乙基4-苯甲酰基苯甲酸酯 | 15165-27-2

• 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: 乙基4-苯甲酰基苯甲酸酯
• 中文别名: 乙基4-苯甲酰苯酸酯
• 英文名称: ethyl 4-benzoylbenzoate
• 英文别名: 4-ethoxycarbonylbenzophenone
• CAS: 15165-27-2
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: OTYJRBJRMVNCQV-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  226-227 °C(Press: 13 Torr)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  乙基4-苯甲酰基苯甲酸酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 [4-(羟甲基)苯基]-苯基甲酮
  参考文献：
  名称：

  Imidazopyridine-fused [1,3]diazepinones: modulations of positions 2 to 4 and their impacts on the anti-melanoma activity

  摘要：

  A series of 19 novel pyrido-imidazodiazepinones, with modulations of positions 2, 3 and 4 of the diazepine ring were synthesised and screened for their in vitro cytotoxic activities against two melanoma cell lines (A375 and MDA-MB-435) and for their potential toxicity against NIH-3T3 non-cancerous cells. Selected compounds were also evaluated on the NCI-60 cell line panel. The SAR study revealed that the molecular volume and the cLogP of compounds modified at position 2 were significantly correlated with the activity of these compounds on melanoma cell lines. Moreover, introduction of a heterocyclic group at position 2 or an azido-alkyl chain at position 4 led to compounds displaying a significantly different activity profile on the NCI-60 cell line panel, compared to phenyl-substituted compounds at position 2 of the diazepinone. This study provides us crucial information for the development of new derivatives active against melanoma.

  DOI：

  10.1080/14756366.2020.1748024
• 作为产物：
  描述：

  MIDA alkenyl-2-boronate 在 sodium periodate 、 四氧化锇 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 、 N-甲基吗啉氧化物 作用下， 以 aq. phosphate buffer 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 0.58h， 生成 乙基4-苯甲酰基苯甲酸酯
  参考文献：
  名称：

  Suzuki coupling of aroyl-MIDA boronate esters – A preliminary report on scope and limitations

  摘要：

  DOI：

  10.1016/j.tetlet.2021.153147

文献信息

• Cobalt carbonyl as an effective CO source in one-pot synthesis of esters from aryl halides
  作者：P. Baburajan、R. Senthilkumaran、Kuppanagounder P. Elango

  DOI：10.1039/c3nj00548h

  日期：——

  For the first time, we have successfully applied Co2(CO)8 as an effective carbonyl source for the Pd catalysed alkoxycarbonylation of aryl halides affording the corresponding aryl esters under mild microwave conditions. A wide variety of esters and carbonyl derivatives were prepared using this protocol.

  首次成功地将Co2(CO)8作为有效的羰基源用于Pd催化下温和微波条件中的芳基卤化物的烷氧羰基化反应，合成了相应的芳基酯。利用这一方案，制备了多种酯和羰基衍生物。
• A convenient method for the preparation of aromatic ketones from acyl chlorides and arylzinc bromides using a cobalt catalysis
  作者：Hyacinthe Fillon、Corinne Gosmini、Jacques Périchon

  DOI：10.1016/j.tet.2003.08.032

  日期：2003.10

  Aromatic ketones are synthesized efficiently via cobalt catalyzed cross-coupling reaction between arylzinc bromides and acid chlorides. Arylzinc bromides prepared chemically via a cobalt catalysis undergo coupling without additional catalyst unlike their electrochemical analogs.

  通过芳基溴化锌与酰氯之间的钴催化交叉偶联反应，可以有效地合成芳族酮。与钴的电化学类似物不同，通过钴催化化学制备的芳基溴化锌无需额外的催化剂即可偶联。
• SELECTIVE REDUCTION WITH LITHIUM ALUMINUM HYDRIDE/DIPHOSPHORUS TETRAIODIDE. A MILD CONVERSION OF AROMATIC KETONES TO PARENT HYDROCARBONS
  作者：Hitomi Suzuki、Reiko Masuda、Hirohisa Kubota、Atsuhiro Osuka

  DOI：10.1246/cl.1983.909

  日期：1983.6.5

  Treatment of aromatic ketones with the title reagent in boiling benzene gives parent hydrocarbons in good to moderate yields.

  在沸腾的苯中用标题试剂处理芳族酮得到良好至中等产率的母体烃。
• Room-Temperature Decarboxylative Couplings of α-Oxocarboxylates with Aryl Halides by Merging Photoredox with Palladium Catalysis
  作者：Wan-Min Cheng、Rui Shang、Hai-Zhu Yu、Yao Fu

  DOI：10.1002/chem.201502286

  日期：2015.9.14

  Enabled by merging iridium photoredox catalysis and palladium catalysis, α‐oxocarboxylate salts can be decarboxylatively coupled with aryl halides to generate aromatic ketones and amides at room temperature. DFT calculations suggest that this reaction proceeds through a Pd0–PdII–PdIII pathway, in which the PdIII intermediate is responsible for reoxidizing IrII to complete the IrIII–*IrIII–IrII photoredox

  通过合并铱的光氧化还原催化和钯催化，α-氧代羧酸盐可以与芳基卤化物脱羧偶联，在室温下生成芳族酮和酰胺。DFT计算表明，该反应通过Pd 0 -Pd II -Pd III途径进行，其中Pd III中间体负责重新氧化Ir II以完成Ir III- * Ir III -Ir II光氧化还原循环。
• Convenient Processes for the Synthesis of Aromatic Ketones from Aryl Bromides and Carboxylic Anhydrides Using a Cobalt Catalysis
  作者：Igor Kazmierski、Mylène Bastienne、Corinne Gosmini、Jean-Marc Paris、Jacques Périchon

  DOI：10.1021/jo0352169

  日期：2004.2.1

  various para- and meta-substituted aromatic bromides, mostly bearing sensitive moieties, with several carboxylic acid anhydrides is reported. This reaction can be carried out in two steps, by forming an aromatic organozinc reagent via cobalt catalysis in the first step, or even more interestingly in a single step, also by using a cobalt-based catalyst. The aromatic ketones are obtained by these new, mild

  据报道，大多数具有敏感部分的各种对位和间位取代的芳族溴化物与几种羧酸酐的交叉偶联。该反应可以通过两步进行，通过在第一步中通过钴催化形成芳族有机锌试剂，或者甚至更有趣地是在一步中，也可以通过使用钴基催化剂来进行。通过这些新的，温和且方便的方法，与起始的芳基溴化物相比，芳族酮的收率为30-79％。还公开了结果，表明钴物种在有机锌试剂与亲电试剂的偶联中所起的作用可能与更常见的过渡金属配合物相似。