N-(4-碘苯基)1,2-二氨基苯 | 122957-29-3

• 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: N-(4-碘苯基)1,2-二氨基苯
• 英文名称: N-(4-iodophenyl)benzene-1,2-diamine
• 英文别名: N-(4-iodophenyl)1,2-diaminobenzene；N-(4-iodophenyl)-2-aminoaniline；2-N-(4-iodophenyl)benzene-1,2-diamine
• CAS: 122957-29-3
• 化学式: C₁₂H₁₁IN₂
• 分子量: 310.137
• InChiKey: HIADXXVQRNYRGG-UHFFFAOYSA-N

物化性质

• 沸点：
  389.7±27.0 °C(Predicted)
• 密度：
  1.724±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 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：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-碘苯基)1,2-二氨基苯 、 乙基乙酰亚胺盐酸盐 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(4-iodophenyl)-2-methylbenzimidazole
  参考文献：
  名称：

  Platelet activating factor antagonists

  摘要：

  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。

  公开号：

  US04935430A1
• 作为产物：
  描述：

  4-硝基碘苯 在 对甲苯甲醚 、 二乙二醇二丁醚 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， -50.0~100.0 ℃ 、8.5 MPa 条件下， 反应 6.0h， 生成 N-(4-碘苯基)1,2-二氨基苯
  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

• 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。
• 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。
• Alkyl 2-benzylidene-4-(benzimidazol-1-yl) benzoylacetate esters as
  申请人：Pfizer Inc.

  公开号：US05070205A1

  公开（公告）日：1991-12-03

  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 a benzimidazol-1-yl.

  在合成二氢吡啶血小板活化因子拮抗剂的中间体中有用的化合物的化学式如下：##STR1## 其中R为苯基或取代苯基；R.sup.3为低碳基；Y为1,4-苯基；X为苯并咪唑-1-基。
• Benzimidazole compounds, their preparation and use
  申请人：NEUROSEARCH A/S

  公开号：EP0604353A1

  公开（公告）日：1994-06-29

  The present invention discloses compounds of the formula or a pharmaceutically-acceptable addition salt thereof wherein R' and R'' independently of each other are hydrogen or alkyl, or R' and R'' together form a 3 to 6 membered alkylene chain; one of R¹ and R² is aryl which may be substituted one or more times with halogen, CF₃, CN, OH, alkyl, cycloalkylalkyl, alkenyl, alkynyl, alkoxy, amino, nitro, sulphamoyl, tetrazolyl, CO₂H, CO₂-alkyl and the other of R¹ and R² is hydrogen, halogen, alkoxy, amino or alkyl; and R⁴, R⁵, R⁶ and R⁷ independently of each other are hydrogen, halogen, amino, nitro, CN, OH, CF₃, alkyl or alkoxy; and n is 0 or 1; provided that neither of R¹ and R² is phenyl or substituted phenyl when n is 0. The compounds are useful as pharmaceuticals, for example, in the treatment of ischemia, anoxia, migraine and psychosis.

  本发明公开了如下式的化合物 或其药学上可接受的加成盐 其中 R'和 R''各自独立地为氢或烷基，或 R'和 R''共同形成 3 至 6 个成员的亚烷基链； R¹ 和 R² 中的一个为芳基，可被卤素、CF₃、CN、OH、烷基、环烷基、烯基、炔基、烷氧基、氨基、硝基、氨基磺酰基、四唑基、CO₂H、CO₂-烷基取代一次或多次，R¹ 和 R² 中的另一个为氢、卤素、烷氧基、氨基或烷基；以及 R⁴、R⁵、R⁶ 和 R⁷ 相互独立地为氢、卤素、氨基、硝基、CN、OH、CF₃、烷基或烷氧基；且 n 为 0 或 1；但当 n 为 0 时，R¹ 和 R² 均不是苯基或取代苯基。 这些化合物可用作药物，例如用于治疗缺血、缺氧、偏头痛和精神病。