3-(diethylamino)-4-nitroacetanilide | 88413-23-4

• 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: 3-(diethylamino)-4-nitroacetanilide
• 英文别名: n,n-Diethyl-2-nitro-5-acetaminoaniline；N-[3-(diethylamino)-4-nitrophenyl]acetamide
• CAS: 88413-23-4
• 化学式: C₁₂H₁₇N₃O₃
• 分子量: 251.285
• InChiKey: DLTNOXZLMDQCLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(diethylamino)-4-nitroacetanilide 在 吡啶 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 N-<3-(diethylamino)-4-nitrophenyl>methanesulfonamide
  参考文献：
  名称：

  Potential antitumor agents. 41. Analogs of amsacrine with electron-donor substituents in the anilino ring

  摘要：

  The preparation and antitumor activity of a series of 3'-alkylamino and 3'-dialkylamino analogues of amsacrine are reported. The results support previous work suggesting that the presence of electron-donating groups in the 3'-position of the anilino ring substantially enhance the antitumor activity of amsacrine analogues, possibly by the provision of high levels of electron density at the 6'-position. The alkylamino derivatives generally possess tighter DNA binding, higher levels of in vitro and in vivo antileukemic activity, and greater aqueous solubility than the corresponding amsacrine analogues.

  DOI：

  10.1021/jm00369a022
• 作为产物：
  描述：

  3-chloro-4-nitroacetanilide 、 二乙胺 生成 3-(diethylamino)-4-nitroacetanilide
  参考文献：
  名称：

  生物应用中偶氮苯光开关的光谱调谐

  摘要：

  通过将2,2'-氨基烷基取代基引入4,4'-二酰胺基取代的偶氮苯中，可以获得更长的转换波长，顺式异构体在还原性水环境中的良好光化学产率和稳定性。因此，该产品适用于细胞内环境中的生物分子结构的光控，例如在两种肽构型之间切换（参见图片）。

  DOI：

  10.1002/anie.200805013

文献信息

• DYES
  申请人：——

  公开号：US20010052156A1

  公开（公告）日：2001-12-20

  A colorant for coloring keratin fibers wherein the colorant contains a substantive dye which is a 4-nitroaniline derivative corresponding to formula (I): 1 in which R 1 , R 2 , R 3 and R 4 independently of one another represent a hydrogen atom, an alkyl, hydroxyalkyl, alkoxyalkyl, carbamyl alkyl, mesylaminoalkyl, acetylaminoalkyl, ureidoalkyl, carbalkoxyaminoalkyl, sulfalkyl, piperidinoalkyl, morpholinoalkyl or phenyl radical optionally substituted by an amino group in the para position, the alkyl or alkoxy groups containing 1 to 4 carbon atoms, with the proviso that the four substituents R 1 , R 2 , R 3 and R 4 do not simultaneously represent hydrogen, and the groups —NR 1 R 2 and —NR 3 R 4 may also represent an aziridine, acetidine, pyrrolidine, piperidine, azepan, azocine, morpholine, thiomorpholine or piperazine ring which may also bear another substituent R 8 at the nitrogen atom, R 8 being a hydrogen atom, a (C 1-4 )-alkyl, hydroxy-(C 2-3 )-alkyl, (C 1-4 )-alkoxy-(C 2-3 )-alkyl, amino-(C 2-3 )-alkyl or 2,3-dihydroxypropyl group, and R 5 , R 6 and R 7 independently of one another represent ahydrogen atom, a halogen atom, a (C 1-4 )-alkyl, (C 1-4 )-alkoxy, carboxy, sulfo or (C 2-4 )-hydroxyalkyl group, or a physiologically compatible salt of the compounds with an inorganic or organic acid.

  一种用于给角蛋白纤维着色的着色剂，其中该着色剂含有一种实质性染料，该染料是与式(I)相对应的4-硝基苯胺衍生物，式中R1、R2、R3和R4分别独立地代表氢原子、烷基、羟基烷基、烷氧基烷基、氨基甲酰基烷基、甲磺基氨基烷基、乙酰氨基烷基、脲基烷基、羰基氨基烷基、磺基烷基、哌啶基烷基、吗啉基烷基或苯基基团，该苯基基团在对位可能被氨基取代，烷基或烷氧基基团含有1至4个碳原子，但R1、R2、R3和R4的四个取代基不能同时代表氢，而基团—NR1R2和—NR3R4也可以表示一个氮杂环丙烷、乙酸丙烷、吡咯烷、哌啶、氮丙烷、氮环己烷、吗啉、硫吗啉或哌嗪环，该环也可以在氮原子处带有另一个取代基R8，R8为氢原子、(C1-4)-烷基、羟基-(C2-3)-烷基、(C1-4)-烷氧基-(C2-3)-烷基、氨基-(C2-3)-烷基或2,3-二羟基丙基基团，而R5、R6和R7分别独立地代表氢原子、卤原子、(C1-4)-烷基、(C1-4)-烷氧基、羧基、磺酸基或(C2-4)-羟基烷基，或者是与无机或有机酸形成的生理相容盐。
• OXIDATION DYES
  申请人：Andreas J. Bittner

  公开号：US20010005914A1

  公开（公告）日：2001-07-05

  The invention relates to oxidation colorants which are particularly suitable for coloring keratin fiber and to a method of coloring such fiber. The colorants contain as the preliminary oxidation dye at least one diamino aniline of the general formula (I), in which R 1 to R 6 independently of each other are hydrogen, a (C 1- C 4 )-alkyl group, a hydroxy-(C 2- C 3 )-alkyl group, a (C 1- C 4 )-alkoxy-(C 2- C 3 )-alkyl group, an amino-(C 2- C 3 )-alkyl group in which the amino group can also have one or two (C 1- C 4 )-alkyl radicals, or a 2,3-dihydroxypropyl group provided that not all substituents R 1 to R 6 are simultaneously hydrogen, and R 1 and R 2 and/or R 3 and R 4 and/or R 5 and R 6 along with the nitrogen atom to which they are attached are also an aziridine ring, an azetidine ring, a pyrrolidine ring, a piperidine ring, an azepane ring, an azocine ring or a morpholino group, thiomorpholino group or piperazino group which has another substituent R 7 on the nitrogen atom which is selected from hydrogen, a (C 1- C 4 )-alkyl group, a hydroxy-(C 2- C 3 )-alkyl group, a (C 1- C 4 )-alkoxy-(C 2- C 3 )-alkyl group, an amino-(C 2- C 3 )-alkyl group, or a 2,3-dihydroxypropyl group, and the three remaining hydrogen atoms on the benzol ring can also be replaced independently of each other by a halogen atom or a (C 1- C 4 )-alkyl group, or the physiologically tolerable salts thereof with inorganic and organic acids. Shades of color are obtained which have a high level of brilliancy and color fastness.

  该发明涉及氧化着色剂，特别适用于着色角蛋白纤维，并提供了一种着色这种纤维的方法。这些着色剂包含至少一种二氨基苯胺的初级氧化染料，其通式为（I），其中R1到R6独立地是氢，（C1-C4）烷基，羟基（C2-C3）烷基，（C1-C4）烷氧基（C2-C3）烷基，氨基（C2-C3）烷基，其中氨基团也可以有一个或两个（C1-C4）烷基基团，或2,3-二羟基丙基基团，前提是R1到R6的所有取代基不同时是氢，且R1和R2和/或R3和R4和/或R5和R6连同它们连接的氮原子也是氮杂环丙烷环，氮杂环丁烷环，吡咯烷环，哌啶环，氮杂庚烷环，氮杂环庚烷环或吗啉基，硫代吗啉基或哌嗪基，其在氮原子上还有另一个取代基R7，选自氢，（C1-C4）烷基，羟基（C2-C3）烷基，（C1-C4）烷氧基（C2-C3）烷基，氨基（C2-C3）烷基，或2,3-二羟基丙基基团，苯环上的其余三个氢原子也可以独立地被卤原子或（C1-C4）烷基取代，或其与无机和有机酸的生理耐受盐。获得的色彩具有高度的光泽度和色牢度。
• FÄRBEMITTEL
  申请人：Hans Schwarzkopf GmbH & Co. KG

  公开号：EP0910332A2

  公开（公告）日：1999-04-28
• OXIDATIONSFÄRBEMITTEL
  申请人：Hans Schwarzkopf GmbH & Co. KG

  公开号：EP0912160A2

  公开（公告）日：1999-05-06
• [DE] FÄRBEMITTEL<br/>[EN] DYES<br/>[FR] COLORANTS
  申请人：——

  公开号：WO1998001105A2

  公开（公告）日：1998-01-15

  [EN] Agents for dyeing keratinic fibres contain as direct-dyeing agent a 4-nitroaniline derivative of formula (I), or a physiologically tolerable salt thereof with an inorganic or organic acid. In formula (I), R1, R2, R3 and R4 represent independently of each other a hydrogen atom, an alkyl, hydroxyalkyl, alkoxyalkyl, carbamylalkyl, mesylaminoalkyl, acetylaminoalkyl, ureidoalkyl, carbalkoxyaminoalkyl, sulphalkyl, piperidinoalkyl, morpholinoalkyl or phenyl radical, which may be para-substituted by an amino group, these alkyl or alkoxy groups having 1 to 4 carbon atoms, provided that not all four substituents R1, R2, R3 and R4 simultaneously represent hydrogen. The groups -NR1-R2 and/or -NR3R4 may also represent an aziridine, azetidine, pyrrolidine, piperidine, azepan, azocin, morpholine, thiomorpholine or piperazine ring which may also bear at the nitrogen atom another substituent R8. R8 stands for a hydrogen atom, a (C1-C4)-alkyl, a hydroxy(C2-C3)-alkyl, a (C1-C4)-alkoxy-(C2-C3)-alkyl, an amino-(C2-C3)-alkyl or a 2,3-dihydroxypropyl group, and R5, R6 and R7 represent independently of each other a hydrogen atom, a halogen atom, a (C1-C4)-alkyl, a (C1-C4)-alkoxy radical, a carboxyalkyl, sulphalkyl or (C2-C4)-hydroxyalkyl radical. These compounds generate brilliant colours with high fastness. The number of tones may be further increased by adding other direct-dyeing agents or oxidation dye precursors.
  [FR] Les colorants décrits de fibres kératiniques contiennent, en tant qu'agent colorant montant directement sur la fibre, un dérivé de 4-nitroaniline qui répond à la formule (I) ou un sel physiologiquement admissible de ces composés avec un acide inorganique ou organique. Dans la formule (I), R1, R2, R3 et R4 représentent indépendamment les uns des autres un atome d'hydrogène, un radical alkyle, hydroxyalkyle, alcoxyalkyle, carbamylalkyle, mésylaminoalkyle, acétylaminoalkyle, uréidoalkyle, carbalcoxyaminoalkyle, sulfalkyle, pipéridinoalkyle, morpholinoalkyle ou phényle, le cas échéant para-substitué par un groupe amino, ces groupes alkyle ou alcoxy ayant 1 à 4 atomes de carbone, à condition que les quatre substituants R1, R2, R3 et R4 ne représentent pas tous en même temps hydrogène. Les groupes -NR1R2 et/ou -NR3R4 peuvent également désigner un cycle aziridine, azétidine, pyrrolidine, pipéridine, azépane, azocine, morpholine, thiomorpholine ou pipérazine, qui peut également porter sur l'atome d'azote un autre substituant R8, R8 désignant un atome d'hydrogène, un groupe alkyle (C1-C4), un groupe hydroxyalkyle (C2-C3), un groupe alcoxy-(C1-C4)-alkyle-(C2-C3), un groupe aminoalkyle (C2-C3) ou un groupe 2,3-dihydroxypropyle. Dans la formule R5, R6 et R7 désignent indépendamment les uns des autres un atome d'hydrogène, un atome d'halogène, un radical alkyle (C1-C4), un radical alcoxy (C1-C4), un radical carboxyalkyle, sulfo-alkyl ou hydroxyalkyle (C2-C4). Ces composés permettent d'obtenir des colorations brillantes très solides. Le nombre de nuances peut être encore accru par adjonction d'autres colorants montant directement sur la fibre ou d'autres précurseurs de colorants par oxydation.
  [DE] Mit Mitteln zum Färben von Keratinfasern, die als direktziehenden Farbstoff ein 4-Nitroanilin-Derivat der Formel (I), in der R1, R2, R3 und R4 unabhängig voneinander stehen für ein Wasserstoffatom, einen Alkyl-, Hydroxyalkyl-, Alkoxyalkyl-, Carbamylalkyl-, Mesylaminoalkyl-, Acetylaminoalkyl-, Ureidoalkyl-, Carbalkoxyaminoalkyl-, Sulfalkyl-, Piperidinoalkyl-, Morpholinoalkyl- oder einen Phenylrest, der gegebenenfalls in para-Position mit einer Aminogruppe substituiert ist, wobei diese Alkyl- oder Alkoxygruppen ein bis vier Kohlenstoffatome aufweisen, mit der Massgabe, dass nicht alle vier Substituenten R1, R2, R3 und R4 gleichzeitig für Wasserstoff stehen, und die Gruppen -NR1-R2 und/oder -NR3R4 auch stehen können für einen Aziridin-, Azetidin-, Pyrrolidin-, Piperidin-, Azepan-, Azocin-, Morpholin-, Thiomorpholin- oder einen Piperazin-Ring, der am Stickstoffatom auch einen weiteren Substituenten R8 tragen kann, wobei R8 ein Wasserstoffatom, ein (C1-C4)-Alkyl-, eine Hydroxy-(C2-C3)-alkyl-, eine (C1-C4)-Alkoxy-(C2-C3)-alkyl-, eine Amino-(C2-C3)-alkyl- oder eine 2,3-Dihydroxypropylgruppe ist, und R5, R6 und R7 unabhängig voneinander für ein Wasserstoffatom, ein Halogenatom, einen (C1-C4)-Alkyl-, einen (C1-C4)-Alkoxyrest, einen Carboxy-, Sulfo- oder einen (C2-C4)-Hydroxyalkylrest stehen, oder ein physiologisch verträgliches Salz dieser Verbindungen mit einer anorganischen oder organischen Säure enthalten, lassen sich brillante Färbungen mit hohen Echtheiten erzeugen. Die Zahl der Farbnuancen kann durch Zugabe weiterer Direktzieher oder Oxidationsfarbstoffvorprodukte weiter erhöht werden.