(2-氯苯基)(4-硝基苯基)甲酮 | 77778-73-5

• 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: (2-氯苯基)(4-硝基苯基)甲酮
• 英文名称: (2-chlorophenyl)(4-nitrophenyl)methanone
• 英文别名: 2-chloro-3'-nitrobenzophenone；2-chloro-4'-nitro-benzophenone；(2-Chlor-phenyl)-(4-nitro-phenyl)-keton；2-Chlor-4'-nitro-benzophenon；2-Chlor-4'-nitrobenzophenon；2-Chloro-4'-nitrobenzophenone；(2-chlorophenyl)-(4-nitrophenyl)methanone
• CAS: 77778-73-5
• 化学式: C₁₃H₈ClNO₃
• 分子量: 261.664
• InChiKey: HQHOYTXNCOKBNE-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  423.3±25.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  (2-氯苯基)(4-硝基苯基)甲酮 、 phenylmagnesium bromide 生成 (2-chloro-4-nitrophenyl)diphenylcarbinol
  参考文献：
  名称：

  Triaryl methane derivatives as antiproliferative agents

  摘要：

  Clotrimazole (CLT) 1, a synthetic anti-fungal imidazole derivative, inhibits tumor cell proliferation and angiogenesis. In the current study, flow cytometric analysis demonstrated that the decrease in tumor cell growth by CLT I was associated with inhibition of cell cycle progression at the G(1)-S phase transition, resulting in GO-G, arrest. A series of CLT I analogues has been generated in order to develop CLT I derivatives that are devoid of the imidazole moiety which is responsible for the hepatoxicity associated with CLT I while retaining CLT I efficacy. The majority of these analogues demonstrate in vitro antiproliferative activity ranging from submicromotar to micromolar concentrations. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.004
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 (2-氯苯基)(4-硝基苯基)甲酮
  参考文献：
  名称：

  Montagne, Chemische Berichte, 1916, vol. 49, p. 2274

  摘要：

  DOI：

文献信息

• Psychotropic derivatives of 5-phenyl-7-chloro-1,3-dihydro-1,4-benzodiazepin-2-one and contribution to the synthesis of its 5-(2-chlorophenyl) analogue
  作者：Zdeněk Vejdělek、Miroslav Rajšner、Antonín Dlabač、Miroslav Ryska、Jiří Holubek、Emil Svátek、Miroslav Protiva

  DOI：10.1135/cccc19803593

  日期：——

  Alkylation of 7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one (I) with 2,5-dimethoxyphenacyl bromide and 3-(4-phenylpiperazino)propyl chloride afforded the N-substituted derivatives of nordazepam III and IV; compound IV revealed properties of a potential hypnotic agent. Reaction of 4-chloronitrobenzene with (2-chlorophenyl)acetonitrile in methanolic solutions of alkali hydroxides gave mixtures from which the following compounds were isolated: 5-chloro-3-(2-chlorophenyl)-2,1-benzisoxazole (VII), the O-methyloxime X, 5-chloro-2,3-bis(2-chlorophenyl)indole (XI), 2-chloro-4'-nitrobenzophenone (XVII) and 2-chloro-9-cyanoacridine N-oxide (XX). A similar reaction of 4-chloronitrobenzene with (2-fluorophenyl)acetonitrile gave compound XX as the main product; in smaller amounts 4-nitroanisole, 2-fluoro-4'-nitrobenzophenone (XVIII) and 2-chloroacridine-9-carbonitrile (XXIV) were obtained. Compound VII was reduced to the aminobenzophenone derivative V which was transformed via the phthalimidoacetyl derivative VI to the chlorodemethyldiazepam II.

  将7-氯-5-苯基-1,3-二氢-1,4-苯二氮杂环己-2-酮（I）与2,5-二甲氧基苯乙酰溴和3-(4-苯基哌嗪基)丙基氯烷基化，得到了诺多西泮（III）和（IV）的N-取代衍生物；化合物（IV）表现出潜在催眠药物的特性。4-氯硝基苯与(2-氯苯基)乙腈在碱性氢氧化物甲醇溶液中反应，得到混合物，从中分离出以下化合物：5-氯-3-(2-氯苯基)-2,1-苯并异噁唑（VII）、O-甲氧基肟（X）、5-氯-2,3-双(2-氯苯基)吲哚（XI）、2-氯-4'-硝基苯基酮（XVII）和2-氯-9-氰基喹啉-N-氧化物（XX）。4-氯硝基苯与(2-氟苯基)乙腈进行类似反应，得到化合物XX作为主要产物；少量得到4-硝基苯甲醚、2-氟-4'-硝基苯基酮（XVIII）和2-氯喹啉-9-碳腈（XXIV）。化合物VII还原为氨基苯基酮衍生物V，经过邻苯二甲酰亚乙酸酰衍生物VI转化为氯代甲基二氮杂西泮II。
• 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。
• Transition-Metal-Free Regiospecific Aroylation of Nitroarenes Using Ethyl Arylacetates at Room Temperature
  作者：Promod Kumar、Anup Kumar Sharma、Tirumaleswararao Guntreddi、Rahul Singh、Krishna Nand Singh

  DOI：10.1021/acs.orglett.7b03882

  日期：2018.2.2

  A novel regiospecific C(sp(3))-C(sp(2)) coupling between ethyl arylacetates and nitroarenes has been developed to deliver biaryl ketones in excellent yields. The protocol is metal-free, mild, and compatible with a number of functional groups on both of the reacting partners.
• Synthesis of Diaryl Ketones Catalyzed by Al₂O₃‐ZrO₂/S₂O₈ ²⁻ Solid Superacid
  作者：Tong‐Shou Jin、Mi‐Na Yang、Guo‐Liang Feng、Tong‐Shuang Li

  DOI：10.1081/scc-120027287

  日期：2004.12.31

  The acylation of a variety of aromatic compounds with benzoyl chloride or its derivatives and catalytic amounts of Al2O3-ZrO2/S2O82- solid superacid affords the corresponding diaryl ketones in good to excellent yields 75-93% at appropriate temperature.