4-碘-2-甲基-6-硝基苯胺 | 532934-93-3

• 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-碘-2-甲基-6-硝基苯胺
• 英文名称: 4-iodo-2-methyl-6-nitroaniline
• 英文别名: 4-iodo-6-methyl-2-nitroaniline；4-iodo-2-methyl-6-nitro-aniline；4-Jod-2-methyl-6-nitro-anilin；5-Jod-3-nitro-2-amino-toluol；4-iodo-2-methyl-6-nitrobenzenamine
• CAS: 532934-93-3
• 化学式: C₇H₇IN₂O₂
• mdl: MFCD09033134
• 分子量: 278.049
• InChiKey: QDOSZZJIJPEKSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2921430090

反应信息

• 作为反应物：
  描述：

  4-碘-2-甲基-6-硝基苯胺 在 potassium phosphate 、 palladium 10% on activated carbon 、 四丁基溴化铵 、 sodium acetate 、 palladium diacetate 、 三(邻甲基苯基)磷 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 N,N-二甲基乙酰胺 、 正丁醇 为溶剂， 反应 24.0h， 生成 trans-4-((7-chloro-4-((4-(2-cyanovinyl)-2-methyl-6-nitrophenyl)amino)quinazoline-2-yl)amino)benzonitrile
  参考文献：
  名称：

  Molecular Hybridization-Inspired Optimization of Diarylbenzopyrimidines as HIV-1 Nonnucleoside Reverse Transcriptase Inhibitors with Improved Activity against K103N and E138K Mutants and Pharmacokinetic Profiles

  摘要：

  Molecular hybridization is a powerful strategy in drug discovery. A series of novel diarylbenzopyrimidine (DABP) analogues were developed by the hybridization of FDA-approved drugs etravirine (ETR) and efavirenz (EFV) as potential HIV-1 nonnudeoside reverse transcriptase inhibitors (NNRTIs). Substituent modifications resulted in the identification of new DABPs with the combination of the strengths of the two drugs, especially compound lid, which showed promising activity toward the EFV-resistant K103N mutant. 12d also had a favorable pharmacokinetic (PK) profile with liver microsome clearances of 14.4 mu L/min/mg (human) and 33.2 mu L/min/mg (rat) and an oral bioavailability of 15.5% in rat. However, its activity against the E138K mutant was still unsatisfactory; E138K is the most prevalent NNRTI resistance-associated mutant in ETR treatment Further optimizations resulted in a highly potent compound (12z) with no substituents on the phenyl ring and a 2-methyl-6-nitro substitution pattern on the 4-cyanovinyl-2,6-disubstitued phenyl motif. The antiviral activity of this compound was much higher than those of ETR and EFV against the WT, E138K, and K103N variants (EC50 = 3.4, 4.3, and 3.6 nM, respectively), and the cytotoxicity was decreased while the selectivity index (SI) was increased. In particular, this compound exhibited acceptable intrinsic liver microsome stability (human, 34.5 mu L/min/mg; rat, 33.2 mu L/min/mg) and maintained the good PK profile of its parent compound EFV and showed an oral bioavailability of 16.5% in rat. Molecular docking and structure-activity relationship (SAR) analysis provided further insights into the binding of the DABPs with HIV-1 reverse transcriptase and provided a deeper understanding of the key structural features responsible for their interactions.

  DOI：

  10.1021/acsinfecdis.9b00229
• 作为产物：
  描述：

  AR-甲基-AR-硝基苯胺 在 N-碘代丁二酰亚胺 、 溶剂黄146 作用下， 反应 6.0h， 以97%的产率得到4-碘-2-甲基-6-硝基苯胺
  参考文献：
  名称：

  8-甲基喹喔啉在混合酸中的硝化

  摘要：

  8-甲基喹喔啉在 40-50 °C 下通过简单的混合酸硝化方案在 C-5 处被有效地硝化。讨论了 C-6 卤素官能化和混合酸条件的修改对相对转化率和工艺安全性的影响。6-卤代-8-甲基喹喔啉的竞争副反应包括在 C-6 的水解和在 C-7 或 C-5 的卤化。

  DOI：

  10.1021/op0340255

文献信息

• [EN] POLYHALOGENATED PROPENE BENZOQUINONE DIOXIME DERIVATIVES AND ITS USE AS PESTICIDES<br/>[FR] DERIVES DE PROPENE-BENZOQUINONE-DIOXIME POLYHALOGENES ET LEUR UTILISATION EN TANT QUE PESTICIDES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2006037496A1

  公开（公告）日：2006-04-13

  Novel dihalogenopropene derivatives of the formula (I) and of the formula (Ia), wherein A, A1, A2, G, Q, R1, R2, R3, R4, and X have the meaning provided in the description, Methods and intermediates for their production as well as their use for combattiing pests.

  具有以下公式(I)和公式(Ia)的新型二卤代丙烯衍生物，其中A、A1、A2、G、Q、R1、R2、R3、R4和X的含义如描述中所提供的含义，以及它们的生产方法和中间体，以及它们用于对抗害虫的用途。
• Chiral derivatives of 1,2-benzenedisulfonimide as efficient Brønsted acid catalysts in the Strecker reaction
  作者：Margherita Barbero、Silvano Cadamuro、Stefano Dughera、Roberta Torregrossa

  DOI：10.1039/c4ob00552j

  日期：——

  Two chiral derivatives of 1,2-benzenedisulfonimide were synthesized. (−)Atropisomers have been demonstrated to be efficient chiral catalysts in the Strecker reaction.

  通过合成了1,2-苯二磺酰亚胺的两种手性衍生物。已证明(−)异构体在Strecker反应中是高效的手性催化剂。
• Tetrabutylammonium Pyridin-2-olate: A New Reagent for the Efficient Synthesis of <i>N</i>-Aryl Pyridin-2-ones
  作者：Huiping Zhang、Bang-Chi Chen、Bei Wang、Sam Chao、Rulin Zhao、Ngiapkie Lim、Balu Balasubramanian

  DOI：10.1055/s-2008-1072569

  日期：2008.5

  A new reagent, tetrabutylammonium pyridin-2-olate, was prepared and its application to the efficient synthesis of N-aryl pyridine-2-ones was demonstrated using CuI-catalyzed coupling reactions with aryl iodides. This coupling reaction is mild, high-yielding, and remarkably chemoselective (N- vs. O-arylation). It is also compatible with substrates containing labile functional groups.

  制备了一种新试剂 吡啶-2-醇四丁基铵，并通过 CuI 催化与芳基碘化物的偶联反应证明了其在高效合成 N-芳基吡啶-2-酮中的应用。这种偶联反应温和、高产且具有显着的化学选择性（N- 与 O-芳基化）。它还与含有不稳定官能团的底物相容。
• Preparation of N-aryl pyridones
  申请人：Zhang Huiping

  公开号：US20060069260A1

  公开（公告）日：2006-03-30

  A novel process and intermediates thereof for making N-aryl pyridones of the type shown below from appropriate pyridinolates is described. These compounds are useful as intermediates for the synthesis of clinical candidates.

  本文介绍了一种从适当的吡啶醇盐制备下列类型的N-芳基吡啶酮的新工艺和中间体。这些化合物可用作合成临床候选药物的中间体。
• Heterocyclic compounds useful in the treatment of neoplastic diseases, inflammatory disorders and immunomodulatory disorders
  申请人：Anikin Alexey Vyacheslavovich

  公开号：US20080207635A1

  公开（公告）日：2008-08-28

  The present invention provides compounds capable of modulating tyrosine kinases, compositions comprising the compounds and methods of their use.

  本发明提供了能够调节酪氨酸激酶的化合物，包括这些化合物的组合物和使用它们的方法。