2-(2-氧代-2-苯基乙基)苯甲酸甲酯 | 22129-49-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-(2-氧代-2-苯基乙基)苯甲酸甲酯
• 英文名称: methyl 2-(2-oxo-2-phenylethyl)benzoate
• 英文别名: Methyl 2-phenacylbenzoate；methyl 2-phenacylbenzoate
• CAS: 22129-49-3
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: PXCITKWFJZOGQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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

反应信息

• 作为反应物：
  描述：

  2-(2-氧代-2-苯基乙基)苯甲酸甲酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以95%的产率得到3-phenyl-isocoumarin
  参考文献：
  名称：

  钯催化室温下通过区域选择性 Heck 芳基化由苯乙烯基醚和芳基重氮盐合成 α-芳基苯乙酮

  摘要：

  描述了从苯乙烯基醚和芳基重氮盐制备 α-芳基苯乙酮。该反应在室温下在没有配体和碱的情况下由乙酸钯催化。所开发的方法在反应条件、底物范围、官能团耐受性和产率方面极具吸引力。本方法的合成应用通过从苯乙烯醚制备 α-芳基吲哚和 3-芳基异香豆素来证明。

  DOI：

  10.1039/d1ob01503f
• 作为产物：
  描述：

  高邻苯二甲酸酐 在 三氯化铝 作用下， 以 乙醚 为溶剂， 生成 2-(2-氧代-2-苯基乙基)苯甲酸甲酯
  参考文献：
  名称：

  Reactions proceeding by bicyclic mechanisms

  摘要：

  DOI：

  10.1021/ja01005a034

文献信息

• Pd-Catalyzed/Iodide-Promoted α-Arylation of Ketones for the Regioselective Synthesis of Isocoumarins
  作者：Alessandra Casnati、Raimondo Maggi、Giovanni Maestri、Nicola Della Ca’、Elena Motti

  DOI：10.1021/acs.joc.7b01355

  日期：2017.8.4

  synthesized directly from 2-halobenzoates and ketones through a palladium-catalyzed α-arylation step followed by an intramolecular cyclization process. The addition of iodide anions to the reaction mixture increased yields and selectivities especially when 2-bromobenzoates were employed. This phosphine-free one-pot synthesis features a high functional group tolerance and gives access to richly decorated

  已经通过钯催化的α-芳基化步骤，接着进行分子内环化过程，从2-卤代苯甲酸酯和酮直接合成了多种异香豆素。向反应混合物中加入碘化物阴离子增加了产率和选择性，特别是当使用2-溴苯甲酸酯时。这种无膦的一锅合成功能具有较高的官能团耐受性，可使用装饰精美的异香豆素。这种通用方法成功地完成了具有抗菌和抗真菌活性的重要天然产物木霉素A的全合成。
• Synthesis of 3-Arylisocoumarins by Using Acyl Anion Chemistry and Synthesis of Thunberginol A and Cajanolactone A
  作者：Kasireddy Sudarshan、Manash Kumar Manna、Indrapal Singh Aidhen

  DOI：10.1002/ejoc.201403524

  日期：2015.3

  new strategy for the synthesis of 3-arylisocoumarins and 8-hydroxy-3-arylisocoumarins was investigated by using acyl anion chemistry for the initial C–C bond formation. The obtained keto esters and keto lactones as intermediates underwent based-promoted intramolecular cyclization to afford 3-arylisocoumarins in good yields. The developed methodology was applied for the synthesis of the important natural

  3-芳基异香豆素和8-羟基-3-芳基异香豆素的合成新策略通过使用酰基阴离子化学进行初始C-C键形成研究。得到的酮酯和酮内酯作为中间体进行基于促进的分子内环化，以良好的产率得到3-芳基异香豆素。所开发的方法用于合成重要的天然产物 thunberginol A 和 cajanolactone A。
• A new method using 1,3,5-triazine as an umpolung hydrogen cyanide equivalent toward the syntheses of isoquinolinone and 2-pyridone derivatives
  作者：Joji Hayashida、Shinya Yoshida

  DOI：10.1016/j.tetlet.2018.09.029

  日期：2018.10

  expansion of the synthetic application of 1,3,5-triazine as an umpolung hydrogen cyanide equivalent. The reaction proceeded under mild conditions to provide various isoquinolinone and 2-pyridone derivatives with excellent yields.

  对Hermecz和Hartenstein的环化方法进行了研究。克服了有限的底物范围，从而扩展了1,3,5-三嗪作为umpolung氰化氢等价物的合成应用。反应在温和的条件下进行，以优异的产率提供了各种异喹啉酮和2-吡啶酮衍生物。
• Inhibition of the enzymes in the leukotriene and prostaglandin pathways in inflammation by 3-aryl isocoumarins
  作者：Meera Ramanan、Shweta Sinha、Kasireddy Sudarshan、Indrapal Singh Aidhen、Mukesh Doble

  DOI：10.1016/j.ejmech.2016.08.066

  日期：2016.11

  mPGES1 respectively, play pivotal roles in augmenting inflammatory responses. PGE2 is known to participate in cancer pathological processes as well. Isocoumarins are natural compounds with a wide range of biological activities. In this study, 3-aryl isocoumarin derivatives are synthesized and tested against 5-LOX enzyme in vitro and PGE2 production in HeLa cells. Most of the compounds show high activity

  5-LOX和mPGES1分别在花生四烯酸途径之一中的白三烯和另一途径中的PGE 2的生物合成在增强炎症反应中起关键作用。已知PGE 2也参与癌症病理过程。异香豆素是具有广泛生物活性的天然化合物。在这项研究中，合成了3-芳基异香豆素衍生物，并针对HeLa细胞中的5-LOX酶和体外PGE 2产生进行了测试。大多数化合物显示出高活性，并且1c被鉴定为双重抑制剂，针对5-LOX和PGE 2的IC 50为4.6±0.26μM和6.3±0.13μM。分别生产。另一种化合物7f对5-LOX的IC 50为12.4±0.14μM。进一步的研究表明1c和7f对抗5-LOX的作用机理是混杂的和竞争性的作用方式。Thunberginol A（7c）对PGE 2的生产表现出的IC 50为15.8±0.03μM 。1c和7c抑制mPGES1和COX-2的mRNA表达。这项研究确定了一种具有双重抑制活性的新型支架1c，
• Model Studies Directed toward the Total Synthesis of (±)-Ribasine. A Tandem Cyclization−Cycloaddition Route Leading to the Core Skeleton
  作者：Albert Padwa、Laura Precedo、Mark A. Semones

  DOI：10.1021/jo990136j

  日期：1999.5.1

  A series of alpha-diazo-beta-(o-carbomethoxy)-substituted aryl ketones were prepared and employed as model systems for a synthetic approach toward the alkaloid ribasine. Six-membered ring carbonyl ylide dipoles were generated by treating the diazoketones with a rhodium(II) catalyst. The initially formed dipole was trapped using a variety of dipolarophiles including N-benzylidene methylamine. The Rh(II)-catalyzed behavior of ethyl 2-diazo-3-(2-formylphenyl)-3-oxo-propionate was also studied to probe the chemoselectivity of the reaction. The major products isolated are derived from bimolecular trapping of the carbonyl ylide dipole, as well as intramolecular C-H insertion of the rhodium carbenoid into the aldehydic hydrogen. Changing the catalyst from Rh(II) trifluoroacetate to Rh(II) acetate caused a significant alteration in product distribution. A study of the tandem cyclization-cycloaddition reaction of an o-allyl phenyl substituted diazoketone was also carried out. An unexpected low-temperature intramolecular dipolar cycloaddition of the diazo group across the neighboring pi-bond first occurred, followed by nitrogen extrusion to give products derived from a 1,3-biradical intermediate. By subjecting the diazoketone to the Rh(II) catalyst at 110 degrees C, it was possible to prepare the carbonyl ylide derived cycloadduct in high yield. This result provides good precedent for the future implementation of the cycloaddition strategy toward the synthesis of ribasine.