2,4,6-三硝基-N-(4-硝基苯基)苯胺 | 38417-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,4,6-三硝基-N-(4-硝基苯基)苯胺
• 英文名称: N-(p-nitrophenyl)picrylamine
• 英文别名: 2,4,6,4'-tetranitrodiphenylamine；2,4,4',6-tetranitrodiphenylamine；2,4,6-Trinitro-N-(4-nitrophenyl)aniline
• CAS: 38417-97-9
• 化学式: C₁₂H₇N₅O₈
• 分子量: 349.216
• InChiKey: XPASUWOQXAHESL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  195
• 氢给体数：
  1
• 氢受体数：
  9

安全信息

• 海关编码：
  2921420090

反应信息

• 作为反应物：
  描述：

  2,4,6-三硝基-N-(4-硝基苯基)苯胺 在 硝酸 、 溶剂黄146 作用下， 生成 N-(2,4-二硝基苯基)-2,4,6-三硝基苯胺
  参考文献：
  名称：

  Juillard, Bulletin de la Societe Chimique de France, 1905, vol. <3>33, p. 1173

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三硝基二苯基胺 在 硝酸 作用下， 生成 2,4,6-三硝基-N-(4-硝基苯基)苯胺
  参考文献：
  名称：

  van Duin; van Lennep, Recueil des Travaux Chimiques des Pays-Bas, 1919, vol. 38, p. 367

  摘要：

  DOI：

文献信息

• Aromatic nucleophilic substitution reactions of 1-dialkylamino-substituted activated benzenes with various amines in dimethyl sulfoxide
  作者：Shizen Sekiguchi、Hiromi Ishikura、Yukitoshi Hirosawa、Nobuyuki Ono

  DOI：10.1016/s0040-4020(01)87755-3

  日期：1990.1

  In the reactions of 1-d1a1kylamino-2,4,6-trinitro- and 1-dialkylam1no-2, 4-dinitrobenzenes with various amines in dimethyl sulfoxide, 1-dialkylamino group is easily replaced with primary n-alkylamines at room temperature, and in a low yield with pyrrolidine only among secondary amines.

  在二甲基亚砜中1-d1a1kylamino-2,4,6-三硝基和1-dialkam1no-2、4-二硝基苯与各种胺的反应中，1-二烷基氨基很容易在室温下被伯正烷基胺取代，并且仅仲胺中吡咯烷的收率低。
• Synthesis and biological evaluation of 2,4,6-trinitroaniline derivatives as potent antitumor agents
  作者：Nelin Hacıoğlu、Tuğba Güngör、Esra Tokay、Ferah Cömert Önder、Mehmet Ay、Feray Köçkar

  DOI：10.1007/s00706-020-02690-7

  日期：2020.10

  Abstract Nitro group-containing compounds are well known as effective anticancer drugs. The aim of the study is to synthesize a series of trinitroaniline derivatives to determine their potential antitumor activities on diverse cancer cell models, anti-apoptotic and anti-metastatic features on hepatoma cells. The anti-proliferative studies show that IC50 values of N-phenyl-2,4,6-trinitroaniline, N-(2

  摘要 含硝基基团的化合物是众所周知的有效抗癌药。该研究的目的是合成一系列三硝基苯胺衍生物，以确定其在多种癌细胞模型上的潜在抗肿瘤活性，在肝癌细胞上的抗凋亡和抗转移特性。抗增殖的研究表明，IC 50的值ñ -苯基-2,4,6- trinitroaniline，ñ - （2,4,6-三硝基苯基）萘-1-胺，ñ - （2,4,6-三硝基苯萘-2-胺，N-（3-硝基苯基）-2,4,6-三硝基苯胺与Hep3B细胞中顺铂的IC 50值相似。实际上，IC 50的N值-（3,5-二氟苯基）-2,4,6-三硝基苯胺比顺铂更好。此外，所有化合物均可降低细胞周期检查点蛋白cyclin D1的表达。为了研究化合物对细胞凋亡途径的影响，采用qRT-PCR和Western blot分析了Bcl-2和Bax的mRNA和蛋白表达。膜联蛋白V染色测定法，细胞凋亡的mRNA和蛋白质的分析表明，ñ -异丙基-2,4,6- trinitroaniline，ñ
• The activation of SNAr reactions by the superstrong electron-withdrawing substituent CF3S(O)=NSO2CF3
  作者：V.N. Boiko、N.V. Kirii、L.M. Yagupolskii

  DOI：10.1016/0022-1139(93)02959-i

  日期：1994.5

  4-trifluoromethylsulphonylderivative and picryl chloride in nucleophilic substitution. During interaction with hard nucleophilic agents, the effect of one superstrong substituent approximately corresponds to the influence of two nitro groups in positions 2 and 4. With soft reagents, picryl chloride is more active than the compound containing the CF3S(O)=NSO2CF3 group, polarizable only with difficulty.

  比较了在位置4包含超强吸电子取代基CF 3 S（O）= NSO 2 CF 3的2-硝基氯苯衍生物的氯稳定性与亲核取代中类似的4-三氟甲基磺酰基衍生物和苦瓜酰氯的比较。与硬亲核试剂相互作用期间，一个超强取代基的作用大约对应于位置2和4上两个硝基的影响。对于软试剂，氯化吡啶比含CF 3 S（O）= NSO的化合物更具活性。2 CF 3组，仅难极化。
• New Application of Crown Ether. V. The Effect of Crown Ethers on the Acid–Base Interaction between 2,4,4′,6-Tetranitrodiphenylamine and Primary Amines in Benzene
  作者：Fumio Wada、Yoshiko Wada、Kiyoshi Kikukawa、Tsutomu Matsuda

  DOI：10.1246/bcsj.54.458

  日期：1981.2

  The effect of crown ethers on the acid-base interaction of 2,4,4′,6-tetranitrodiphenylamine (HA, λmax 380 nm, pKa=8.88 in water) with primary amines (RNH2) in benzene was investigated spectrophotometrically. Crown ethers assisted strongly the formation of association complexes, R\overset+NH3·crown ether·A−, which existed as a single chemical species (λmax 478 nm) assignable to “crown ether-separated

  冠醚对苯中的 2,4,4',6-四硝基二苯胺 (HA, λmax 380 nm, pKa=8.88 in water) 与伯胺 (RNH2) 在苯中的酸碱相互作用的影响进行了分光光度法研究。冠醚强烈地协助形成缔合复合物，R\overset+NH3·冠醚·A-，其作为可归属于“冠醚分离的离子对”的单一化学物质（λmax 478 nm）存在。在18-crown-6和benzo-18-crown-6体系的平衡常数和热力学参数的基础上，讨论了各种伯胺的空间因子对平衡形成缔合配合物的影响。
• English rural societies and geographical marital endogamy, 1700–1837
  作者：K. D. M. Snell

  DOI：10.1111/1468-0289.00221

  日期：2002.5

  This article studies 69 rural parishes in eight English counties, examining changes in geographical marital endogamy. It discovers a consistent upward trend in the proportions of marriages that were parochially endogamous, coupled with a decline in so –called ‘foreign’ marriages following Hardwickes’s Act (1753), and a striking shift towards marriages taking place in the brides’ parishes. It explores regional variability in parochial endogamy and stresses the role of settlement sizes. The explanation for rising endogamy highlights factors such as population growth, rising poor relief expenditures, and attitudes resistant to ‘outsiders’ during a period of precarious subsistence and associated tensions.