butan-2-one-(4-nitro-phenylhydrazone) | 1017-79-4

• 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: butan-2-one-(4-nitro-phenylhydrazone)
• 英文别名: methyl ethyl ketone 4-nitrophenylhydrazone；4-nitrophenylhydrazone of 2-butanone；Butan-2-on-(4-nitro-phenylhydrazon)；Methylaethylketon-(4-nitro-phenylhydrazon)；Ethyl-methyl-keton-(4-nitro-phenylhydrazon)；Methyl-ethyl-keton-(4-nitro-phenylhydrazon)；2-Butanone, 2-(4-nitrophenyl)hydrazone；N-(butan-2-ylideneamino)-4-nitroaniline
• CAS: 1017-79-4
• 化学式: C₁₀H₁₃N₃O₂
• 分子量: 207.232
• InChiKey: HCKKWFJUSMCMHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  butan-2-one-(4-nitro-phenylhydrazone) 在 盐酸 、 sodium hydride 作用下， 反应 2.5h， 生成 1,2,3-trimethyl-5-nitroindole
  参考文献：
  名称：

  2,3-Dialkyl(dimethylamino)indoles: interaction with 5HT1, 5HT2, and rat stomach fundal serotonin receptors

  摘要：

  2,3-Dialkyl(dimethylamino)indoles, synthesized via the Fisher indole synthesis, were found to weakly bind to 5HT1 and 5HT2 sites in brain cortical membranes (IC50 greater than 1 microM at both sites for all compounds). These (dimethylamino)indoles were relatively potent antagonists of the serotonin receptor in the rat stomach fundus. At higher concentrations, several of the compounds were weak agonists at this receptor. For direct comparison with data obtained in the isolated rat fundus, antagonism of serotonin-induced contractions at 5HT2 receptors in the rat jugular vein was also examined. Several of the compounds showed good selectivity for the fundus receptor relative to the 5HT2 receptor; together with minimal affinity for 5HT1 and 5HT2 binding sites in brain cortical membranes, these results support the idea that the serotonin receptor in the stomach fundus is distinct from 5HT1 and 5HT2 binding sites.

  DOI：

  10.1021/jm00161a048
• 作为产物：
  描述：

  4-硝基苯胺 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 生成 butan-2-one-(4-nitro-phenylhydrazone)
  参考文献：
  名称：

  One-Pot Synthesis of Pyrrolo[3,2-f]- and Pyrrolo[2,3-h]quinoline Derivatives: Observation of an Unexpected Mechanistic Pathway

  摘要：

  从取代的5-氨基吲哚、苯甲醛和苯乙炔出发，以La(OTf)3作为催化剂，一锅合成了吡咯并[3,2-f]和吡咯并[2,3-h]喹啉，并取得了良好的产率。5-氨基吲哚中的吲哚结构被认为主要负责意外的机理路径，从而形成吡咯并[2,3-h]喹啉。

  DOI：

  10.1055/s-0031-1290565

文献信息

• 224. Addition reactions of the indole nucleus
  作者：S. G. P. Plant、M. L. Tomlinson

  DOI：10.1039/jr9330000955

  日期：——
• van Ekenstein; Blanksma, Recueil des Travaux Chimiques des Pays-Bas, 1903, vol. 22, p. 439
  作者：van Ekenstein、Blanksma

  DOI：——

  日期：——
• 621. Indoles. Part V. The Fischer cyclisation of some meta-substituted arylhydrazones
  作者：D. W. Ockenden、K. Schofield

  DOI：10.1039/jr9570003175

  日期：——
• Fast Alpha Nucleophiles: Structures that Undergo Rapid Hydrazone/Oxime Formation at Neutral pH
  作者：Eric T. Kool、Pete Crisalli、Ke Min Chan

  DOI：10.1021/ol500262y

  日期：2014.3.7

  Hydrazones and oximes are widely useful structures for conjugate formation in chemistry and biology, but their formation can be slow at neutral pH. Kinetics studies were performed for a range of structurally varied hydrazines, and a surprisingly large variation in reaction rate was observed. Structures that undergo especially rapid reactions were identified, enabling reaction rates that rival orthogonal cycloaddition-based conjugation chemistries.
• Butler, Richard N.; Morris, Gerard J., Journal of the Chemical Society. Perkin transactions I, 1980, p. 2218 - 2221
  作者：Butler, Richard N.、Morris, Gerard J.

  DOI：——

  日期：——