(2-chloro-4-nitrophenyl)(phenyl)methanone | 33663-73-9

• 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-chloro-4-nitrophenyl)(phenyl)methanone
• 英文别名: (2-Chlor-4-nitrophenyl)phenylketon；2-chloro-4-nitrobenzophenone；2-chloro-5-nitrobenzophenone；2-Chlor-4-nitrobenzophenbenzoesaeure；(2-chloro-4-nitrophenyl)-phenylmethanone
• CAS: 33663-73-9
• 化学式: C₁₃H₈ClNO₃
• 分子量: 261.664
• InChiKey: PGIPTXFXNUVZFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C (decomp)
• 沸点：
  411.9±30.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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

反应信息

• 作为反应物：
  描述：

  (2-chloro-4-nitrophenyl)(phenyl)methanone 在 potassium tert-butylate 、 tin(ll) chloride 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成 [4-(2-Amino-phenylamino)-2-chloro-phenyl]-phenyl-methanone
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of Aminobenzophenones. A Novel Class of p38 MAP Kinase Inhibitors with High Antiinflammatory Activity

  摘要：

  We wish to report the synthesis and structure-activity relationship (SAR) of a series of 4-aminobenzophenones, as a novel compound class with high antiinflammatory activity. Our initial lead, {4-[(2-aminophenyl)amino]phenyl}(phenyl)methanone (3), was systematically optimized and resulted in compounds that potently inhibited the release of the proinflammatory cytokines IL-1beta and TNF-alpha in human peripheral blood mononuclear cells stimulated by LPS. One of the most potent compounds, among others, was {4-[(2-aminophenyl)amino]-2-chlorophenyl}(2-methylphenyl)methanone (45) with IC50 values of 14 and 6 nM for the inhibition of IL-1beta and TNF-alpha, respectively. Furthermore, we found these types of compounds to be potent and selective p38 MAP kinase inhibitors, e.g. 45 had an IC50 value of 10 nM. Molecular modeling was used to rationalize our SAR data and to propose a model for the interaction of compound 45 with the p38 MAP kinase. The model involved a favorable hydrogen bond between the carbonyl group of the benzophenone and the NH of Met-109, positioning ring A in the hydrophobic pocket I of the enzyme. Good antiinflammatory effects were demonstrated in two murine models of dermatitis after topical application (oxazolone and TPA model).

  DOI：

  10.1021/jm030851s
• 作为产物：
  描述：

  2-氯-4-硝基苯甲酸 在 4-二甲氨基吡啶 、 potassium phosphate 、 Pd/α-Al2O3 、 钯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 (2-chloro-4-nitrophenyl)(phenyl)methanone
  参考文献：
  名称：

  通过化学选择性 C(酰基)-O 键激活杂芳基酯的异质 Suzuki-Miyaura 偶联†

  摘要：

  开发了一种以杂芳基酯和芳基硼酸为偶联伙伴的位点选择性负载钯纳米颗粒催化的 Suzuki-Miyaura 交叉偶联反应。该方法通过成功抑制不需要的脱羰现象，通过酯的 C(酰基)-O 键活化，为芳基酮的形成提供了一种多相催化途径。该催化剂可重复使用，并在八次循环后表现出较高的活性。反应前后催化剂的XPS分析表明该反应可能是通过以Pd 0开始的Pd 0 /Pd II催化循环进行的。

  DOI：

  10.1039/c9ra02394a

文献信息

• 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。
• Benzophenone ureas and method for utilizing the same
  申请人：American Cyanamid Company

  公开号：US03988300A1

  公开（公告）日：1976-10-26

  This invention provides for novel benzophenone ureas, a method for preparing the same, and a method for controlling undesirable broadleaf weeds and grasses therewith, wherein said benzophenone is represented by the generic formula: ##SPC1## Where A and B each represent hydrogen, methyl, halogen, trifluoromethyl, or methoxy; R.sub.1 and R.sub.2 are taken singly or in combination and represent hydrogen, lower alkyl, alkoxy, alkoxyalkyl, cycloalkyl, cyclohetero, loweralkylamino, lower alkenyl or lower alkynyl, with the proviso that A is either meta or para to the --HN--CO--NR.sub.1 R.sub.2 substituent.

  这项发明提供了新型苯酮脲类化合物，以及其制备方法和用于控制不良的阔叶杂草和禾本科植物的方法，其中所述苯酮脲类化合物由通用式表示：##SPC1## 其中A和B分别表示氢、甲基、卤素、三氟甲基或甲氧基；R.sub.1和R.sub.2单独或组合表示氢、低碳基、烷氧基、烷氧基烷基、环烷基、环杂环烷基、低碳基氨基、低烯基或低炔基，但A必须是--HN--CO--NR.sub.1 R.sub.2 取代基的间位或对位。
• Mandelic Acid as Synthetic Equivalent of Benzoyl Carbanion. Synthesis of Nitrobenzophenones
  作者：José R. Pedro、Gonzalo Blay、Luz Cardona、Isabel Fernández、Raquel Michelena、Teresa Ramírez、Rafael Ruiz-García

  DOI：10.1055/s-2003-42123

  日期：——

  p-fluoronitrobenzenes, followed by hydrolysis of theacetal moiety and oxidative decarboxylation of the resulting α-hydroxyacids. The whole sequence involves the use of mandelic acid as synthetic equivalent of the benzoyl carbanion.

  硝基二苯甲酮由扁桃酸二氧戊环制备。该序列开始于二氧戊环酮的烯醇化物在对氟硝基苯上的芳香亲核取代，然后是缩醛部分的水解和所得α-羟基酸的氧化脱羧。整个序列涉及使用扁桃酸作为苯甲酰基碳负离子的合成等价物。
• Highly Diastereoselective Arylation of (<i>S</i>)-Mandelic Acid Enolate:  Enantioselective Synthesis of Substituted (<i>R</i>)-3-Hydroxy-3-phenyloxindoles and (<i>R</i>)-Benzylic Acids and Synthesis of Nitrobenzophenones
  作者：Santiago Barroso、Gonzalo Blay、Luz Cardona、Isabel Fernández、Begoña García、José R. Pedro

  DOI：10.1021/jo0402069

  日期：2004.10.1

  leads directly to enantiomerically pure (R)-3-hydroxy-3-phenyloxindoles. On the other hand the basic hydrolysis of the dioxolanone moiety in all the arylation products (ortho and para) leads to enantiomerically pure substituted (R)-benzylic acids. The oxidative decarboxylation of these latter with oxygen as terminal oxidant in the presence of pivalaldehyde and the Co(III)-Me2opba complex as catalyst gives

  描述了容易获得的取代的（R）-3-羟基-3-苯基氧吲哚，（R）-苯甲酸和二苯甲酮。衍生自旋光性（S）-扁桃酸和新戊醛的（2 S，5 S）-顺式-1,3-二氧戊环-4-一的烯醇锂与数个邻卤和对卤硝基苯的反应易于进行得到具有良好收率和非对映选择性的相应芳基化产物。邻位用Zn / HCl / EtOH还原硝基-硝基芳基化产物与二氧戊环部分的分子内氨基分解反应直接导致对映体纯的（R）-3-羟基-3-苯基氧吲哚。另一方面，所有芳基化产物（正和对位）中二氧戊环酮部分的碱性水解导致对映体纯的取代的（R）-苯甲酸。在新戊醛和Co（III）-Me 2 opba络合物作为催化剂的存在下，用氧作为末端氧化剂，将后者氧化脱羧，得到取代的硝基二苯甲酮。
• Novel benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
  申请人：G.D. Searle & Co.

  公开号：US20020013476A1

  公开（公告）日：2002-01-31

  Provided are novel benzothiepines, derivatives, and analogs thereof; pharmaceutical compositions containing them; and methods of using these compounds and compositions in medicine, particularly in the prophylaxis and treatment of hyperlipidemic conditions such as those associated with atherosclerosis or hypercholesterolemia, in mammals.

  提供了新型苯并噻吩类化合物及其衍生物和类似物；含有它们的药物组合物；以及在医学中使用这些化合物和组合物的方法，特别是在哺乳动物中预防和治疗高脂血症状，如与动脉粥样硬化或高胆固醇血症相关的情况。