4-硝基-4'-(乙酰氨基)联苯 | 28533-02-0

• 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: 4-硝基-4'-(乙酰氨基)联苯
• 中文别名: 甲基N-乙酰基-N-[(4-氨基苯基)磺酰]甘氨酸酸酯
• 英文名称: 4'-nitrobiphenyl-4-acetanilide
• 英文别名: 4-acetamido-4'-nitrobiphenyl；N-(4'-nitro-biphenyl-4-yl)-acetamide；N-(4'-Nitro-biphenyl-4-yl)-acetamid；4'-Nitro-4-acetamino-diphenyl；4'-Nitro-4-acetamido-biphenyl；4'-Nitro-4-biphenylacetanilid；4-Nitro-4'-(acetylamino)biphenyl；N-[4-(4-nitrophenyl)phenyl]acetamide
• CAS: 28533-02-0
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: BVLPGPPHLSHWBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  4-硝基-4'-(乙酰氨基)联苯 在 ammonium sulfide 作用下， 以 吡啶 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 N-acetoxy-N,N'-diacetylbenzidine
  参考文献：
  名称：

  乙酰化在犬肝和大鼠肝中联苯胺代谢和DNA加合物形成中的作用。

  摘要：

  为了确定联苯胺在狗（如大鼠）中是否被乙酰化，用狗和大鼠肝脏切片评估联苯胺的代谢。将切片与0.05 mM [3M]联苯胺孵育4小时。分析了培养基和细胞DNA的乙酰化联苯胺代谢产物和加合物。在大鼠中，联苯胺迅速转化为乙酰化代谢产物。在1小时时，联苯胺，N-乙酰联苯胺和N，N'-二乙酰联苯胺分别占培养基中总放射性的5％，23％和54％。在2小时内，放射性的75％为N，N'-二乙酰基联苯胺。在狗中，4h放射性比联苯胺极性更大的代谢物中存在45％的放射性。在犬肝切片培养基中未观察到N-乙酰化代谢产物。为了鉴定乙酰化联苯胺DNA加合物，N-（脱氧鸟苷-8-基）-N，N' 制备2-二乙酰联苯并通过FAB MS鉴定。该核苷加合物用于合成N-（脱氧鸟苷-8-基）-N-乙酰联苯胺和N'-（脱氧鸟苷-8-基）-N-乙酰联苯胺。通过HPLC分析来自与[3 H]联苯胺一起孵育的切片的核苷加合物。通过这种分析方法，3

  DOI：

  10.1021/tx00047a011
• 作为产物：
  描述：

  1-溴-4-硝基苯 、 4-乙酰基氨基苯硼酸频哪醇酯 在 palladium on activated charcoal sodium phosphate 作用下， 以 水 、 异丙醇 为溶剂， 反应 10.0h， 以91%的产率得到4-硝基-4'-(乙酰氨基)联苯
  参考文献：
  名称：

  Heterogeneous Pd/C-catalyzed ligand-free Suzuki–Miyaura coupling reaction using aryl boronic esters

  摘要：

  Heterogeneous Pd/C-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl boronic esters with aryl bromides was successfully carried out in aqueous media at room temperature without the use of a ligand such as phosphine derivatives. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.017

文献信息

• Dual gold photoredox C(sp²)–C(sp²) cross couplings – development and mechanistic studies
  作者：Vincent Gauchot、Ai-Lan Lee

  DOI：10.1039/c6cc05078f

  日期：——

  A dual visible light photoredox and gold-catalysed C(sp2)-C(sp2) cross coupling is described. The success of this mild, oxidant- and base-free cross coupling is highly dependent on the amount of water...

  描述了双重可见光光氧化还原和金催化的C（sp2）-C（sp2）交叉偶联。这种温和，无氧化剂和无碱的交叉偶联的成功高度依赖于水的量...
• Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides
  作者：Antonio Monge、Juan A. Palop、Adela Lopez de Cerain、Virginia Senador、Francisco J. Martinez、Yolanda Sainz、Susana Narro、Estrella Garcia、Carlos de Miguel

  DOI：10.1021/jm00010a023

  日期：1995.5

  Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy. Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy. The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells. Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and/or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells. Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced. Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxides have reduction potentials significantly more positive than Tirapazamine (E(pc)-0.90 V). The most potent cytotoxins to cells in culture were the 6,7,-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine. The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity. Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro. In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine. This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.
• 215. Some new di- and tri-nitro-p-terphenyls
  作者：G. W. Gray、D. Lewis

  DOI：10.1039/jr9610001069

  日期：——
• 17. Aspects of polyphenyl chemistry. Part II. Synthesis of sexiphenyls
  作者：J. A. Cade、A. Pilbeam

  DOI：10.1039/jr9640000114

  日期：——
• Willstaetter; Kalb, Chemische Berichte, 1906, vol. 39, p. 3478
  作者：Willstaetter、Kalb

  DOI：——

  日期：——