4-(2-oxo-2-phenylethoxy)-2H-chromen-2-one | 81263-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-oxo-2-phenylethoxy)-2H-chromen-2-one
• 英文别名: 4-(2-oxo-2-phenylethoxy)-2H-1-benzopyran-2-one；4-phenacyloxychromen-2-one
• CAS: 81263-52-7
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: SNHRPWBRXQFXNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-oxo-2-phenylethoxy)-2H-chromen-2-one 在 硫酸 、 sodium azide 作用下， 反应 1.17h， 以71%的产率得到2-(2-oxo-2H-chromen-4-yloxy)-N-phenylacetamide
  参考文献：
  名称：

  Novel oxime-bearing coumarin derivatives act as potent Nrf2/ARE activators in vitro and in mouse model

  摘要：

  We have designed and synthesized certain novel oxime- and amide-bearing coumarin derivatives as nuclear factor erythroid 2 p45-related factor 2 (Nrf2) activators. The potency of these compounds was measured by antioxidant responsive element (ARE)-driven luciferase activity, level of Nrf2-related cytoprotective genes and proteins, and antioxidant activity. Among them, (Z)-3-(2-(hydroxyimino)-2-phenylethoxy)-2H-chromen-2-one (17a) was the most active, and more potent than the positive t-BHQ in the induction of ARE-driven luciferase activity. Exposure of HSC-3 cells to various concentrations of 17a strongly increased Nrf2 nuclear translocation and the expression level of Nrf2-mediated cytoprotective proteins in a concentration-dependent manner. HSC-3 cells pretreated with 17a significantly reduced t-BOOH-induced oxidative stress. In the animal experiment, Nrf2-mediated cytoprotective proteins, such as aldo-keto reductase 1 subunit C-1 (AKR1C1), glutathione reductase (GR), and heme oxygenase (HO-1), were obviously elevated in the liver of 17a-treated mice than that of control. These results suggested that novel oxime-bearing coumarin 17a is able to activate Nrf2/ARE pathway in vivo and are therefore seen as a promising candidate for further investigation. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.029
• 作为产物：
  描述：

  4-羟基香豆素 、 1-phenyl-2-(p-tolylsulfonyloxy)ethanone 在 ammonium acetate 、 溶剂黄146 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 3.0h， 以78.5%的产率得到4-(2-oxo-2-phenylethoxy)-2H-chromen-2-one
  参考文献：
  名称：

  有机合成中的[羟基（甲苯磺酰氧基）碘]苯：使用α-甲苯磺酰氧基酮轻松合成呋喃[3,2-c]香豆素

  摘要：

  摘要 描述了通过 4-羟基香豆素和 α-甲苯磺酰氧基酮 (1a-g) 的环缩合轻松合成呋喃 [3,2-c] 香豆素 (2a-g)。提出了一种可能的机制，包括 CC 键形成，然后是 5-exo-tet 环化。图形概要

  DOI：

  10.1080/00397911.2011.570471

文献信息

• Antineoplastic .alpha.-methylene-.gamma.-butyrolactones
  申请人：National Science Council (Taiwan)

  公开号：US05962460A1

  公开（公告）日：1999-10-05

  The present invention provides antineoplastic .alpha.-methylene-.gamma.-butyrolactones represented by the general formula \x9bI! wherein R.sub.1 is a phenyl group optionally substituted with one or two groups selected from the group consisting of halide, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, phenyl, nitro and amino;.sub.2 R represents hydrogen, halide, (C.sub.1 -C.sub.4)alkyl or benzyl; X represents N; or wherein R.sub.1 is a phenyl group optionally substituted with one or two groups selected from the group consisting of halide, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4) alkoxy, nitro and amino; R.sub.2 represents Cl, F, or benzyl; X represents CH. These .alpha.-methylene-.gamma.-butyrolactones may be administered with an inert diluent or with a pharmaceutically acceptable carrier in controlling the growth of a neoplasm in a patient afflicted with a neoplasm disease. ##STR1##

  本发明提供了一种抗肿瘤的α-亚甲基-γ-丁内酯，其通式表示为\x9bI!其中R.sub.1是一个苯基，可选地取代为卤素、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)烷氧基、苯基、硝基和氨基中的一种或两种基团；R代表氢、卤素、(C.sub.1 -C.sub.4)烷基或苄基；X代表N；或其中R.sub.1是一个苯基，可选地取代为卤素、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)烷氧基、硝基和氨基中的一种或两种基团；R.sub.2代表Cl、F或苄基；X代表CH。这些α-亚甲基-γ-丁内酯可以与惰性稀释剂或药用可接受的载体一起使用，以控制患有肿瘤疾病的患者体内肿瘤的生长。
• .alpha.-methylene-.gamma.-butyrolactones: new inhibitors of platelet
  申请人：National Science Council

  公开号：US05646164A1

  公开（公告）日：1997-07-08

  The present inventors have discovered three classes of novel .alpha.-methylene-.gamma.-butyrolactones with excellent antiplatelet activity. As a result of intensive studies, it has been found that compounds represented by the formula I-III are potent inhibitors of platelet aggregation. ##STR1## For the formula I, R.sub.1 is a methyl, a phenyl group optionally substituted with one or two group selected from halide, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, phenyl, nitro, amino. For the formula II, R.sub.1 is a methyl, a phenyl group optionally substituted with one or two group selected from halide, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, phenyl, nitro, amino; R.sub.2 represents hydrogen, halide, (C.sub.1 -C.sub.4) alkyl, phenyl, nitro, amino; R.sub.3 represents hydrogen, halide, (C.sub.1 -C.sub.4) alkyl, phenyl, nitro, amino. For the formula III, R.sub.1 is a methyl, a phenyl group optionally substituted with one or two group selected from halide, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, phenyl, nitro, amino; R.sub.4 represents hydrogen, hydroxy, (C.sub.1 -C.sub.4) alkyl. The present invention also provides a cost-efficient method for the preparation of formula I-III. Formula I-III may be administered orally or parenterly with an inert diluent or with a pharmaceutically acceptable carrier in the treatment or the prevention of cardiovascular disease.

  目前的发明者发现了三类具有出色抗血小板活性的新型α-亚甲基-γ-丁酸内酯。经过深入研究发现，由I-III式表示的化合物是有效的血小板聚集抑制剂。对于式I，R.sub.1是一个甲基，一个苯基，可选择地取代为卤素、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)氧烷基、苯基、硝基、氨基中的一个或两个基团。对于式II，R.sub.1是一个甲基，一个苯基，可选择地取代为卤素、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)氧烷基、苯基、硝基、氨基中的一个或两个基团；R.sub.2代表氢、卤素、(C.sub.1 -C.sub.4)烷基、苯基、硝基、氨基；R.sub.3代表氢、卤素、(C.sub.1 -C.sub.4)烷基、苯基、硝基、氨基。对于式III，R.sub.1是一个甲基，一个苯基，可选择地取代为卤素、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)氧烷基、苯基、硝基、氨基中的一个或两个基团；R.sub.4代表氢、羟基、(C.sub.1 -C.sub.4)烷基。本发明还提供了一种成本效益高的制备I-III式的方法。I-III式可以通过口服或肌注与惰性稀释剂或药用载体一起使用，用于治疗或预防心血管疾病。
• Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent
  作者：Zhanwei Ma、Min Zhou、Lin Ma、Min Zhang

  DOI：10.1177/1747519820907244

  日期：2020.7

  acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare

  由伊顿试剂（五氧化二磷-甲磺酸）促进的 α-苯氧基酮的环脱水用于在温和条件下以中等至优异的产率制备 3-取代或 2,3-二取代的苯并呋喃。该方法提供了从容易获得的起始材料（如苯酚和 α-溴酮）中轻松获得苯并呋喃的途径。反应效率高，这归功于伊顿试剂良好的反应性和流动性。该反应可用于制备萘并呋喃香豆素、苯并噻吩和苯并吡喃。
• Metal-Free Synthesis of Furocoumarins: An Approach via Iodine-Promoted One-Pot Cyclization between 4-Hydroxycoumarins and Acetophenones
  作者：Phuc H. Pham、Que T. D. Nguyen、Nhu K. Q. Tran、Vu H. H. Nguyen、Son. H. Doan、Hiep Q. Ha、Thanh Truong、Nam T. S. Phan

  DOI：10.1002/ejoc.201800983

  日期：2018.8.31

  An iodine‐mediated one‐pot synthesis of furocoumarins has been developed. The furocoumarins were obtained in high yields in the presence of NH4OAc as an additive, whereas neither acidic nor basic additives were effective.

  已经开发了碘介导的呋喃香豆素的一锅法合成法。在存在NH 4 OAc作为添加剂的情况下，以高收率获得了呋喃香豆素，而酸性和碱性添加剂均无效。
• Synthesis of Coumarin Derivatives as Inhibitors of Platelet Aggregation
  作者：Yeh-Long Chen、Tai-Chi Wang、Kuan-Han Lee、Cherng-Chyi Tzeng、Ya-Ling Chang、Che-Ming Teng

  DOI：10.1002/hlca.19960790308

  日期：1996.5.8

  In a search for the inhibitors of platelet aggregation, certain coumarin derivatives were synthesized and evaluated for antiplatelet activity against thrombin(Thr)-, arachidonic acid(AA)-, collagen(Col)-, and platelet-activating-factor(PAF)-induced aggregation in washed rabbit platelets. These compounds were synthesized from 4-hydroxycoumarin (1) or naphthalen-1-ol via alkylation and Reformatsky-type

  在寻找血小板聚集抑制剂时，合成了某些香豆素衍生物并评估了其对凝血酶（Thr）-，花生四烯酸（AA）-，胶原蛋白（Col）-和血小板活化因子（PAF）-的抗血小板活性。在洗涤的兔血小板中诱导聚集。这些化合物是由4-羟基香豆素（1）或萘-1-醇经烷基化和Reformatsky型缩合反应合成的（图1-3）。其中，显示了4-[（（2,3,4,5-四氢-4-亚甲基-5-氧代-2-苯基呋喃-2-基）甲氧基] -2 H -1-苯并吡喃-2-酮（6b）IC 50对AA和PAF诱导的聚集产生有效的抗血小板作用值分别为8.21和103.67m̈M（见表1和2）。通过在内酯环的2-苯基上引入适当的取代基，可以进一步提高6b对PAF诱导的聚集的抗血小板效力。