1-[2,4-dihydroxy-3,5-bis-(3-methyl-but-2-enyl)-phenyl]-ethanone | 24672-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2,4-dihydroxy-3,5-bis-(3-methyl-but-2-enyl)-phenyl]-ethanone
• 英文别名: 1-(2,4-dihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl)ethanone；1-[2,4-dihydroxy-3,5-bis-(3-methylbut-2-enyl)phenyl]ethanone；1-[2,4-dihydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]ethanone；3,5-bis(3,3-dimethylallyl)-2,4-dihydroxy-acetophenone；2,4-dihydroxy-3,5-diprenylacetophenone；3,5-di-C-prenylresacetophenone
• CAS: 24672-82-0
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: DVZGZERRGSOKDB-UHFFFAOYSA-N

物化性质

• 熔点：
  117°C
• 沸点：
  455.0±45.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[2,4-dihydroxy-3,5-bis-(3-methyl-but-2-enyl)-phenyl]-ethanone 在 四(三苯基膦)钯 、 potassium carbonate 、 caesium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 (E)-1-(2,4-dihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  天然存在的烯丙基化和吡喃并邻苯二酚作为强效抗炎药的合成和药理特性

  摘要：

  摘要已开发出一种有效的方法来合成天然存在的烯丙基查耳酮。坎佐诺尔C（1），链球菌素（2），Crotaorixin（3），药物元素素（4），利加格查尔酮A（5）和Abyssinone D（6）以及吡喃丙酮副棕榈素C（7），蒽醌（8）和3- O。 -甲基杜鹃花A（9）。合成的关键步骤是克莱森-施密特缩合反应。随后，在脂多糖（LPS）诱导的RAW-264.7巨噬细胞中研究了它们的抗炎作用。在合成的查耳酮中，化合物5（IC 50 = 10.41μmol/ L），化合物6（IC 50 = 9.65μmol/ L）和化合物8（IC 50 = 15.34μmol/ L）表现出显着的活性，没有细胞毒性。化合物9（IC 50 = 4.5μmol/ L）表现出最大（83.6％）一氧化氮（NO）抑制作用，但显示出轻微的细胞毒性。

  DOI：

  10.1016/j.cclet.2016.01.043
• 作为产物：
  描述：

  C₂₂H₂₈O₅ 在 水 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以94%的产率得到1-[2,4-dihydroxy-3,5-bis-(3-methyl-but-2-enyl)-phenyl]-ethanone
  参考文献：
  名称：

  NaOAc-Mediated Selective Deprotection of Aromatic Acetates and Its Application in the Synthesis of Natural Products

  摘要：

  We have developed an efficient method to deacetylate the aromatic acetates using NaOAc in excellent yields and demonstrated the application of the procedure in the synthesis of natural products.

  DOI：

  10.1080/00397910802621731

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• Synthesis and Insight into the Structure–Activity Relationships of Chalcones as Antimalarial Agents
  作者：Narender Tadigoppula、Venkateswarlu Korthikunta、Shweta Gupta、Papireddy Kancharla、Tanvir Khaliq、Awakash Soni、Rajeev Kumar Srivastava、Kumkum Srivastava、Sunil Kumar Puri、Kanumuri Siva Rama Raju、Wahajuddin、Puran Singh Sijwali、Vikash Kumar、Imran Siddiqi Mohammad

  DOI：10.1021/jm300588j

  日期：2013.1.10

  licorice, is the most promising antimalarial compound reported so far. In continuation of our drug discovery program, we isolated two similar chalcones, medicagenin (II) and munchiwarin (III), from Crotalaria medicagenia, which exhibited antimalarial activity against Plasmodium falciparum. A library of 88 chalcones were synthesized and evaluated for their in vitro antimalarial activity. Among these, 67,

  从中国甘草的根中分离得到的Licochalcone A（I）是迄今为止报道的最有前途的抗疟化合物。在继续我们的药物发现计划时，我们从猪屎豆属中分离了两个类似的查耳酮，medicageninin（II）和munchiwarin（III），它们对恶性疟原虫具有抗疟活性。合成了88个查耳酮的文库，并对其体外抗疟活性进行了评估。在这些中，67，68，74，77，和78显示出在体外对抗疟疾活性良好恶性疟原虫具有低细胞毒性的3D7和K1菌株。这些查耳酮还显示出寄生虫约瑟氏疟原虫（N-67株）感染的瑞士小鼠的寄生虫病减少和存活时间增加。药代动力学研究表明，不良的ADME特性导致口服生物利用度低。分子对接研究揭示了这些抑制剂在falcipain-2（FP-2）酶的活性位点的结合方向。化合物67，68，和78显示出对主要血红蛋白降解半胱氨酸适度抑制活性蛋白酶FP-2。
• 프레닐찰콘 및 피라노찰콘 화합물 합성방법
  申请人：Industry Academic Cooperation Foundation, Hallym University 한림대학교 산학협력단(220070195175) BRN ▼221-82-10284

  公开号：KR20170024291A

  公开（公告）日：2017-03-07

  본 발명자들은 클라이젠-슈미트 응축 (Claisen-Schmidt condensation)을 주요 단계로 이용하여 천연 프레닐 찰콘 및 피라노찰콘 화합물 1-9를 합성하는 간단하고 효과적인 방법을 발명하였다. 또한, 합성한 화합물들의 항염증 효과를 지다당으로 자극한 RAW 264.7 대식세포에서 평가하였다. 그 결과, 원환 A (아세토페논 부분)에 프레닐기를 가진 찰콘 화합물은 산화질소 생성에 대해 약한 억제 또는 억제를 나타내지 않은 반면, 원환 A에 프레닐기를 갖지 않은 찰콘 (5, 6, 8 및 9)은 보통 내지는 좋은 활성을 나타내었으며, 세포독성은 없었다.

  The inventors have developed a simple and effective method for synthesizing natural prenyl chalcones and pyranochalcones compounds 1-9 using Claisen-Schmidt condensation as a key step. Furthermore, the anti-inflammatory effects of the synthesized compounds were evaluated on RAW 264.7 macrophage cells stimulated by lipopolysaccharide. As a result, chalcone compounds with prenyl groups on ring A (acetophenone moiety) showed weak inhibition or no inhibition of nitric oxide production, while chalcones without prenyl groups on ring A (5, 6, 8, and 9) exhibited moderate to good activity with no cytotoxicity.
• Synthesis of Isobavachalcone and Some Organometallic Derivatives
  作者：John P. Grealis、Helge Müller-Bunz、Yannick Ortin、Michael Casey、Michael J. McGlinchey

  DOI：10.1002/ejoc.201201063

  日期：2013.1

  with 2 M HCl in methanol to form isobavachalcone in an overall yield of 15 % over five steps. The X-ray crystal structures of 2,4-dihydroxy-3-iodoacetophenone (21) and of several prenylated chalcones are reported, including the elucidation of their hydrogen-bonding networks in the solid state. The synthetic route has been extended to include organometallic derivatives in which the 4-(methoxymethoxy)benzaldehyde

  Isobavachalcone [2',4,4'-trihydroxy-3'-(3"-methyl-2"-butenyl)chalcone, 1] 是一种异戊二烯化查尔酮，具有广泛的生物活性，特别是对抗神经母细胞瘤，神经母细胞瘤是最常见的癌症婴儿期。它目前可以通过从 Psoralea corylifolia 和许多其他非洲和亚洲植物中提取，以 190 美元/mg 的价格在商业上获得。已经探索了几种合成路线，最有效的程序包括钯催化的 3-碘-2,4-双（甲氧基甲氧基）苯乙酮（25）与异戊二烯三丁基锡的 Stille 偶联，Claisen-Schmidt 缩合与 4-（甲氧基甲氧基）苯甲醛形成三重 MOM 保护的异戊二烯查耳酮 27，最后用甲醇中的 2 M HCl 脱保护，以 15% 的总产率在五个步骤中形成异巴伐他酮。2的X射线晶体结构，4-dihydroxy-3-iodoacetophenone
• Regioselectivity in the ene reaction of singlet oxygen with ortho-prenylphenol derivatives
  作者：Jean-Jacques Helesbeux、Olivier Duval、David Guilet、Denis Séraphin、David Rondeau、Pascal Richomme

  DOI：10.1016/s0040-4020(03)00733-6

  日期：2003.6

  The ene reaction of singlet oxygen with prenylated dihydroxyacetophenones led to the 2-hydroperoxy-3-methylbut-3-enyl derivatives as the major product. This original regioselectivity outlined a new effect, in competition with the previously established large group non-bonding effect. The oxidation products distribution could be explained by a stabilising interaction between the phenolic hydrogen, ortho

  单线态氧与烯丙基化的二羟基苯乙酮的烯反应导致以2-氢过氧-3-甲基丁-3-烯基衍生物为主要产物。这种原始的区域选择性概述了一种新的作用，与先前确立的大分子非键合作用相竞争。氧化产物的分布可以通过在异戊二烯基侧链邻位的酚氢与过氧化物中间体之间的稳定相互作用来解释。