4,4'-(6,6'-dihydroxy-5,5'-dimethoxy-[1,1'-biphenyl]-3,3'-diyl)bis(butan-2-one) | 1112137-79-7

• 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: 4,4'-(6,6'-dihydroxy-5,5'-dimethoxy-[1,1'-biphenyl]-3,3'-diyl)bis(butan-2-one)
• 英文别名: 4-[4-Hydroxy-3-[2-hydroxy-3-methoxy-5-(3-oxobutyl)phenyl]-5-methoxyphenyl]butan-2-one；4-[4-hydroxy-3-[2-hydroxy-3-methoxy-5-(3-oxobutyl)phenyl]-5-methoxyphenyl]butan-2-one
• CAS: 1112137-79-7
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: YDPYZCOLINNKNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-(6,6'-dihydroxy-5,5'-dimethoxy-[1,1'-biphenyl]-3,3'-diyl)bis(butan-2-one) 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  类姜油醇衍生物和相关联苯的立体选择性酯交换反应中的脂肪酶行为

  摘要：

  使用基于在有机溶剂中的醇功能的不可逆酯交换反应的高度立体选择性酶促程序，获得了高光学纯度的姜油醇和脱氢油姜油醇O-甲基衍生物1和2的对映异构体。然后将生物催化方法扩展到相应的联苯衍生物5-8，对其在整个外消旋/内消旋混合物上进行一锅拆分/脱对称，得到对映异构体和非对映异构体过量非常高的单一立体异构体。荧光假单胞菌脂肪酶AK在单体（±）-1酯交换反应中的动力学和对映选择性行为的比较并制备了相关的（±）-5和meso- 6联苯二聚体。

  DOI：

  10.1016/j.molcatb.2013.01.007
• 作为产物：
  描述：

  姜酮 在 Colletotrichum gloeosporioides 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 360.0h， 生成 4,4'-(6,6'-dihydroxy-5,5'-dimethoxy-[1,1'-biphenyl]-3,3'-diyl)bis(butan-2-one)
  参考文献：
  名称：

  Colletotrichum gloeosporioides 对生姜 (Zingiber officinale Roscoe) 中刺激性成分的生物转化产生氧化性邻位偶联产物

  摘要：

  摘要 这项工作研究了病原真菌胶孢炭疽菌对生姜成分（姜油酮、[6]-姜烯酚、[6]-姜酚和甲基-[6]-姜酚）的生物转化。. 在有和没有氘标记的化合物的情况下进行实验。产物代谢物通过液相色谱-串联质谱联用和液相色谱固相萃取-核磁共振进行分析。提供给真菌的底物主要通过氧化反应（包括芳香族碳-碳偶联）进入代谢途径。姜油酮和[6]-姜酚生物转化产物包括双酚二聚体。基于中间体 4-(2-羟乙基)-2-甲氧基苯酚的存在，提出了一种用于形成双酚的生物降解途径，通常从 [6]-姜酚和 [6]-姜烯酚生物降解中鉴定出来。该中间体可能源自拜尔-维利格反应，然后是水解。分子的 C-C 偶联可导致酚类氧化邻 - 邻偶联，表明双酚二聚体是C. gloeosporioides漆酶催化的产物。

  DOI：

  10.1080/10242422.2021.1878159

文献信息

• Linkage and Stereochemistry Characters of Phenolic Antioxidant Product Formation
  作者：Xican Li、Xiaojian Ouyang、Ban Chen、Shuqin Liu、Jingyuan Zeng

  DOI：10.1021/acs.jafc.2c06563

  日期：——

  antioxidant product is formed via linear linkage or furanocyclic linkage. The linear linkage is fulfilled via a radical coupling and controlled by the O–O linkage exclusion, meta-linkage exclusion, and catechol-activated principles. However, when an exocyclic π-bond conjugates with the phenolic core and is affixed at the −OH para-position, the furanocyclic linkage may occur via a subsequent intramolecular

  本研究开发了一种巧妙而新颖的策略来阐明酚类抗氧化剂产品形成过程中的连接和立体化学特征。一系列酚类异构体或类似物用 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide 自由基处理，在水溶液中产生 16 个抗氧化剂二聚反应。通过超高效液相色谱结合电喷雾电离四极杆飞行时间串联质谱法快速鉴定产物。通过对这些反应进行系统的功能-结构关系分析和理论计算，得出结论，酚类抗氧化剂产物通过线性键或呋喃环键形成。线性连接通过自由基耦合实现，并由 O-O 连接排斥控制，元连锁排除和儿茶酚激活原理。然而，当环外 π 键与酚核共轭并固定在 -OH 对位时，呋喃环连接可能通过随后的分子内迈克尔加成发生。分子内加成总是缺乏 Re-attack 以显示“α,β 非对映选择性”。α,β 非对映选择性是酚类抗氧化产物形成过程中呋喃环键的立体化学特征。所有这些新发现不仅
• Synthesis of new ferrocenyl dehydrozingerone derivatives and their effects on viability of PC12 cells
  作者：Sonia Pedotti、Angela Patti、Sonia Dedola、Antonio Barberis、Davide Fabbri、Maria Antonietta Dettori、Pier Andrea Serra、Giovanna Delogu

  DOI：10.1016/j.poly.2016.05.039

  日期：2016.10

  A series of novel compounds deriving from the conjugation of ferrocene with curcumin-related bioactive molecules as dehydrozingerone, zingerone and their biphenyl dimers was prepared by Claisen-Schmidt condensation of the suitable aromatic aldehydes and acetylferrocene in different conditions according to the starting material. The obtained compounds were fully characterized by NMR spectroscopy and cyclic voltammetry and reversible electrochemical behavior was recorded for monomer derivatives. The cell viability of PC12 cells after exposure to the organometallic compounds was also evaluated and a reduced toxicity with respect to the ferrocene was detected. In comparison with biphenyl 4, a compound that manifested antiproliferative and apoptotic activities and was quite toxic on PC12 cells, the exposure to the ferrocenyl analogue 14 resulted in roughly fourfold increase in the cell viability. Ferrocenyl chalcones 14 and 16-18 significantly increased the oxidative stress generated by hydrogen peroxide, a molecule generally accumulated in cancer cells and, recently, studied as prodrug. (C) 2016 Elsevier Ltd. All rights reserved.
• Small molecules interacting with α-synuclein: antiaggregating and cytoprotective properties
  作者：Anna Marchiani、Stefano Mammi、Giuliano Siligardi、Rohanah Hussain、Isabella Tessari、Luigi Bubacco、Giovanna Delogu、Davide Fabbri、Maria A. Dettori、Daniele Sanna、Sonia Dedola、Pier A. Serra、Paolo Ruzza

  DOI：10.1007/s00726-013-1503-3

  日期：2013.8

  Curcumin, a dietary polyphenol, has shown a potential to act on the symptoms of neurodegenerative disorders, including Alzheimer's and Parkinson's diseases, as a consequence of its antioxidant, anti-inflammatory and anti-protein aggregation properties. Unfortunately, curcumin undergoes rapid degradation at physiological pH into ferulic acid, vanillin and dehydrozingerone, making it an unlikely drug candidate. Here, we evaluated the ability of some curcumin by-products: dehydrozingerone (1), its O-methyl derivative (2), zingerone (3), and their biphenyl analogues (4-6) to interact with alpha-synuclein (AS), using CD and fluorescence spectroscopy. In addition, the antioxidant properties and the cytoprotective effects in rat pheochromocytoma (PC12) cells prior to intoxication with H2O2, MPP+ and MnCl2 were examined while the Congo red assay was used to evaluate the ability of these compounds to prevent aggregation of AS. We found that the biphenyl zingerone analogue (6) interacts with high affinity with AS and also displays the best antioxidant properties while the biphenyl analogues of dehydrozingerone (4) and of O-methyl-dehydrozingerone (5) are able to partially inhibit the aggregation process of AS, suggesting the potential role of a hydroxylated biphenyl scaffold in the design of AS aggregation inhibitors.
• Sustainable Electropolymerization of Zingerone and Its C2 Symmetric Dimer for Amperometric Biosensor Films
  作者：Myriam Caval、Maria Antonietta Dettori、Paola Carta、Roberto Dallocchio、Alessandro Dessì、Salvatore Marceddu、Pier Andrea Serra、Davide Fabbri、Gaia Rocchitta

  DOI：10.3390/molecules28166017

  日期：——

  Polymeric permselective films are frequently used for amperometric biosensors to prevent electroactive interference present in the target matrix. Phenylenediamines are the most commonly used for the deposition of shielding polymeric films against interfering species; however, even phenolic monomers have been utilized in the creation of these films for microsensors and biosensors. The purpose of this paper is to evaluate the performances of electrosynthesized polymers, layered by means of constant potential amperometry (CPA), of naturally occurring compound zingerone (ZING) and its dimer dehydrozingerone (ZING DIM), which was obtained by straight oxidative coupling reaction. The polymers showed interesting shielding characteristics against the main interfering species, such as ascorbic acid (AA): actually, polyZING exhibited an AA shielding aptitude comprised between 77.6 and 99.6%, comparable to that obtained with PPD. Moreover, a marked capability of increased monitoring of hydrogen peroxide (HP), when data were compared with bare metal results, was observed. In particular, polyZING showed increases ranging between 55.6 and 85.6%. In the present work, the molecular structures of the obtained polymers have been theorized and docking analyses were performed to understand their peculiar characteristics better. The structures were docked using the Lamarckian genetic algorithm (LGA). Glutamate biosensors based on those polymers were built, and their performances were compared with biosensors based on PPD, which is the most widespread polymer for the construction of amperometric biosensors.
• Lipase behavior in the stereoselective transesterification of zingerol-like derivatives and related biphenyls
  作者：Claudia Sanfilippo、Angela Patti、Maria Antonietta Dettori、Davide Fabbri、Giovanna Delogu

  DOI：10.1016/j.molcatb.2013.01.007

  日期：2013.6

  irreversible transesterification of alcoholic functions in organic solvent, both enantiomers of zingerol and dehydrozingerol O-methyl derivatives 1 and 2 were obtained in high optical purity. The biocatalytic method was then extended to the corresponding biphenyl derivatives 5–8 for which an one-pot resolution/desymmetrization was carried out on the whole racemic/meso mixtures to give single stereoisomers

  使用基于在有机溶剂中的醇功能的不可逆酯交换反应的高度立体选择性酶促程序，获得了高光学纯度的姜油醇和脱氢油姜油醇O-甲基衍生物1和2的对映异构体。然后将生物催化方法扩展到相应的联苯衍生物5-8，对其在整个外消旋/内消旋混合物上进行一锅拆分/脱对称，得到对映异构体和非对映异构体过量非常高的单一立体异构体。荧光假单胞菌脂肪酶AK在单体（±）-1酯交换反应中的动力学和对映选择性行为的比较并制备了相关的（±）-5和meso- 6联苯二聚体。