1-(2-(2-硝基苯基)乙炔基)苯 | 35010-17-4

• 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: 1-(2-(2-硝基苯基)乙炔基)苯
• 英文名称: 1-nitro-2-phenylethynyl-benzene
• 英文别名: 1-nitro-2-(2-phenylethynyl)benzene；2-nitrodiphenylacetylene；1-(2-(2-nitrophenyl)ethynyl)benzene；2-(phenylethynyl)nitrobenzene；(2-nitrophenyl)phenylacetylene；Benzene, 1-nitro-2-(phenylethynyl)-
• CAS: 35010-17-4
• 化学式: C₁₄H₉NO₂
• 分子量: 223.231
• InChiKey: OXTHQALUIYPPEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-(2-硝基苯基)乙炔基)苯 在 indium(III) chloride 、 双(乙腈)氯化钯(II) 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 2-苯基吲哚-3-酮
  参考文献：
  名称：

  2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behaviour and antiplasmodial activities

  摘要：

  The synthesis of indolone derivatives and their antiplasmodial activity in vitro against Plasmodium falciparum at the blood stage are described. The 2-aryl-3H-indol-3-ones were synthesized via deoxygenation of indolone-N-oxides. Electrochemical behaviour, antiplasmodial activity and cytotoxicity on human tumor cell lines were compared to those of indolone-N-oxides. The antiplasmodial IC50 (concentrations at 50% inhibition) of these compounds ranged between 49 and 1327 nM. Among them, the 2(4-dimethylaminophenyl)-5-methoxy-indol-3-one, 7, had the best antiplasmodial activity in vitro (IC50 = 49 nM; FcB1 strain) and selectivity index (SI (CC50 MCF7/IC50 FcB1) = 423.4). Thus, the hits identified in this deoxygenated series correspond to their structural homologs in the N-oxide series with comparable electrochemical behaviour at the nitrogen-carbon double bond. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.059
• 作为产物：
  描述：

  (Z)-2-nitrostilbene 在 二硫化碳 、 sodium hydroxide 、 氯 作用下， 生成 1-(2-(2-硝基苯基)乙炔基)苯
  参考文献：
  名称：

  Zur Darstellung von 2-Phenyl-isatogen和2-Phenyl-6-carbäthoxy-isatogen

  摘要：

  DOI：

  10.1002/hlca.19370200136

文献信息

• Copper(<scp>i</scp>) catalyzed Sonogashira reactions promoted by monobenzyl nicotinium chloride, a N-donor quaternary ammonium salt
  作者：Abdol Reza Hajipour、Elaheh Boostani、Fatemeh Mohammadsaleh

  DOI：10.1039/c5ra19028b

  日期：——

  with copper(I) chloride was employed for the first time in Sonogashira cross-coupling reactions of phenylacetylene with various aryl halides. The goal was to use an efficient green media by using copper instead of palladium in metal-catalyzed coupling reactions. Monobenzyl nicotinium chloride, a quaternary ammonium salt containing a coordinating centre, plays an important role in this catalytic system

  在苯基乙炔与各种芳基卤化物的Sonogashira交叉偶联反应中，首次采用了一种新颖有效的催化体系，该体系采用氯化单苄基烟碱与氯化铜（I）结合。目标是通过在金属催化的偶联反应中使用铜代替钯来使用高效的绿色介质。单苄基氯化烟碱，一种含配位中心的季铵盐，在该催化体系中起重要作用，并提高了Cu（I）反应过程中的种类。在135–140°C下，短时间内在DMF中以中等至极好的收率生产了许多内部炔烃。将该催化体系的效率与由没有N-给体活性位点的二苄基氯化铵制得的铜基催化剂进行了比较，其中由于缺乏配位位点而观察到了较低的活性。
• Copper(0)/PPh₃-Mediated Bisheteroannulations of <i>o</i>-Nitroalkynes with Methylketoximes Accessing Pyrazo-Fused Pseudoindoxyls
  作者：Huanxin Meng、Zhenhua Xu、Zhonghua Qu、Huawen Huang、Guo-Jun Deng

  DOI：10.1021/acs.orglett.0c02180

  日期：2020.8.7

  A copper(0)/PPh3-mediated cascade bisheteroannulation reaction of o-nitroalkynes with methylketoximes has been developed that provides viable access to a diverse range of pyrazo-fused pseudoindoxyl compounds. Synthetically useful functional groups including sensitive C–I bonds are compatible with this system. Mechanistic studies suggest a reaction cascade involving sequential PPh3-mediated deoxygenative

  已开发出铜 (0)/PPh 3介导的邻硝基炔烃与甲基酮肟的级联双杂环化反应，该反应为获得各种吡唑稠合假吲哚化合物提供了可行的途径。合成有用的官能团包括敏感的 C-I 键与该系统兼容。机理研究表明，反应级联涉及连续 PPh 3介导的脱氧环异构化和铜催化的 [3 + 2] 吡唑环化。
• Palladium-catalyzed cross-coupling reaction of ethynylstibanes with organic halides
  作者：Naoki Kakusawa、Kouichiro Yamaguchi、Jyoji Kurita

  DOI：10.1016/j.jorganchem.2005.03.021

  日期：2005.6

  The reaction of ethynylstibanes (1a–g) with vinyl halides or triflate in the presence of a palladium catalyst led to the formation of cross-coupling products (5a–g, 10–12) in good to moderate yield, along with homo-coupling products (6a–g). A similar reaction of ethynyldiphenylstibane (1a) with aryl iodides (13a–i) also gave cross-coupling products (14a–i), although the yields were relatively low.

  在钯催化剂的存在下，乙炔基苯乙烯（1a – g）与卤化乙烯或三氟甲磺酸酯的反应导致形成交联产物（5a – g，10 – 12），具有良好至中等的收率以及均相偶联产品（6a–g）。乙炔基二苯基乙b （1a）与芳基碘化物（13a – i）的类似反应也产生交叉偶联产物（14a – i），尽管产量相对较低。交叉偶联产物的产率高度依赖于所用溶剂的性质，当反应在HMPA或胺（如二乙胺和吗啉）中进行时，可获得良好的结果。结果表明，HMPA和用作溶剂的胺可通过锑和氧（对于HMPA）或氮（对于胺）之间的分子间配位作用，促进1上的乙炔基向钯的金属转移。
• Pd/Cu-free Heck and Sonogashira cross-coupling reaction by Co nanoparticles immobilized on magnetic chitosan as reusable catalyst
  作者：Abdol R. Hajipour、Fatemeh Rezaei、Zahra Khorsandi

  DOI：10.1039/c6gc03377f

  日期：——

  The chitosan (CS) is a porous self-standing nanofibrillar microspheres which can be used as a metal carrier. Amino-groups on CS enable to modulation of cobalt coordination using safe organic ligand...

  壳聚糖（CS）是一种多孔的自立纳米原纤维微球，可以用作金属载体。CS上的氨基可以使用安全的有机配体来调节钴的配位...
• Phosphane-Free Copper-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Aryl Halides under Aerobic Conditions
  作者：Delin Pan、Chun Zhang、Shengtao Ding、Ning Jiao

  DOI：10.1002/ejoc.201100659

  日期：2011.7.18

  A phosphane-free copper-catalyzed decarboxylative cross-coupling reaction of alkynyl carboxylic acids with aryl halides was developed. CuBr (1–5 mol-%) was used as a catalyst in the presence of a β-diketone ligand in air. The reactions of aryl iodides were conducted in the absence of a Pd catalyst. The ligand plays a key role in this kind of copper catalysis. NaNO2 was disclosed to efficiently improve

  开发了一种无磷烷铜催化的炔基羧酸与芳基卤化物的脱羧交叉偶联反应。CuBr (1–5 mol-%) 在空气中存在 β-二酮配体的情况下用作催化剂。芳基碘化物的反应在不存在 Pd 催化剂的情况下进行。配体在这种铜催化中起着关键作用。当底物中不存在硝基时，NaNO 2 被公开以有效地改善这种脱羧交叉偶联。