diapocynin | 29799-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diapocynin
• 英文别名: dehydrodiacetovanillone；1,1'-(6,6'-dihydroxy-5,5'-dimethoxy-1,1'-biphenyl-3,3'-diyl)diethanone；1,1'-(6,6'-dihydroxy-5,5'-dimethoxy-(1,1'-biphenyl)-3,3'-diyl)-bis-(ethan-1-one)；1-[3-(5-acetyl-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxyphenyl]ethanone
• CAS: 29799-22-2
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: HLNDPICGHQGWSU-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMSO：可溶，2mg/mL，澄清（加热）

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  diapocynin 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以88%的产率得到dehydrodiapocynol
  参考文献：
  名称：

  Regioselectivity in oxidative cross-coupling of phenols. Application to the synthesis of dimeric neolignans

  摘要：

  The problems of regioselectivity in oxidative coupling of phenols are outlined, and recent research on the application to the synthesis of lignans and neolignans is reviewed. Lignans and neolignans are dimers that are typically formed by oxidative coupling of propenyl phenols. The coupling of structurally different phenols (cross-coupling) is an extension of this synthesis. Recent results show that cross-coupling can be achieved if the phenols have compatible reactivities. The regioselectivity is often quite different in cross-coupling compared to dimerization. Coupling of phenols with widely different rates of oxidation is difficult but can be achieved if the concentration of the more reactive phenol can be kept low enough during the reaction, for instance by diffusion through a dialysis membrane. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00943-1
• 作为产物：
  描述：

  香草乙酮 在 ferrous(II) sulfate heptahydrate 、 sodium persulfate 作用下， 以 水 为溶剂， 反应 0.08h， 生成 diapocynin
  参考文献：
  名称：

  香兰素和Apocynin的同调通过抑制FAK / PI3K / Akt信号通路降低人癌细胞的转移潜能

  摘要：

  在称为转移的过程中，癌细胞向远处器官的扩散是导致癌症患者大多数死亡的主要因素。香草调味剂香草醛已经显示出可以抑制小鼠模型中的转移。在这里，我们评估了食品添加剂香兰素的同型二聚体二香兰素及其在肝细胞癌细胞中与结构相关的化合物载脂蛋白和双apocynin的抗转移潜力。Transwell侵袭试验表明，二聚体形式在抑制侵袭方面比香草醛和载脂蛋白具有更高的效力，二聚体的IC 50值为23.3±7.4至41.3±4.2μM，比IC低26-34倍香兰素和载脂蛋白的50值（p<0.05）。单体和二聚体形式均通过抑制FAK和Akt的磷酸化来靶向控制侵袭过程。分子对接研究表明，二聚体与FAK FERM结构域的Y397口袋的结合应比香草醛和载脂蛋白更紧密。因此，食品添加剂香兰素具有比调味剂香兰素更大的抗转移潜力。

  DOI：

  10.1021/acs.jafc.6b05697

文献信息

• An efficient and flexible synthesis of model lignin oligomers
  作者：W. Graham Forsythe、Mark D. Garrett、Christopher Hardacre、Mark Nieuwenhuyzen、Gary N. Sheldrake

  DOI：10.1039/c3gc41110a

  日期：——

  The use of model compounds in the development of selective lignin depolymerisation processes has been limited by the lack of complexity of these models compared with lignin itself. In this paper we report a convergent and efficient synthetic method for the flexible, multi-gram preparation of model lignin hexamers and octamers containing three of the most common connectivity motifs found within native lignin, namely β-O-4′, 5-5′ and β-5′, which will be used to further the mechanistic understanding of lignin depolymerisation processes.

  在发展选择性木质素解聚过程方面，模型化合物应用受限，因其复杂性不足，与木质素本身相去甚远。本文中，我们报道了合成模型木质素六聚体和八聚体的集约而高效的方法，可灵活制备多克量产品。模型化合物包含三种最常见的连接模式，即β-O-4′、5-5′和β-5′，这些模式存在于天然木质素中。我们将运用这些模型化合物，进一步深化对木质素解聚过程机理的理解。
• Stereoselective oxazaborolidine–borane reduction of biphenyl alkyl diketones–lignin models: enantiopure dehydrodiapocynol derivatives
  作者：Giovanna Delogu、Maria Antonietta Dettori、Angela Patti、Sonia Pedotti、Alessandra Forni、Gianluigi Casalone

  DOI：10.1016/s0957-4166(03)00449-x

  日期：2003.8

  Asymmetric reduction of two conformationally flexible biphenyl alkyl diketones 9 and 10 with (R)-oxazaborolidine 3-borane system was successfully carried out and the corresponding biphenyl alcohols 11 and 12 were obtained in high yield and e.e. with predominance of the homochiral (S,S) dicarbinols. The absolute configuration of diastereopure dehydrodiapocynol derivative (S,S)-14 was assigned by crystallographic

  2个构象柔性联苯烷基二酮的不对称还原9和10与（[R）-oxazaborolidine 3 -硼烷系统成功地进行了与相应的联苯醇11和12以高收率和EE获得与纯手性的优势（小号，小号）双卡宾醇。通过晶体学分析确定了非对映体脱氢二嘧啶醇衍生物（S，S）-14的绝对构型，这证实了CBS催化的酮还原的已知立体化学过程，并提供了有关空间排列的有用信息。
• Process for preparing biphenyl compounds
  申请人：UNIVERSITÉ DE BORDEAUX

  公开号：US10155969B2

  公开（公告）日：2018-12-18

  The present invention relates to a process for preparing a compound having the formula (I), said process comprising the following steps: a) the addition of an oxygen source into a solution of a compound of formula (II), in a water-miscible solvent, b) the addition of a laccase in the solution obtained after step a); and c) the possible recovering of the compound of formula (I) thus obtained.

  本发明涉及一种制备具有化学式(I)的化合物的方法，该方法包括以下步骤：a)将氧源加入到具有化学式(II)的化合物的溶液中，溶剂为水溶性溶剂；b)将漆酶加入到步骤a)得到的溶液中；c)可能回收所得到的具有化学式(I)的化合物。
• [EN] NEUROPROTECTIVE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS NEUROPROTECTEURS ET LEUR UTILISATION
  申请人：MCW RES FOUND INC

  公开号：WO2010126719A1

  公开（公告）日：2010-11-04

  Apocynin derivative compounds, active pharmaceutical ingredients, dosage forms, and methods of use thereof as neuroprotectants in the brain of mammals.

  阿波西宁衍生物化合物，作为哺乳动物大脑中的神经保护剂的活性药用成分，剂型和使用方法。
• Experimental, DFT and docking simulations of the binding of diapocynin to human serum albumin: induced circular dichroism
  作者：Diego Venturini、Bruna Pastrello、Maria Luiza Zeraik、Ivani Pauli、Adriano Defini Andricopulo、Luiz Carlos Silva-Filho、V. S. Bolzani、Nelson Henrique Morgon、A. R. da Souza、Valdecir Farias Ximenes

  DOI：10.1039/c5ra10960d

  日期：——

  Axial chirality in diapocynin induced by human albumin.

  人类白蛋白诱导二氢紫草酸的轴向手性。