(3-甲氧基苯基)-(4-硝基苯基)甲酮 | 62507-47-5

• 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: (3-甲氧基苯基)-(4-硝基苯基)甲酮
• 英文名称: (3-methoxyphenyl)(4-nitrophenyl)methanone
• 英文别名: 3-methoxy-4'-nitrobenzophenone；(3-methoxyphenyl)-(4-nitrophenyl)methanone
• CAS: 62507-47-5
• 化学式: C₁₄H₁₁NO₄
• 分子量: 257.246
• InChiKey: LLBPXWMMNBOWBP-UHFFFAOYSA-N

物化性质

• 熔点：
  80.5-81.5 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• 沸点：
  438.2±30.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-甲氧基苯基)-(4-硝基苯基)甲酮 在 palladium on activated charcoal 氢气 作用下， 生成 (4-Amino-phenyl)-(3-methoxy-phenyl)-methanone
  参考文献：
  名称：

  4-Substituted anilides as selective melatonin MT 2 receptor agonists

  摘要：

  A series of 4-substituted anilides with human melatonergic affinity is reported. Butyramides 26, 39, 42, 52, 57, and 58 all demonstrated subnanomolar MT2 binding affinity and MT2 selectivity of at least 70-fold over the MT1 receptor. Compound 26 demonstrated full agonism at the MT2 receptor. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.030
• 作为产物：
  描述：

  3-甲氧基苯甲醛 在 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 反应 3.0h， 生成 (3-甲氧基苯基)-(4-硝基苯基)甲酮
  参考文献：
  名称：

  Glycosylated derivatives of benzophenone, benzhydrol and benzhydril as potential venous antithrombotic agents

  摘要：

  A series of glycosylated derivatives of benzophenone, benzhydrol, and benzhydril has been synthesized and evaluated for potential activity as venous antithrombotic agents. Studies on structure-activity relationships revealed that compounds having an electron-withdrawing group in the benzhydril or benzhydrol moiety, and specifically those having the beta-D-xylopyranosyl structure in the sugar moiety, were good antithrombotic agents in a rat model of venous thrombosis.

  DOI：

  10.1021/jm00059a015

文献信息

• Enantioselective Diarylcarbene Insertion into Si–H Bonds Induced by Electronic Properties of the Carbenes
  作者：Liang-Liang Yang、Declan Evans、Bin Xu、Wen-Tao Li、Mao-Lin Li、Shou-Fei Zhu、K. N. Houk、Qi-Lin Zhou

  DOI：10.1021/jacs.0c04725

  日期：2020.7.15

  enantioselection usually depends on differences in steric interactions between prochiral substrates and a chiral catalyst. We have discovered a carbene Si-H insertion in which the enantioselectivity depends primarily on the electronic characteristics of the carbene substrate, and the log(er) values are linearly related to Hammett parameters. A new class of chiral tetraphosphate dirhodium catalysts was developed

  催化对映选择通常取决于前手性底物和手性催化剂之间空间相互作用的差异。我们发现了一种卡宾 Si-H 插入，其中对映选择性主要取决于卡宾底物的电子特性，并且 log(er) 值与哈米特参数线性相关。开发了一类新的手性四磷酸二铑催化剂，该催化剂在二芳基卡宾插入硅烷的 Si-H 键方面表现出优异的活性和对映选择性。计算和机械研究表明卡宾的两个芳基之间的电子差异如何导致非对映过渡态能量的差异。该研究为利用基材的电子特性进行不对称催化提供了一种新策略。
• Total Synthesis of Termicalcicolanone A via Organocatalysis and Regioselective Claisen Rearrangement
  作者：Saki Ito、Taiki Kitamura、Sundaram Arulmozhiraja、Kei Manabe、Hiroaki Tokiwa、Yumiko Suzuki

  DOI：10.1021/acs.orglett.9b00731

  日期：2019.4.19

  A total synthesis of an anticancer xanthone natural product termicalcicolanone A utilizing multiple nucleophilic aromatic substitutions and pericyclic reactions has been developed. The pyrano[3,2-b]xanthen-6-one scaffold was constructed via NHC-catalyzed aroylation to produce the benzophenone intermediate, Claisen cyclization to form the pyran ring, and intramolecular 1,4-addition to construct the

  已经开发了利用多个亲核性芳族取代和周环反应的抗癌黄酮天然产物termicalcicolanone A的全合成。吡喃并[3,2 - b ]黄嘌呤-6-骨架是通过NHC催化的芳基化反应生成的二苯甲酮中间体，经克莱森环化形成吡喃环，并通过分子内的1,4-加成反应构建an吨酮骨架。通过区域选择性克莱森重排在合成的最后阶段引入异戊二烯基。合成已通过19个步骤完成。
• Aerobic oxidative acylation of nitroarenes with arylacetic esters under mild conditions: facile access to diarylketones
  作者：Jiang-Sheng Li、Qian Yang、Fan Yang、Guo-Qin Chen、Zhi-Wei Li、Yin-Jie Kuang、Wei-Jing Zhang、Peng-Mian Huang

  DOI：10.1039/c7ob02865b

  日期：——

  A facile and regioselective base-mediated aerobic oxidative acylation of nitroarenes to access diarylketones under mild conditions has been developed. It features the use of bench-stable and readily available arylacetates as acyl surrogates, and the absence of transition-metals and synthetic oxidants. This protocol involves a cascade CDC/oxidative decarboxylation process.

  已经开发了在温和条件下容易和区域选择性的碱介导的硝基芳烃的好氧氧化酰化，以得到二芳基酮。它具有使用稳定的，易于获得的芳基乙酸酯作为酰基替代物的特点，并且不存在过渡金属和合成氧化剂。该方案涉及级联的CDC /氧化脱羧过程。
• In Situ Generation of Palladium Nanoparticles: Ligand-Free Palladium Catalyzed Pivalic Acid Assisted Carbonylative Suzuki Reactions at Ambient Conditions
  作者：Qing Zhou、Shaohua Wei、Wei Han

  DOI：10.1021/jo402366p

  日期：2014.2.7

  selective carbonylative Suzuki reactions of aryl iodides with arylboronic acids using an in situ generated nanopalladium system furnished products in high yields. The reactions were performed under ambient conditions and in the absence of an added ligand. The key to success is the addition of pivalic acid, which can effectively suppress undesired Suzuki coupling. The synthesis can be easily scaled up, and

  使用原位生成的纳米钯系统，芳基碘化物与芳基硼酸的高度选择性羰基化Suzuki反应可提供高收率的产品。反应在环境条件下和不存在添加的配体的情况下进行。成功的关键是添加新戊酸，它可以有效抑制不希望的Suzuki偶联。合成很容易扩大规模，催化体系最多可重复使用9次。讨论了活性催化物质的性质。
• Palladium-catalyzed cross-coupling of aroyl chlorides with aryl stannanes in the presence of triethylsilane: Efficient access to aromatic ketones
  作者：Shoko Higashi、Sota Uno、Yui Ohsuga、Maiko Noumi、Ryota Saito

  DOI：10.1016/j.tetlet.2020.152466

  日期：2020.11

  Herein, we report the development of a palladium-catalyzed cross-coupling reaction that focuses on the preparation of aromatic ketones. Aroyl chlorides react quickly at 120 °C with aryl stannanes in the presence of Pd(PPh3)4 and Et3SiH to efficiently give the corresponding ketones without the formation of significant decarbonylated byproducts. In other words, the decarbonylative side reaction is practically

  在本文中，我们报告了钯催化交叉偶联反应的发展，该反应侧重于芳族酮的制备。芳酰氯在Pd（PPh 3）4和Et 3 SiH的存在下在120°C下与芳基锡烷快速反应，以有效地提供相应的酮，而不会形成明显的脱羰副产物。换句话说，通过简单地将Et 3 SiH添加到反应混合物中实际上抑制了脱羰基副反应，这减少了产物中联芳基杂质的量。