synthesis and contragestational activity of 3,5-diaryl-s-triazoles
  作者：Amedeo Omodei-Sale、Pietro Consonni、Giulio Galliani

  DOI：10.1021/jm00362a018

  日期：1983.8

  A series of 3,5-diaryl-s-triazoles were synthesized and evaluated as postimplantation contragestational agents. The introduction of various substituents (e.g., an o-alkyl chain on one phenyl and a m-alkoxy group on the other) was found to increase the potency. Several compounds with very high pregnancy-terminating activity in both hamsters and rats were obtained. One of these, 3-(2-ethylphenyl)-5-(3-methoxyphenyl)-s-triazole, DL 111 (36), was selected for detailed evaluation in various animal species. A synthetic scheme for the preparation of these compounds and preliminary structure-activity relationships are presented.
• Postowskii; Wereschtschagina, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2139,2141,2142;engl.Ausg.S.2105,2107,2108
  作者：Postowskii、Wereschtschagina

  DOI：——

  日期：——
• Becker,H.G.O. et al., Journal fur praktische Chemie (Leipzig 1954), 1970, vol. 312, p. 610 - 621
  作者：Becker,H.G.O. et al.

  DOI：——

  日期：——
• Eilingsfeld,H., Chemische Berichte, 1965, vol. 98, p. 1308 - 1321
  作者：Eilingsfeld,H.

  DOI：——

  日期：——