(3-nitrophenyl)(p-tolyl)methanone | 71319-21-6

• 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: (3-nitrophenyl)(p-tolyl)methanone
• 英文别名: 3-nitro-4'-methylbenzophenone；(4-Methylphenyl)-(3-nitrophenyl)methanone
• CAS: 71319-21-6
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: GTPDCZXPNKYFHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  (3-nitrophenyl)(p-tolyl)methanone 在 硫酸 、 硝酸 作用下， 生成 4-methyl-3,5,3'-trinitro-benzophenone
  参考文献：
  名称：

  Blakey; Scarborough, Journal of the Chemical Society, 1928, p. 2492

  摘要：

  DOI：
• 作为产物：
  描述：

  1-nitro-3-(nitro(p-tolyl)methyl)benzene 在 disodium hydrogenphosphate 、 sodium hydroxide 、 Oxone 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.5h， 以29.7 mg的产率得到(3-nitrophenyl)(p-tolyl)methanone
  参考文献：
  名称：

  Palladium-Catalyzed α-Arylation of Aryl Nitromethanes

  摘要：

  Catalytic conditions for the alpha-arylation of aryl nitromethanes have been discovered using parallel microscale experimentation, despite two prior reports of the lack of reactivity of these aryl nitromethane precursors. The method efficiently provides a variety of substituted, isolable diaryl nitromethanes. In addition, it is possible to sequentially append two different aryl groups to nitromethane. Mild oxidation conditions were identified to afford the corresponding benzophenones via the Nef reaction, and reduction conditions were optimized to afford several diaryl methylamines.

  DOI：

  10.1021/acs.orglett.5b02793

文献信息

• Cyclobutene derivatives, their preparation and their therapeutic uses
  申请人：Sankyo Company, Limited

  公开号：US06329405B1

  公开（公告）日：2001-12-11

  Compounds of formula (I): {wherein: R1 and R2 each represents a variety of organic groups; R3 and R4 each represents hydrogen or a variety of organic groups; A represents a group of formula (A-1): [wherein: R5 represents hydrogen, hydroxy or alkyl, R6 represents hydroxy, alkoxy, alkylthio or an amine residue, X and Y each represents oxygen or sulfur, and Z represents a direct single bond between the nitrogen atom shown and the benzene ring shown in formula (I), or an alkylene group], G represents a single bond, alkylene or substituted alkylene; the broken line represents a single or double bond; when the broken line represents a double bond, D represents a carbon atom; and E represents an ═N—O— group; when the broken line represents a single bond, D represents a CH group or a nitrogen atom, and E represents an oxygen atom, a sulfur atom, an —NH— group or a —CO— group}; and pharmaceutically acceptable salts, esters or other derivatives thereof have the ability to inhibit an ileal bile transporter and so may be used to treat or prevent hypercholesterolemia.

  式(I)的化合物： 其中：R1和R2分别代表各种有机基团；R3和R4分别代表氢或各种有机基团；A代表式(A-1)的基团： [其中：R5代表氢、羟基或烷基，R6代表羟基、烷氧基、烷基硫氧基或胺基残基，X和Y分别代表氧或硫，Z代表氮原子与式(I)中所示苯环之间的直接单键，或者是一个烷基链]， G代表单键、烷基或取代烷基；虚线代表单键或双键；当虚线代表双键时，D代表碳原子；E代表一个-N—O—基团；当虚线代表单键时，D代表一个CH基团或一个氮原子，E代表一个氧原子、硫原子、一个—NH—基团或一个—CO—基团；以及药学上可接受的盐、酯或其他衍生物具有抑制回肠胆汁转运蛋白的能力，因此可用于治疗或预防高胆固醇血症。
• Pd‐NHC catalysed Carbonylative Suzuki coupling reaction and its application towards the synthesis of biologically active 3‐aroylquinolin‐4 (1<i>H</i>)‐one and acridone scaffolds
  作者：Prasanjit Ghosh、Bhaskar Ganguly、Sajal Das

  DOI：10.1002/aoc.4173

  日期：2018.3

  We have unfolded a convenient and mild protocol for the synthesis of diaryl ketones via Pd‐ NHC catalysed carbonylative Suzuki coupling reaction. Notably, this method offers advantages like no use of toxic CO gas, shorter reaction time, high yield, and broad substrate scope. Several sensitive functional groups (like‐COMe, ‐COOMe, ‐F, ‐Cl, ‐Br, ‐NH2, ‐CN) are well tolerated in this reaction. In addition

  我们已经展示了通过Pd-NHC催化的羰基化Suzuki偶联反应合成二芳基酮的便捷，温和的方法。值得注意的是，该方法具有以下优点：不使用有毒的CO气体，较短的反应时间，高收率和广泛的底物范围。在该反应中对几个敏感的官能团（如COMe，-COOMe，-F，-Cl，-Br，-NH 2，-CN）具有良好的耐受性。此外，我们还展示了一种新的合成生物活性和药学上重要的2-取代的3-Aroylquinolin-4（1 H）-one和acridone支架的有效途径。
• Synthesis of unsymmetric ketones via ligandless Pd-catalyzed reaction of acyl chlorides with organoboranes
  作者：Nikolay A. Bumagin、Dmitriy N. Korolev

  DOI：10.1016/s0040-4039(99)00364-0

  日期：1999.4

  The cross-coupling reaction of sodium tetra-arylborates with acyl chlorides to give high yields of unsymmetric ketones has been carried out at 20°C in the presence of Pd(OAc)2 and Na2CO3 in dry or aqueous acetone. Under aqueous conditions arylboronic acids react smoothly with benzoyl chloride resulting in substituted benzophenones.

  四芳基硼酸钠与酰氯的交叉偶联反应产生高产率的不对称酮，已在干燥或含水丙酮中，在Pd（OAc）2和Na 2 CO 3存在下于20°C进行。在水性条件下，芳基硼酸与苯甲酰氯平稳反应，生成取代的二苯甲酮。
• Palladium-catalyzed reactions of arylboron compounds with carboxylic acid chlorides
  作者：D. N. Korolev、N. A. Bumagin

  DOI：10.1023/b:rucb.0000030812.95602.0a

  日期：2004.2

  Reactions of sodium tetraarylborates and arylboronic acids with acyl chlorides in the presence of palladium salts afford non-symmetrical ketones in high yields under mild conditions.

  四芳基硼酸钠和芳基硼酸与酰氯在钯盐存在下的反应在温和条件下以高产率提供非对称酮。
• Antimony(V) Chloride-Benzyltriethylammonium Chloride Complex as an Efficient Catalyst for Friedel−Crafts Acylation Reactions
  作者：An-ping Huang、Xue-yuan Liu、Lian-hua Li、Xiao-li Wu、Wei-min Liu、Yong-min Liang

  DOI：10.1002/adsc.200303233

  日期：2004.5

  A novel catalytic system, the complex of antimony(V) chloride (SbCl5) and benzyltriethylammonium chloride (TEBA), C6H5CH2NEt3(SbCl5)2Cl complex, is described for Friedel–Crafts acylation reactions of aromatics with acyl and sulfonyl chlorides. The catalyst has a number of useful characteristics, such as ready access, minimal toxicity, reusability, insensitivity to atmosphere and moisture, rapid acylation

  一种新的催化体系，该复合物的锑（V），氯化锑酸盐（SbCl 5）和苄基三乙基氯化铵（TEBA），C 6 H ^ 5 CH 2净3酸盐（SbCl 5）2 C1复合物，芳烃的Friedel-Crafts酰化反应进行说明与酰基和磺酰氯。该催化剂具有许多有用的特性，例如易于获得，毒性最小，可重复使用，对大气和湿气不敏感，以高收率快速酰化以及易于操作。