(2,4-dimethoxyphenyl)(2-hydroxyphenyl)methanone

• 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: (2,4-dimethoxyphenyl)(2-hydroxyphenyl)methanone
• 英文别名: 2,4-Dimethoxy-2'-hydroxybenzophenone；(2,4-dimethoxyphenyl)-(2-hydroxyphenyl)methanone
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: CISHAEPUXMJWEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2,4-dimethoxyphenyl)(2-hydroxyphenyl)methanone 在 吡啶 、 四甲基氢氧化铵 、 氢碘酸 、 苯酚 作用下， 以 水 为溶剂， 反应 44.0h， 生成 西伯尔链接剂
  参考文献：
  名称：

  Antioxidant xanthone derivatives induce cell cycle arrest and apoptosis and enhance cell death induced by cisplatin in NTUB1 cells associated with ROS

  摘要：

  In an effort to develop novel antioxidant as anticancer agents, a series of xanthones were prepared. In vitro screening, the synthetic xanthones revealed significant inhibitory effects on xanthine oxidase and ABTS radical-cation scavenging activity. The selective compounds 2 and 8 induced an accumulation of NTUB1 cells in the G(1) phase arrest and cellular apoptosis by the increase of ROS level. The combination of cisplatin and 2 significantly enhanced the cell death in NTUB1 cells. Compounds 2 and 8 did not show cytotoxic activity in selected concentrations against SV-HUC1 cells. The present results suggested that antioxidants 2 and 8 may be used as anticancer agent for enhancing the therapeutic efficacy of anticancer agents and to reduce their side effect. (c) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.043
• 作为产物：
  描述：

  benzyl 2-(benzyloxy)benzoate 在 正丁基锂 、 5%-palladium/activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 (2,4-dimethoxyphenyl)(2-hydroxyphenyl)methanone
  参考文献：
  名称：

  硫酸铈铵（CAS）介导的苯甲酮的氧化，该苯甲酮具有酚类取代基，用于合成氧杂蒽酮和相关产品

  摘要：

  我们小组先前发表的工作描述了在硫酸铈铵（CAS）介导的反应中，从酚类二苯甲酮合成氧杂蒽酮和相关产物的新方法。在本文中，我们通过对另一组酚二苯甲酮进行CAS反应，以提供一系列化合物，包括x吨，9 H -xanthen-2,9（4a H）-二酮，3 H-螺[苯并呋喃]，来进一步探索这一新颖的反应。-2,1'-环己[2,5]二烯] -3,4'-二酮和联芳基化合物。还对这些反应与更常用的氧化剂硝酸硝酸铈铵（CAN）进行了比较。基于这些结果，已经获得了对反应机理的更深入的了解。另外，合成的黄嘌呤-2,9（4a H描述了通过用连二亚硫酸钠处理生成二氧杂蒽的-二酮。

  DOI：

  10.1021/acs.joc.8b02503

文献信息

• Integrating Metal-Catalyzed C–H and C–O Functionalization To Achieve Sterically Controlled Regioselectivity in Arene Acylation
  作者：Nicholas A. Serratore、Constance B. Anderson、Grant B. Frost、Truong-Giang Hoang、Steven J. Underwood、Philipp M. Gemmel、Melissa A. Hardy、Christopher J. Douglas

  DOI：10.1021/jacs.8b06476

  日期：2018.8.8

  organometallic chemists is the direct functionalization of the bonds most recurrent in organic molecules: C-H, C-C, C-O, and C-N. An even grander challenge is C-C bond formation when both precursors are of this category. Parallel to this is the synthetic goal of achieving reaction selectivity that contrasts with conventional methods. Electrophilic aromatic substitution (EAS) via Friedel-Crafts acylation

  有机金属化学家的一个主要目标是将有机分子中最常见的键直接官能化：CH、CC、CO 和 CN。当两种前体都属于此类时，更大的挑战是 CC 键的形成。与此并行的是实现与传统方法形成对比的反应选择性的合成目标。通过 Friedel-Crafts 酰化的亲电芳香取代 (EAS) 是合成芳基酮的最著名方法，芳基酮是许多药物、农用化学品、香料、染料和其他商品化学品的常见结构基序。然而，只有当所需的酰化位点与反应的电子控制区域选择性一致时，EAS 合成策略才有效。在此，我们报告了空间控制的区域选择性芳烃酰化与水杨酸酯通过铱催化获得明显取代的二苯甲酮。实验和计算数据表明，一种独特的反应机制将 CO 活化和 CH 活化与单一铱催化剂相结合，无需外源氧化剂或碱。我们公开了对芳烃和酯成分的合成范围的广泛探索，最终以简明的合成强效抗癌剂羟基苯司他汀。
• γ-pyrone compounds. IV: Synthesis and antiplatelet effects of mono- and dioxygenated xanthones and xanthonoxypropanolamine
  作者：Chun-Nan Lin、Shorong-Shii Liou、Feng-Nien Ko、Che-Ming Teng

  DOI：10.1002/jps.2600820103

  日期：1993.1

  xanthodilol, 2,3-dihydroxyxanthone diacetate, and 3,4-dihydroxyxanthone and its diacetate showed potent antiplatelet effects on arachidonate- and collagen-induced aggregation. 3,5-Dihydroxyxanthone and its diacetate, 1,6-dimethoxyxanthone, and 3,6-dihydroxyxanthone and its diacetate showed potent antiplatelet effects on arachidonate-induced aggregation.

  由二苯甲酮前体合成黄原醇，单和双氧合的氧杂蒽，以及1,3-，2,3-，3,4-，3,5-，1,6-，2,6-和3,6-二氧合的氧杂蒽由Friedel-Crafts酰化，然后进行碱催化的环化反应以消除甲醇。3-羟-吨酮，黄酮醇，2,3-二羟x吨酮二乙酸盐和3,4-二羟di吨酮及其二乙酸盐对花生四烯酸和胶原诱导的聚集表现出有效的抗血小板作用。3,5-二羟基黄酮及其双乙酸盐，1,6-二甲氧基黄酮和3,6-二羟基黄酮及其二乙酸盐对花生四烯酸诱导的聚集表现出有效的抗血小板作用。
• Synthesis and pharmacological activity of a series of novel xanthone
  申请人：National Science Council

  公开号：US05495005A1

  公开（公告）日：1996-02-27

  A compound, and salts thereof, represented by either formula I or formula II below: (1) Formula I: ##STR1## wherein substituents R.sub.1 -R.sub.7 can be, independently, hydrogen, hydroxy group, C.sub.1-6 alkyl(oxy) group, acetyl ester, or C.sub.1-12 alkyl propanolamine; at least three but no more than four of the substituents are alkyl(oxy) group, hydroxyl group or acetyl ester; no more than one of the substituents can be C.sub.1-12 alkyl propanolamines; R.sub.1, R.sub.3, R.sub.7 cnnnot all be hydroxy groups at the same time; and R.sub.6 is either an hydroxy group or an oxygen-containing glucose. (2) Formula II: ##STR2## wherein substituents R.sub.1 -R.sub.9 can be, indenpendently, hydrogen, hydroxy group and C.sub.1-6 alkyl(oxy) group; and no more then four of the substituents can be methoxy group, hydroxy group, or acetyl ester. These compounds were tested to be capable of inhibiting platelet aggregation, atrioventricular conduction, and calcium influx in myocardiac cells.

  以下是公式I或公式II所代表的化合物及其盐：（1）公式I：其中取代基R.sub.1 -R.sub.7可以独立地是氢、羟基、C.sub.1-6烷基（氧）基、乙酰酯或C.sub.1-12烷基丙醇胺；至少三个但不超过四个取代基是烷基（氧）基、羟基或乙酰酯；不超过一个取代基可以是C.sub.1-12烷基丙醇胺；R.sub.1、R.sub.3、R.sub.7不能同时是羟基；R.sub.6是羟基或含氧葡萄糖。 （2）公式II：其中取代基R.sub.1 -R.sub.9可以独立地是氢、羟基和C.sub.1-6烷基（氧）基；不超过四个取代基可以是甲氧基、羟基或乙酰酯。 这些化合物经测试表明能够抑制血小板聚集、房室传导和心肌细胞内的钙通道。
• Compounds for the treatment of hepatoma
  申请人：National Science Council

  公开号：US05741813A1

  公开（公告）日：1998-04-21

  Compounds of general Formula I in which the substituents of R.sub.1 -R.sub.7 are hydrogen, hydroxy group, C.sub.1-6 alkyl group, C.sub.1-6 alkoxy group, or epoxypropoxy, but at the most, six of the substituents can simultaneously be hydrogen, methoxy group, or hydroxy group, or epoxypropoxy group for activity against hepatoma. There are also described processes for the preparation of the novel compounds and useful intermediates. Substitute benzophenones are described.

  通式I的化合物中，R.sub.1-R.sub.7的取代基为氢、羟基、C.sub.1-6烷基、C.sub.1-6烷氧基或环氧丙氧基，但最多只有六个取代基可以同时为氢、甲氧基或羟基，或环氧丙氧基，以用于肝癌的活性。还描述了制备新化合物和有用中间体的过程。还描述了取代苯酮。
• Rh(III)-catalyzed aldehyde C–H bond functionalization of salicylaldehydes with arylboronic acids
  作者：Dahai Wang、Sunliang Cui

  DOI：10.1016/j.tet.2015.09.053

  日期：2015.11

  A Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids has been developed, with features of mild reaction condition and high efficiency. Furthermore, the functionalized 2-hydroxybenzophenone could be subject to divergent synthesis of heterocycles. (C) 2015 Elsevier Ltd. All rights reserved.