N-(4-iodophenyl)-2-nitroaniline | 104096-04-0

• 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: N-(4-iodophenyl)-2-nitroaniline
• CAS: 104096-04-0
• 化学式: C₁₂H₉IN₂O₂
• 分子量: 340.12
• InChiKey: WXQWIEACEMJRDB-UHFFFAOYSA-N

物化性质

• 熔点：
  171-172 °C
• 沸点：
  409.0±30.0 °C(Predicted)
• 密度：
  1.795±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 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：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-iodophenyl)-2-nitroaniline 在 ammonium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以43%的产率得到N-(4-碘苯基)1,2-二氨基苯
  参考文献：
  名称：

  Lactol PAF antagonists

  摘要：

  这项发明涵盖了一般式I的化合物：##STR1## 其中W代表一种咪唑并[4,5-c]吡啶基团，可选地取代为一个或多个从C.sub.1 -C.sub.6烷基，C.sub.1 -C.sub.6烷氧基，卤素，CF和CN中选择的取代基；而Z，R.sup.1，R.sup.2，R.sup.3，R.sup.4，R.sup.5，R.sup.6是变量。这些化合物可用作血小板活化因子的拮抗剂。

  公开号：

  US05428168A1
• 作为产物：
  描述：

  4-硝基碘苯 在 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， -50.0~110.0 ℃ 、2.0 MPa 条件下， 反应 2.0h， 生成 N-(4-iodophenyl)-2-nitroaniline
  参考文献：
  名称：

  Selective Hydrogenation of Halogenated Nitroaromatics to Haloanilines in Batch and Flow

  摘要：

  The selective hydrogenation of functionalized nitroaromatics poses a major challenge from both academic as well as industrial viewpoints. As part of the CHEM21 initiative (www.chem21.eu), we are interested in highly selective, catalytic hydrogenations of halogenated nitroaromatics. Initially, the catalytic reduction of 1-iodo-4-nitrobenzene to 4-iodoaniline served as a model system to investigate commercial heterogeneous catalysts. After determining optimal hydrogenation conditions and profiling performances of the best catalysts, hydrogenations were transferred from batch to continuous flow. Finally, the optimized flow conditions were applied to transformations which represent important steps in the syntheses of the active pharmaceutical ingredients clofazimine and vismodegib.

  DOI：

  10.1021/acs.oprd.5b00170

文献信息

• Platelet activating factor antagonists
  申请人：Pfizer Inc.

  公开号：US04935430A1

  公开（公告）日：1990-06-19

  Platelet activating factor antagonists of formula (I): ##STR1## wherein R is phenyl or phenyl substituted by one or more substituents selected from nitro, halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl (C.sub.1 -C.sub.4) alkoxy, fluoro (C.sub.1 -C.sub.4) alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulphonyl, hydroxy, trifluoromethyl and cyano, or is phenyl fused to a dioxole ring; R.sup.1 and R.sup.2 are each independently H or C.sub.1 -C.sub.6 alkyl, or R.sup.1 and R.sup.2 together complete a pyrrolidinyl, piperidino, morpholino, piperazinyl, N-(C.sub.1 -C.sub.4 alkyl) piperazinyl or N-(C.sub.2 -C.sub.4 alkanoyl)-piperazinyl group; or R.sup.2 is H or C.sub.1 -C.sub.4 alkyl and R.sup.1 is CN, C.sub.3 -C.sub.7 cycloalkyl, aryl, heteroaryl or a C.sub.1 -C.sub.4 alkyl group substituted by one or more substituents selected from C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.4 alkoxycarbonyl, aryl or heteroaryl; Z is selected from C.sub.1 -C.sub.6 alkoxy, aryl (C.sub.1 -C.sub.4) alkoxy, hydroxy, and --NR.sup.4 R.sup.5 wherein each of R.sup.4 and R.sup.5 is independently H or C.sub.1 -C.sub.6 alkyl, or R.sup.4 and R.sup.5 together complete a pyrrolidinyl, piperidino, morpholino, piperazinyl or N-(C.sub.1 -C.sub.4 alkyl) piperazinyl group; Y is 1,4 phenylene or pyridine-2,5-diyl, and X is a 5 or 6 membered aromatic heterocyclic group containing one or more nitrogen atoms in its ring; which ring may be fused to a benzene ring or to a further 5- or 6-membered aromatic heterocyclic ring containing one or more nitrogen atoms, at least one of said heterocyclic rings optionally also containing an oxygen or sulphur atom, and being optionally substituted with one or more substituents selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, CF.sub.3 and CN; and their pharmaceutically acceptable salts.

  公式（I）的血小板活化因子拮抗剂：其中R是苯基或苯基，其上取代基可从硝基，卤素，C.sub.1-C.sub.4烷基，C.sub.1-C.sub.4烷氧基，芳基（C.sub.1-C.sub.4）烷氧基，氟基（C.sub.1-C.sub.4）烷氧基，C.sub.1-C.sub.4烷基硫基，C.sub.1-C.sub.4烷基磺酰基，羟基，三氟甲基和氰基中选择一个或多个取代基；或者是与二噁唑环融合的苯基；R.sup.1和R.sup.2分别独立地为H或C.sub.1-C.sub.6烷基，或者R.sup.1和R.sup.2一起形成吡咯啉基，哌啶基，吗啉基，哌嗪基，N-(C.sub.1-C.sub.4烷基)哌嗪基或N-(C.sub.2-C.sub.4烷酰基)-哌嗪基；或者R.sup.2为H或C.sub.1-C.sub.4烷基，R.sup.1为CN，C.sub.3-C.sub.7环烷基，芳基，杂环芳基或一个C.sub.1-C.sub.4烷基，其上取代基可从C.sub.3-C.sub.7环烷基，C.sub.1-C.sub.4烷氧羰基，芳基或杂环芳基中选择一个或多个取代基；Z从C.sub.1-C.sub.6烷氧基，芳基（C.sub.1-C.sub.4）烷氧基，羟基和--NR.sup.4R.sup.5中选择，其中R.sup.4和R.sup.5中的每一个独立地为H或C.sub.1-C.sub.6烷基，或者R.sup.4和R.sup.5一起形成吡咯啉基，哌啶基，吗啉基，哌嗪基或N-(C.sub.1-C.sub.4烷基)哌嗪基；Y为1,4-苯基或吡啶-2,5-二基，X为含有一个或多个氮原子的5或6成员芳香杂环基团；该环可能与苯环融合，或与进一步含有一个或多个氮原子的5-或6成员芳香杂环环融合，至少其中一个杂环环可选地还含有一个氧原子或硫原子，并可选地取代一个或多个取代基，所述取代基可从C.sub.1-C.sub.4烷基，C.sub.1-C.sub.4烷氧基，卤素，CF.sub.3和CN中选择；以及其药学上可接受的盐。
• Lactol PAF antagonists
  申请人：British Biotech Pharmaceuticals Limited

  公开号：US05428168A1

  公开（公告）日：1995-06-27

  The invention encompasses compounds of general formula I: ##STR1## wherein W represents an imidazo[4,5-c]pyridyl group, optionally substituted with one or more substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo, CF, and CN; and Z, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 are variables. These compounds are useful as antagonists of platelet activating factor.

  这项发明涵盖了一般式I的化合物：##STR1## 其中W代表一种咪唑并[4,5-c]吡啶基团，可选地取代为一个或多个从C.sub.1 -C.sub.6烷基，C.sub.1 -C.sub.6烷氧基，卤素，CF和CN中选择的取代基；而Z，R.sup.1，R.sup.2，R.sup.3，R.sup.4，R.sup.5，R.sup.6是变量。这些化合物可用作血小板活化因子的拮抗剂。
• Selenium‐Catalyzed Carbonylative Synthesis of 2‐Benzimidazolones from 2‐Nitroanilines with TFBen as the CO Source
  作者：Xinxin Qi、Rong Zhou、Jin‐Bao Peng、Jun Ying、Xiao‐Feng Wu

  DOI：10.1002/ejoc.201801739

  日期：2019.9

  A selenium‐catalyzed carbonylative reaction for the synthesis of 2‐benzimidazolones from 2‐nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene‐1,3,5‐triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2‐benzimidazolones were produced in moderate to excellent yields.

  已开发了一种硒催化的羰基化反应，用于从2-硝基苯胺合成2-苯并咪唑酮。在此策略中，为避免使用有毒的CO气体，TFBen（苯-1,3,5-三甲酸酯三甲酸酯）被用作固体和稳定的CO前体，并且生产了各种所需的2-苯并咪唑酮，其中中等至极好。产量。
• Alkyl 2-benzylidene-4-(2-alkylimidazopyrid-1-yl) benzoylacetate esters
  申请人：Pfizer Inc

  公开号：US05149814A1

  公开（公告）日：1992-09-22

  Intermediates useful in the synthesis of dihydropyridine platelet activating factor antagonists of the formula ##STR1## where R is phenyl or substituted phenyl; R.sup.3 is lower alkyl; Y is 1,4-phenylene and X is 2-alkylimidazopyridyl.

  用于合成二氢吡啶血小板活化因子拮抗剂的中间体，其化学式为##STR1##其中R是苯或取代苯; R.sup.3是较低的烷基; Y是1,4-苯撑基，X是2-烷基咪唑吡啶基。
• 1,4-dihydro-2-(4-[benzimidazol-l-yl]phenyl)-pyridines as platelet
  申请人：Pfizer Inc.

  公开号：US05063237A1

  公开（公告）日：1991-11-05

  Platelet activating factor antagonists of formula (I): ##STR1## wherein R is phenyl or phenyl substituted by one or more substituents selected from nitro, halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl(C.sub.1 -C.sub.4)alkoxy, fluoro(C.sub.1 -C.sub.4)alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulphonyl, hydroxy, trifluoromethyl and cyano, or is phenyl fused to a dioxole ring; R.sup.1 and R.sup.2 are each independently H or C.sub.1 -C.sub.6 alkyl, or R.sup.1 and R.sup.2 together complete a pyrrolidinyl, piperidino, morpholino, piperazinyl, N-(C.sub.1 -C.sub.4 alkyl)piperazinyl or N-(C.sub.2 -C.sub.4 alkanoyl)-piperazinyl group; R.sup.2 is H or C.sub.1 -C.sub.4 alkyl and R.sup.1 is CN, C.sub.3 -C.sub.7 cycloalkyl, aryl, heteroaryl or a C.sub.1 -C.sub.4 alkyl group substituted by one or more substituents selected from C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.4 alkoxycarbonyl, aryl or heteroaryl; Z is selected from C.sub.1 -C.sub.6 alkoxy, aryl(C.sub.1 -C.sub.4)alkoxy, hydroxy, and --NR.sup.4 R.sup.5 wherein each of R.sup.4 and R.sup.5 is independently H or C.sub.1 -C.sub.6 alkyl, or R.sup.4 and R.sup.5 together complete a pyrrolidinyl, piperidino, morpholino, piperazinyl or N-(C.sub.1 -C.sub.4 alkyl)piperazinyl group; Y is 1,4 phenylene or pyridine-2,5-diyl, X is a 5 or 6 membered aromatic heterocyclic group containing one or more nitrogen atoms in its ring; which ring may be fused to a benzene ring or to a further 5- or 6-membered aromatic heterocyclic ring containing one or more nitrogen atoms, at least one of said heterocyclic rings optionally also containing an oxygen or sulphur atom, and being optionally substituted with one or more substituents selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, CF.sub.3 and CN; and their pharmaceutically acceptable salts.

  公式（I）的血小板活化因子拮抗剂：其中R为苯基或苯基取代物，所述取代物从硝基，卤素，C.sub.1-C.sub.4烷基，C.sub.1-C.sub.4烷氧基，芳基（C.sub.1-C.sub.4）烷氧基，氟代（C.sub.1-C.sub.4）烷氧基，C.sub.1-C.sub.4烷硫基，C.sub.1-C.sub.4烷基磺酰基，羟基，三氟甲基和氰基中选择一个或多个取代；或为融合到二噁英环上的苯基；R.sup.1和R.sup.2各自独立为H或C.sub.1-C.sub.6烷基，或R.sup.1和R.sup.2一起形成吡咯烷基，哌啶基，吗啉基，哌嗪基，N-（C.sub.1-C.sub.4烷基）哌嗪基或N-（C.sub.2-C.sub.4烷酰基）-哌嗪基；其中R.sup.2为H或C.sub.1-C.sub.4烷基，R.sup.1为CN，C.sub.3-C.sub.7环烷基，芳基，杂环芳基或取代一个或多个取代物的C.sub.1-C.sub.4烷基，所述取代物从C.sub.3-C.sub.7环烷基，C.sub.1-C.sub.4烷氧羰基，芳基或杂环芳基中选择一个或多个；Z从C.sub.1-C.sub.6烷氧基，芳基（C.sub.1-C.sub.4）烷氧基，羟基和--NR.sup.4R.sup.5中选择，其中R.sup.4和R.sup.5各自独立为H或C.sub.1-C.sub.6烷基，或R.sup.4和R.sup.5一起形成吡咯烷基，哌啶基，吗啉基，哌嗪基或N-（C.sub.1-C.sub.4烷基）哌嗪基；Y为1,4-苯基或吡啶-2,5-二基，X为含有一个或多个氮原子的5或6元芳香杂环基，其环可以与苯环或另一个含有一个或多个氮原子的5-或6元芳香杂环环融合，所述杂环环中至少有一个可以选择性地含有氧原子或硫原子，并且可以取代一个或多个取代物，所述取代物从C.sub.1-C.sub.4烷基，C.sub.1-C.sub.4烷氧基，卤素，CF.sub.3和CN中选择一个或多个；以及其医药上可接受的盐。