2-(4-nitrophenyl)benzo[b]thiophene | 54492-94-3

• 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: 2-(4-nitrophenyl)benzo[b]thiophene
• 英文别名: 2-(4-nitrophenyl)-1-benzothiophene
• CAS: 54492-94-3
• 化学式: C₁₄H₉NO₂S
• 分子量: 255.297
• InChiKey: VBWMAHYMJMKNKY-UHFFFAOYSA-N

物化性质

• 熔点：
  201-202 °C
• 沸点：
  442.0±20.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)benzo[b]thiophene 在 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 2-(4-aminophenyl)benzothiophene
  参考文献：
  名称：

  Discovery of novel N-(5-(tert-butyl)isoxazol-3-yl)-N′-phenylurea analogs as potent FLT3 inhibitors and evaluation of their activity against acute myeloid leukemia in vitro and in vivo

  摘要：

  FLT3 inhibitors have been explored as a viable therapy for acute myeloid leukemia (AML). However, the clinical outcomes of these FLT3 inhibitors were underwhelming except AC220. Therefore, the development of novel FLT3 inhibitors with high potency against both FLT3-WT and FLT3-ITD mutants are strongly demanded at the present time. In this study, we designed and synthesized a series of novel N-(5-(tert-butyl) isoxazol-3-yl)-N'-phenylurea derivatives as FLT3 inhibitors. SAR studies focused on the fused rings led to the discovery of a series of compounds with high potency against FLT3-ITD-bearing MV4-11 cells and significantly inhibitory activity toward FLT3. Among these compounds, N-(5-(tert-butyl) isoxazol-3-yl)-N'-(4-(7-methoxyimidazo[1,2-a]pyridin-2-yl)phenyl) urea (16i), displayed acceptable aqueous solubility, desirable pharmacokinetic profile and high cytotoxicity selectivity against MV4-11 cells. This compound can inhibit phosphorylation of FLT3 and induce apoptosis in a concentration-dependent manner. Further in vivo antitumor studies showed that 16i led to complete tumor regression in the MV4-11 xenograft model at a dose of 60 mg/kg/d while without observable body weight loss. This study had provided us a new chemotype of FLT3 inhibitors as novel therapic candidates for AML. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2015.06.033
• 作为产物：
  描述：

  2-氨基茴香硫醚 在 fluoroboric acid 、 溶剂红 43 、 sodium nitrite 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 14.67h， 生成 2-(4-nitrophenyl)benzo[b]thiophene
  参考文献：
  名称：

  Visible Light Photocatalytic Synthesis of Benzothiophenes

  摘要：

  The photocatalytic reaction of o-methylthio-arenediazonium salts with alkynes yields substituted benzothiophenes regioselectively through a radical annulation process. Green light irradiation of eosin Y initiates the photoredox catalysis. The scope of the reaction was investigated by using various substituted diazonium salts and different alkynes.

  DOI：

  10.1021/ol302517n

文献信息

• Ligand-free Pd/C-catalyzed Suzuki–Miyaura coupling reaction for the synthesis of heterobiaryl derivatives
  作者：Yoshiaki Kitamura、Satoko Sako、Takahiro Udzu、Azusa Tsutsui、Tomohiro Maegawa、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1039/b712207a

  日期：——

  We have developed a mild and efficient protocol for the ligand-free and heterogeneous Pd/C-catalyzed hetero Suzuki–Miyaura coupling reaction that allows for the synthesis of both heteroaryl–aryl and heteroaryl–heteroaryl derivatives in good to excellent yields.

  我们开发了一种温和高效的无配体和异质Pd/C催化的Suzuki–Miyaura耦合反应协议，可以在良好到优异的产率下合成异芳香族–芳香族和异芳香族–异芳香族衍生物。
• Microwave-assisted, ligand-free, direct C–H arylation of thiophenes in biomass-derived γ-valerolactone
  作者：Silvia Tabasso、Emanuela Calcio Gaudino、Laura Rinaldi、Audrey Ledoux、Paolo Larini、Giancarlo Cravotto

  DOI：10.1039/c7nj01540b

  日期：——

  Pd-catalyzed C–H arylation of heterocycles with aryl halides is a straightforward and more environmentally-friendly route to the synthesis of well-defined, pi-conjugated polymers for challenging applications in electronic devices. Although this type of transformation is more atom efficient than cross-couplings, it still poses environmental issues in the form of reaction media and the use of phosphine ligands

  Pd催化的杂环与芳基卤化物的C–H芳基化是合成明确定义的pi共轭聚合物的一种直接且对环境更友好的途径，可用于具有挑战性的电子设备中。尽管这种转化比交叉偶联在原子效率上更高，但它仍然以反应介质和膦配体的使用形式带来了环境问题。这项工作报道了噻吩的CH芳基化过程，对环境的影响大大改善，并且该方案有望用于合成规则的聚噻吩。γ-戊内酯（GVL）是一种无毒的生物质衍生溶剂，已用于该无膦微波辅助工艺中，并替代了常用的偶极非质子介质。活化的芳基溴化物以良好的收率得到芳基噻吩，而当存在吸电子基团时，使用碘化物并添加新戊酸。该反应还扩展到CH（杂）芳基化缩聚反应，使用低Pd负载量，以高收率和短反应时间获得了良好的区域规整性，从而获得了高分子量的聚（3-己基）噻吩。计算研究揭示了GVL在催化体系中作为配体的作用。
• <i>N</i>-Methylphthalimide-substituted benzimidazolium salts and PEPPSI Pd–NHC complexes: synthesis, characterization and catalytic activity in carbon–carbon bond-forming reactions
  作者：Senem Akkoç、Yetkin Gök、İlhan Özer İlhan、Veysel Kayser

  DOI：10.3762/bjoc.12.9

  日期：——

  novel benzimidazolium salts (1-4) and their pyridine enhanced precatalyst preparation stabilization and initiation (PEPPSI) themed palladium N-heterocyclic carbene complexes [PdCl2(NHC)(Py)] (5-8), where NHC = 1-(N-methylphthalimide)-3-alkylbenzimidazolin-2-ylidene and Py = 3-chloropyridine, were synthesized and characterized by means of (1)H and (13)C(1)H} NMR, UV-vis (for 5-8), ESI-FTICR-MS (for 2

  一系列新颖的苯并咪唑鎓盐（1-4）及其吡啶增强的以钯N-杂环卡宾络合物[PdCl2（NHC）（Py）]为主题的钯N-杂环卡宾络合物（5-8），其中NHC = 1- （N-甲基邻苯二甲酰亚胺）-3-烷基苯并咪唑啉-2-亚烷基和Py = 3-氯吡啶，并通过（1）H和（13）C （1）H} NMR，UV-vis（for 5 -8），ESI-FTICR-MS（适用于2、4、6-8）和FTIR光谱方法和元素分析。合成的化合物在Suzuki-Miyaura交叉偶联（对于1-8）和芳基化（对于5-8）反应中进行测试。作为催化剂，他们证明了形成不对称联芳基化合物的高效途径，即使它们以非常低的载量使用也是如此。例如，
• Infrared Irradiation‐Assisted Solvent‐Free Pd‐Catalyzed (Hetero)aryl‐aryl Coupling via C−H Bond Activation
  作者：Gianluigi Albano、Gianfranco Decandia、Maria Annunziata M. Capozzi、Nicola Zappimbulso、Angela Punzi、Gianluca M. Farinola

  DOI：10.1002/cssc.202101070

  日期：2021.8.23

  the development of green and sustainable methods for direct C−H bond arylation of (hetero)arenes. In this context, here the infrared (IR) irradiation-assisted solvent-free Pd-catalyzed direct C−H bond arylation of (hetero)arenes was achieved. Several heteroaryl-aryl coupling reactions were described, also involving heterocycles commonly used as building blocks for the synthesis of organic semiconductors

  对环境友好的合成方案的日益关注促进了针对（杂）芳烃直接 C−H 键芳基化的绿色和可持续方法的开发的研究。在此背景下，本文实现了红外（IR）辐射辅助的无溶剂 Pd 催化的（杂）芳烃的直接 C−H 键芳基化。描述了几种杂芳基-芳基偶联反应，还涉及通常用作有机半导体合成结构单元的杂环。该反应允许芳香核上的许多官能团。与热加热相比，红外辐射作为能源具有优势，并且与无溶剂条件相结合，为符合绿色化学原理的方案的开发做出了重要贡献。
• Palladacycles derived from arylphosphinamides for mild Suzuki–Miyaura cross-couplings
  作者：Guo-Jie Wu、Fu-She Han、Yu-Long Zhao

  DOI：10.1039/c5ra12742d

  日期：——

  of palladacycles, a wide variety of aryl bromides and boronic acids could be coupled very efficiently at ambient temperature and under air atmosphere without the need of external supporting ligands. Moreover, the mild conditions also allow for smooth coupling of electron-deficient, i.e., the less stable aryl triflates. In addition to the highly catalytic activity, the palladacyclic complexes can be

  我们介绍了一种衍生自芳基次膦酰胺的Palladacyclic配合物，可用作轻度的Suzuki-Miyaura交叉偶联的有效和通用的预催化剂。在存在1.0mol％的Palladacycles的情况下，可以在环境温度和空气气氛下非常有效地偶联各种各样的芳基溴化物和硼酸，而无需外部支持配体。此外，温和的条件还可以使电子不足的平滑耦合，即，不稳定的芳基三氟甲磺酸酯。除具有高催化活性外，还可以通过两步法很容易地从容易负担得起的二苯基次膦酰氯中制备四环化合物，并且对空气和湿气显示出极好的稳定性。由于这些突出的特性，新的palladacycles将在Suzuki-Miyaura联轴器中找到实际应用。