2-(4-hydroxybenzyl)-6-methoxybenzofuran-3(2H)-one | 77412-34-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: 2-(4-hydroxybenzyl)-6-methoxybenzofuran-3(2H)-one
• 英文别名: 2-(4-hydroxybenzyl)-6-methoxybenzofuran-3(2H)-one
• CAS: 77412-34-1
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: SAICHUNXPSFZDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (Z)-2-(4-hydroxybenzylidene)-6-methoxybenzofuran-3(2H)-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 以82%的产率得到2-(4-hydroxybenzyl)-6-methoxybenzofuran-3(2H)-one
  参考文献：
  名称：

  Design, Synthesis and Biological Activities of Dihydroaurones

  摘要：

  为了扩大奥罗宁在无色食品和化妆品应用中的适用性，设计了一系列二氢奥罗宁，以模拟天然奥罗宁和合成奥罗宁。通过氢化反应从相应的奥罗宁合成了这些二氢奥罗宁。对这些二氢奥罗宁及其对应的奥罗宁进行了抗氧化、抗炎和酪氨酸酶抑制活性的筛选。合成的二氢奥罗宁（3b-f）在超氧自由基清除实验中表现出比标准的没食子酸更优越的抗氧化活性。二氢奥罗宁（3b-f）还表现出显著的酪氨酸酶抑制活性，其中两种二氢奥罗宁（3h、3j）显示出有希望的5-脂氧酶抑制活性。

  DOI：

  10.14233/ajchem.2021.23139

文献信息

• A novel α-hydroxydihydrochalcone from the heartwood of Pterocarpus angolensis D.C.: absolute configuration, synthesis, photochemical transformations, and conversion into α-methyldeoxybenzoins
  作者：Barend C. B. Bezuidenhoudt、E. Vincent Brandt、David G. Roux

  DOI：10.1039/p19810000263

  日期：——

  The absolute configuration of (αR)-α,2′-dihydroxy-4,4′-dimethoxydihydrochalcone from the heartwood of Pterocarpus angolensis D.C. is established. Its structure is substantiated by synthesis and by photochemical conversion of its α-O-tosyl derivative into an α-tosyloxymethyldeoxybenzoin and hence to the α-methyldeoxybenzoin analogue. The photochemical step also leads, amongst others, to α-hydroxymethyldeoxybenzoin

  （α的绝对构型[R）-α，2'-二羟基-4,4'- dimethoxydihydrochalcone从心材紫檀angolensis DC成立。通过合成以及通过将其α- O-甲苯磺酰基衍生物光化学转化为α-甲苯磺酰氧基甲基脱氧安息香素并因此转化为α-甲基脱氧安息香类似物来证实其结构。根据光解的条件，光化学步骤还导致α-羟甲基脱氧安息香素，β-羟基二氢查耳酮和2-苄基苯并呋喃-3-酮类似物。
• Design, Synthesis and Biological Activities of Dihydroaurones
  作者：Somepalli Venkateswarlu、Gandrotu Narasimha Murty、Meka Satyanarayana、Vidavalur Siddaiah

  DOI：10.14233/ajchem.2021.23139

  日期：——

  To widen aurones applicability in achromatic food and cosmetic applications, a series of dihydroaurones were designed to mimic natural aurones as well as synthetic aurones. Dihydroaurones have been synthesized from the corresponding aurones by hydrogenation. These dihydroaurones and their corresponding aurones were screened for antioxidant, anti-inflammatory and tyrosinase enzyme inhibitory activity. Synthesized dihydroaurones (3b-f) displayed superior antioxidant activity in superoxide free radical scavenging assay than the standard gallic acid. Dihydroaurones (3b-f) also exhibited significant tyrosinase enzyme inhibitory activity and two dihydroaurones (3h, 3j) showed promising 5-lipoxygenase inhibitory activity.

  为了扩大奥罗宁在无色食品和化妆品应用中的适用性，设计了一系列二氢奥罗宁，以模拟天然奥罗宁和合成奥罗宁。通过氢化反应从相应的奥罗宁合成了这些二氢奥罗宁。对这些二氢奥罗宁及其对应的奥罗宁进行了抗氧化、抗炎和酪氨酸酶抑制活性的筛选。合成的二氢奥罗宁（3b-f）在超氧自由基清除实验中表现出比标准的没食子酸更优越的抗氧化活性。二氢奥罗宁（3b-f）还表现出显著的酪氨酸酶抑制活性，其中两种二氢奥罗宁（3h、3j）显示出有希望的5-脂氧酶抑制活性。