4-sec-butyl-2-nitro-acetanilide | 65439-19-2

• 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: 4-sec-butyl-2-nitro-acetanilide
• 英文别名: 2'-Nitro-4'-sec-butylacetanilide；4-sec.-Butyl-2-nitro-acetanilid；N-(4-butan-2-yl-2-nitrophenyl)acetamide
• CAS: 65439-19-2
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: GHWIIZNVHINFLV-UHFFFAOYSA-N

物化性质

• 熔点：
  15-17 °C
• 沸点：
  392.5±42.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-sec-butyl-2-nitro-acetanilide 在 盐酸 、 硫酸 、 sodium nitrite 作用下， 反应 1.0h， 生成 4-sec-butyl-2-nitrophenyl azide
  参考文献：
  名称：

  5-(4′-Substituted-2′-nitroanilino)-1,2,3-triazoles as new potential potassium channel activators. I

  摘要：

  By the hypothesised correlation with the large conductance Ca++-activated potassium channel (BKCa) openers NS 004 and NS 1619, bearing a benzimidazolone ring, a series of new 5-(4'-substituted-2'-nitroanilino)-1,2,3-triazoles were synthesised and tested on in vitro isolated vascular preparation. The compounds were prepared. starting from the appropriately substituted 2-nitro-phenylazides by 1,3-dipolar cycloaddition reaction to cyanoacetamide and following Dimroth isomerisation of the corresponding 1-arylsubstituted-5-amino-1,2,3-triazoles. The analogous 5-(4'-substituted-2'-amino-anilino)-1,2,3-triazoles were also prepared to assess the role of the nitro group in the pharmacophoric model. Almost all the nitro compounds showed a vasorelaxant activity on endothelium-denuded rat aortic rings with a potency comparable to that recorded for the reference compound NS 1619. Such a vasorelaxing activity was significantly reduced by the increase of the level of membrane depolarisation and by the potassium channel blocker 4-aminopyridine with a pharmacodynamic behaviour consistent with a potassium channel activation. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00180-x
• 作为产物：
  描述：

  (+/-)-4-sec-Butyl-acetanilid 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以72%的产率得到4-sec-butyl-2-nitro-acetanilide
  参考文献：
  名称：

  5-(4′-Substituted-2′-nitroanilino)-1,2,3-triazoles as new potential potassium channel activators. I

  摘要：

  By the hypothesised correlation with the large conductance Ca++-activated potassium channel (BKCa) openers NS 004 and NS 1619, bearing a benzimidazolone ring, a series of new 5-(4'-substituted-2'-nitroanilino)-1,2,3-triazoles were synthesised and tested on in vitro isolated vascular preparation. The compounds were prepared. starting from the appropriately substituted 2-nitro-phenylazides by 1,3-dipolar cycloaddition reaction to cyanoacetamide and following Dimroth isomerisation of the corresponding 1-arylsubstituted-5-amino-1,2,3-triazoles. The analogous 5-(4'-substituted-2'-amino-anilino)-1,2,3-triazoles were also prepared to assess the role of the nitro group in the pharmacophoric model. Almost all the nitro compounds showed a vasorelaxant activity on endothelium-denuded rat aortic rings with a potency comparable to that recorded for the reference compound NS 1619. Such a vasorelaxing activity was significantly reduced by the increase of the level of membrane depolarisation and by the potassium channel blocker 4-aminopyridine with a pharmacodynamic behaviour consistent with a potassium channel activation. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00180-x

文献信息

• EP0039367A4
  申请人：——

  公开号：EP0039367A4

  公开（公告）日：1982-07-12
• UV-ABSORBING COMPOUNDS AND PHOTOGRAPHIC ELEMENTS CONTAINING THEM
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：EP0039367A1

  公开（公告）日：1981-11-11
• US4323633A
  申请人：——

  公开号：US4323633A

  公开（公告）日：1982-04-06
• [EN] UV-ABSORBING COMPOUNDS AND PHOTOGRAPHIC ELEMENTS CONTAINING THEM
  申请人：——

  公开号：WO1981001473A1

  公开（公告）日：1981-05-28

  (EN) It is desirable to protect color photographic dye images from ultraviolet radiation which tends to cause dyes to fade. It has been the practice in the art to add materials into or above the silver halide emulsions which will absorb ultraviolet radiation but allow transmission of visible radiation. One of the best classes of compounds are the 2-(2'-hydroxyphenyl)-benzotriazoles. These materials absorb ultraviolet radiation well, but tend to have poor solubility, crystallize out of the coating solution and emulsion, and diffuse through the photographic element. A novel class of substituted 2-(2'-hydroxyphenyl)-benzotriazoles has been found to reduce many of these problems. (FR) Il est souhaitable de proteger les matieres colorantes des images photographiques en couleur des radiations ultraviolettes qui ont tendance a provoquer un affaiblissement de ces matieres colorantes. La pratique courante dans l'art est celle d'ajouter des materiaux a l'interieur ou a la surface des emulsions d'- halogenure d'argent qui absorbent la radiation ultraviolette mais permettent la transmission de la radiation visible. Une des meilleures classes de composes est representee par les 2- (2'-hydroxyphenyle)-benzotriazoles. Ces materiaux absorbent efficacement la radiation ultraviolette, mais ont tendance a presenter une faible solubilite ils se cristallisent a l'exterieur de la solution et de l'emulsion de revetement, et se diffusent au travers de l'element photographique. Une nouvelle classe de 2- (2'-hydroxyphenyle)-benzotriazoles substitues a ete decouverte pour limiter un nombre considerable de ces problemes.