4,5,4',5'-bis(methylenedioxy)biphenyl-2,2'-diol | 69276-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4,5,4',5'-bis(methylenedioxy)biphenyl-2,2'-diol
• 英文别名: (5,5'-Bibenzo(D)(1,3)dioxole)-6,6'-diol；6-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-benzodioxol-5-ol
• CAS: 69276-88-6
• 化学式: C₁₄H₁₀O₆
• 分子量: 274.23
• InChiKey: LNOXWGDBXZCNET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5,4',5'-bis(methylenedioxy)biphenyl-2,2'-diol 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 四氯化碳 、 水 为溶剂， 生成 4,5,4',5'-Bismethylendioxydipheno-2,2'-chinon
  参考文献：
  名称：

  Hewgill, Frank R.; Greca, Bart La; Legge, Frank, Journal of the Chemical Society. Perkin transactions I, 1983, # 1, p. 131 - 134

  摘要：

  DOI：
• 作为产物：
  描述：

  芝麻酚 在 dioxide titanium 作用下， 以69 %的产率得到4,5,4',5'-bis(methylenedioxy)biphenyl-2,2'-diol
  参考文献：
  名称：

  可见光诱导酚和烯基酚与可回收固体光催化剂的氧化偶联

  摘要：

  据报道，使用廉价的异质二氧化钛光催化剂在空气和可见光下进行苯酚和烯基苯酚氧化偶联的光催化方法。在偶联过程中，钛-基质络合物在可见光下通过配体到金属的电荷转移效应被激活，并通过自由基阳离子形成联苯酚加合物。非均相TiO 2催化剂在整个反应过程中保持稳定，并且可以轻松去除并重复使用多次。

  DOI：

  10.1021/acs.orglett.2c04122

文献信息

• Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols
  作者：Nagnath Yadav More、Masilamani Jeganmohan

  DOI：10.1039/c7cc04829g

  日期：——

  A regioselective synthesis of unsymmetrical and symmetrical biphenols and binaphthols via oxidative coupling of phenols or naphthols in the presence of K2S2O8 in CF3COOH at ambient conditions is described. Interestingly, 1:1 ratio of H2O and CH3CN solvent mixtures at 80 °C instead of CF3COOH provided substituted unsymmetrical quinones. A gram scale synthesis of biphenols and binaphthols was demonstrated

  描述了在环境条件下在CF 3 COOH中在K 2 S 2 O 8存在下通过酚或萘酚的氧化偶联的不对称和对称的双酚和联萘酚的区域选择性合成。有趣的是，在80°C的H2O和CH3CN溶剂混合物以1：1的比例代替CF3COOH提供了取代的不对称醌。证明了双酚和联萘酚的克级合成。
• <i>ortho</i>-Selective Phenol-Coupling Reaction by Anodic Treatment on Boron-Doped Diamond Electrode Using Fluorinated Alcohols
  作者：Axel Kirste、Martin Nieger、Itamar M. Malkowsky、Florian Stecker、Andreas Fischer、Siegfried R. Waldvogel

  DOI：10.1002/chem.200802556

  日期：2009.2.23

  Enlarged scope by fluorinated mediators: Oxyl radicals are easily formed on boron‐doped diamond (BDD) electrodes and can be exploited for the ortho‐selective coupling to the corresponding biphenols (see scheme). At partial conversion, a clean transformation is achieved that can be applied to electron‐rich as well as fluorinated phenols.

  氟化介质扩大了范围：氧自由基很容易在掺硼金刚石（BDD）电极上形成，可用于与相应双酚的邻位选择性偶联（参见方案）。在部分转化时，可以实现干净的转化，该转化可以应用于富电子以及氟化酚。
• Novel Template-Directed Anodic Phenol-Coupling Reaction
  作者：Itamar M. Malkowsky、Christina E. Rommel、Roland Fröhlich、Ulrich Griesbach、Hermann Pütter、Siegfried R. Waldvogel

  DOI：10.1002/chem.200600375

  日期：2006.9.25

  Substituted phenols were anodically coupled to the corresponding 2,2'-biphenols via tetraphenoxy borate derivatives. This electrochemical method is particularly useful for methyl-substituted substrates, such as 2,4-dimethyl phenol. The selective ortho-coupling reaction can be easily performed on a multikilogram scale.

  通过四苯氧基硼酸酯衍生物将取代的酚与相应的2,2'-双酚进行阳极偶联。该电化学方法对于甲基取代的底物，例如2，4-二甲基苯酚特别有用。选择性邻位偶联反应可以轻松地在几千克规模上进行。
• Studies on the antioxidants. XIV. Reaction of sesamol with hydrogen peroxide-peroxidase.
  作者：TSUTAO KURECHI、KIYOMI KIKUGAWA、SHUJI AOSHIMA

  DOI：10.1248/cpb.29.2351

  日期：——

  Sesamol (I) was transformed into a fluorescent product (II) and a violet-colored product (IV) by mild oxidation with hydrogen peroxide catalyzed by horseradish peroxidase. The product (II) was elucidated to be 2, 2'-dihydroxy-4, 5 ; 4', 5'-bis (methylenedioxy) biphenyl and the structure of IV was assumed to be the highly conjugated quinoid form of II. The product (II) was transformed into IV by hydrogen peroxide-peroxidase treatment and was regenerated from IV by treatment with reductants. Systems containing II, hydrogen peroxide and peroxidase may provide a new, versatile chromogenic determination method for hydrogen peroxide or peroxidase. Determination of hydrogen peroxide at around 10 μM and peroxidase at around 0.1 nM was possible. Oxidations of I by other means were performed and the results were compared with those obtained with hydrogen peroxide-peroxidase.

  在辣根过氧化物酶的催化下，芝麻酚（I）在过氧化氢的温和氧化作用下转化为荧光产物（II）和紫罗兰色产物（IV）。产物（II）被确定为 2，2'-二羟基-4，5；4'，5'-双（亚甲基二氧基）联苯，而 IV 的结构被认为是 II 的高度共轭醌形式。通过过氧化氢-过氧化物酶处理，产物（II）转化为 IV，并通过还原剂处理从 IV 中再生。含有 II、过氧化氢和过氧化物酶的体系可以为过氧化氢或过氧化物酶提供一种新的、多功能的色原测定方法。可以测定 10 μM 左右的过氧化氢和 0.1 nM 左右的过氧化物酶。通过其他方法对 I 进行了氧化，并将结果与过氧化氢-过氧化物酶的结果进行了比较。
• An unprecedented oxidative trimerization of sesamol catalyzed by laccases
  作者：Mihaela-Anca Constantin、Jürgen Conrad、Uwe Beifuss

  DOI：10.1016/j.tetlet.2012.04.056

  日期：2012.6

  The laccase-catalyzed oxidative coupling of sesamol, a naturally occurring phenolic antioxidant, with O2 as the oxidant proceeds with high selectivity and delivers a previously unknown trimer in 61% yield. Further experiments demonstrate that the outcome of the sesamol oxidation strongly depends on the catalyst and the oxidant employed.

  天然存在的酚类抗氧化剂芝麻酚的漆酶催化氧化偶合与O 2作为氧化剂，具有高选择性，并以61％的产率提供了以前未知的三聚体。进一步的实验表明，芝麻酚的氧化结果在很大程度上取决于所使用的催化剂和氧化剂。