(2E)-1-[2,4-二羟基-3-(3-甲基-2-丁烯基)苯基]-3-苯基-2-丙烯-1-酮 | 52601-05-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: (2E)-1-[2,4-二羟基-3-(3-甲基-2-丁烯基)苯基]-3-苯基-2-丙烯-1-酮
• 英文名称: Isocordoin
• 英文别名: 2',4'-dihydroxy-3'-(3-methylbut-2-enyl)chalcone；3'-dimethylallyl-2',4'-dihydroxychalcone；2',4'-dihydroxy-3'-prenylchalcone；Flemistricin-A；Flemistrictin；(E)-1-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-3-phenylprop-2-en-1-one
• CAS: 52601-05-5
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: CHWWSUSAPRACBZ-FMIVXFBMSA-N

物化性质

• 沸点：
  508.4±50.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  (2E)-1-[2,4-二羟基-3-(3-甲基-2-丁烯基)苯基]-3-苯基-2-丙烯-1-酮 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 以94%的产率得到(E)-1-(5-hydroxy-2,2-dimethylchroman-6-yl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  BF3–Et2O mediated biogenetic type synthesis of chromanochalcones from prenylated chalcones via a regioselective cyclization reaction

  摘要：

  In continuation of out-program on synthetic chalcones. we have developed a simple and convenient method for the synthesis of chromanochalcones from prenylated chalcones in high yields by regioselective cyclization using BF3-Et2O. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.124
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 氢氧化钾 、 prenyltransferase 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 288.75h， 生成 (2E)-1-[2,4-二羟基-3-(3-甲基-2-丁烯基)苯基]-3-苯基-2-丙烯-1-酮
  参考文献：
  名称：

  Synthesis and Biosynthesis of Isocordoin

  摘要：

  为了寻找异胭脂虫草素（1）（一种潜在的抗癌天然产物）的简便合成方法，我们将 2′,4′-二羟基查尔酮接种到黑桑树的细胞悬浮培养物中，预计这些培养物中含有活性的前酰基转移酶。24 小时后，目标化合物很容易从代谢物提取物中分离出来。优化生物转化后，炔基衍生物的产率达到 85%。

  DOI：

  10.1055/s-2001-15814

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）。
• Hemi-Synthesis and Anti-Oomycete Activity of Analogues of Isocordoin
  作者：Beatriz Escobar、Iván Montenegro、Joan Villena、Enrique Werner、Patricio Godoy、Yusser Olguín、Alejandro Madrid

  DOI：10.3390/molecules22060968

  日期：——

  An efficient synthesis of a series of 4′-oxyalkyl-isocordoin analogues (2–8) is reported for the first time. Their structures were confirmed by 1H-NMR, 13C-NMR, and HRMS. Their anti-oomycete activity was evaluated by mycelium and spores inhibition assay against two selected pathogenic oomycetes strains: Saprolegnia parasitica and Saprolegnia australis. The entire series of isocordoin derivatives (except compound 7) showed high inhibitory activity against these oomycete strains. Among them, compound 2 exhibited strong activity, with minimum inhibitory concentration (MIC) and minimum oomyceticidal concentration (MOC) values of 50 µg/mL and 75 µg/mL, respectively. The results showed that 4′-oxyalkylated analogues of isocordoin could be potential anti-oomycete agents.

  首次报道了一系列4′-烯基异喹啉类类似物（2-8）的高效合成。通过氢核磁共振（1H-NMR）、碳核磁共振（13C-NMR）和高分辨率质谱（HRMS）确认了它们的结构。通过对两种选定的致病卵菌菌株：腐霉（Saprolegnia parasitica）和南方腐霉（Saprolegnia australis）进行菌丝体和孢子抑制实验，评估了它们的抗卵菌活性。除化合物7外，所有的异喹啉衍生物对这些卵菌菌株均表现出较强的抑制活性。其中，化合物2展现出强效活性，最小抑菌浓度（MIC）和最小卵菌杀伤浓度（MOC）值分别为50 µg/mL和75 µg/mL。结果表明，4′-烯基化的异喹啉类类似物可能成为潜在的抗卵菌药物。
• Molecular Characterization and Phylogenetic Analysis of Two Novel Regio-specific Flavonoid Prenyltransferases from Morus alba and Cudrania tricuspidata
  作者：Ruishan Wang、Ridao Chen、Jianhua Li、Xiao Liu、Kebo Xie、Dawei Chen、Yunze Yin、Xiaoyu Tao、Dan Xie、Jianhua Zou、Lin Yang、Jungui Dai

  DOI：10.1074/jbc.m114.608265

  日期：2014.12

  distributed in several plant families. The prenylation catalyzed by prenyltransferases represents a Friedel-Crafts alkylation of the flavonoid skeleton in the biosynthesis of natural prenylated flavonoids and contributes to the structural diversity and biological activities of these compounds. To date, all identified plant flavonoid prenyltransferases (FPTs) have been identified in Leguminosae. In the

  异戊二烯化黄酮是有吸引力的特殊代谢物，具有广泛的生物活性，分布在几个植物科中。异戊二烯基转移酶催化的异戊二烯化代表了天然异戊二烯化黄酮类化合物生物合成中类黄酮骨架的 Friedel-Crafts 烷基化，有助于这些化合物的结构多样性和生物活性。迄今为止，所有已鉴定的植物类黄酮异戊二烯基转移酶 (FPT) 都已在豆科植物中得到鉴定。在本研究中，分别从桑科植物 M. alba 和 C. tricuspidata 中鉴定了两种新的 FPT，即桑树异甘草素 3'-二甲基烯丙基转移酶 (MaIDT) 和柘木异甘草素 3'-二甲基烯丙基转移酶 (CtIDT)。MaIDT 和 CtIDT 与豆科 FPT 具有低水平的同源性。MaIDT 和 CtIDT 被预测为膜结合蛋白，具有预测的转运肽、七个跨膜区域和与其他异戊二烯酸转移酶相似的保守功能域。重组 MaIDT 和 CtIDT 能够区域选择性地将二甲基烯丙
• PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
  申请人：McMaster University

  公开号：US20210380513A1

  公开（公告）日：2021-12-09

  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).
• Synthesis and Biosynthesis of Isocordoin
  作者：Alberto Vitali、Franco Ferrari、Giuliano Delle Monache、Ezio Bombardelli、Bruno Botta

  DOI：10.1055/s-2001-15814

  日期：——

  In the search of a convenient synthesis for isocordoin (1), a potential anticancer natural product, 2′,4′-dihydroxychalcone was inoculated in cell suspension cultures of Morus nigra, which were expected to contain an active prenyltransferase. After 24 hours the target compound was easily isolated from the metabolite extract. Optimization of the biotransformation resulted in a 85 % yield of the prenyl derivative.

  为了寻找异胭脂虫草素（1）（一种潜在的抗癌天然产物）的简便合成方法，我们将 2′,4′-二羟基查尔酮接种到黑桑树的细胞悬浮培养物中，预计这些培养物中含有活性的前酰基转移酶。24 小时后，目标化合物很容易从代谢物提取物中分离出来。优化生物转化后，炔基衍生物的产率达到 85%。