6,6'-亚甲基二-1,3-苯并二氧戊环-5-醇 | 78188-48-4

• 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
• 中文名称: 6,6'-亚甲基二-1,3-苯并二氧戊环-5-醇
• 英文名称: 6,6′-methylenebis-1,3-benzodioxol-5-ol
• 英文别名: 6,6’-methylenebis(benzo[d][1,3]dioxol-5-ol)；6,6'-Methylenebis-1,3-benzodioxol-5-ol；6-[(6-hydroxy-1,3-benzodioxol-5-yl)methyl]-1,3-benzodioxol-5-ol
• CAS: 78188-48-4
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: PMMQCXVUBOIIPG-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176 °C(Solv: methanol (67-56-1))
• 沸点：
  516.2±50.0 °C(Predicted)
• 密度：
  1.532±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基甲酰胺

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基-N-(2-氯-6-甲基苯基)-5-噻唑酰胺 生成 6,6'-亚甲基二-1,3-苯并二氧戊环-5-醇
  参考文献：
  名称：

  DALLACKER, FRANZ;HOLSCHBACH, MARKUS;HOLSCHBACH, UTE;KONINGS, A. W. T., CHEM.-ZTG., 114,(1990) N-8, C. 225-228

  摘要：

  DOI：

文献信息

• Synthesis and Antioxidant Capacity of Some Derivatives of Sesamol at the C‐6 Position
  作者：Evgeny V. Buravlev、Oksana G. Shevchenko、Kyrill Yu. Suponitsky

  DOI：10.1002/cbdv.202100221

  日期：2021.6

  Several synthetic approaches (aminomethylation, alkylation, condensation, etc.) have been used to synthesize derivatives based on the sesamol (1), natural phenol. The set of methods, including the study of antioxidant activity (AOA) by the ability to inhibit the initiated oxidation of animal lipids, radical scavenging activity, Fe2+-chelation ability, as well as a comparative assessment of membrane-protective

  几种合成方法（氨基甲基化、烷基化、缩合等）已被用于合成基于芝麻酚( 1 )、天然苯酚的衍生物。一套方法，包括通过抑制动物脂质起始氧化的能力、自由基清除活性、Fe 2+ -螯合能力以及膜保护活性的比较评估来研究抗氧化活性 (AOA) H 2 O 2 的条件诱导小鼠红细胞（RBC）溶血，用于分析合成化合物的抗氧化潜力。合成的衍生物在列出的测试系统中表现出不同的活性，我们已经确定了最有希望对其药理特性进行详细研究的化合物。
• Preparation of 2,2'-Dihydroxytriphenylmethanes Using Metal Phenolates with Aromatic Aldehydes.
  作者：Nobuko MIBU、Kunihiro SUMOTO

  DOI：10.1248/cpb.48.1810

  日期：——

  The reactions of oxophilic metal phenolates having electron-donating substituents (1a-c) with aromatic aldehydes (2, 3) were selectively condensed at the ortho-position of the starting phenol to afford 2,2'-dihydroxytriphenylmethanes (8-11). This method was also applicable to the preparation of bisphenols (12-17) starting with naphthaldehydes (4, 5) and pyridinecarboxaldehydes (6, 7), but in low yields

  具有给电子取代基（1a-c）的亲金属性金属酚盐与芳族醛（2，3）的反应在起始酚的邻位选择性缩合，得到2,2'-二羟基三苯基甲烷（8-11）。该方法也适用于以萘醛（4、5）和吡啶甲醛（6、7）为起始原料的双酚（12-17）的制备，但收率低。在这些醛（4-7）的情况下，通过超声处理可以获得令人满意的产率。
• Monoterpene derivatives of sesamol. Synthesis and evaluation of antioxidant properties
  作者：I. Yu. Chukicheva、I. V. Fedorova、O. G. Shevchenko、A. V. Kutchin

  DOI：10.1007/s11172-023-4018-4

  日期：2023.9

  found to be the main direction of the reaction under the conditions studied. For alkyl sesamol derivatives, the erythrotoxicity, membrane-protective and antioxidant activities were evaluated in in vitro models. It was established that 6-isobornylbenzo[d][1,3]dioxol-5-ol is distinguished by a high antioxidant activity in biologically relevant test systems and is significantly superior to sesamol in both

  研究了在酸多相催化剂（KSF、Fiban K-1、Amberlyst 15）存在下芝麻酚与莰烯的烷基化反应。发现O-烷基化是在所研究的条件下反应的主要方向。对于烷基芝麻酚衍生物，在体外模型中评估了红细胞毒性、膜保护和抗氧化活性。经证实，6-异冰片苯并[ d ][1,3]二氧杂环戊醇-5-醇在生物相关测试系统中具有高抗氧化活性，并且在抑制 Fe 2+ /抗坏血酸的能力方面显着优于芝麻酚。 -诱导脑脂质氧化和氧化溶血条件下红细胞的保护。
• Identification of sesamol byproducts produced by plasma treatment with inhibition of advanced glycation endproducts formation and ONOO− scavenging activities
  作者：Yun Hee Jeong、Gyeong Han Jeong、Yong-Ha Jeong、Tae Hoon Kim

  DOI：10.1016/j.foodchem.2020.126196

  日期：2020.6

  Little is known of plasma-mediated relations between major food components and their biological capacities. In the present work, the effects of dielectric barrier discharge (DBD) plasma irradiation on pure sesamol and sesame oil were investigated using spectroscopic (LC-MS, NMR) and bioassay methods. Sesamol was degraded when subjected to plasma irradiation for 40 min, and the exposed products exhibited improved anti-glycation capacities against advanced glycation end products (AGEs) formation and better ONOO- scavenging ability. Structures of newly formed compounds were determined spectroscopically. Quantitative LC-MS analysis of the major products generated in sesamol and sesame oil was achieved using isolates 1-4 of purified sesamol plasma treated for 40 min. These results indicate that the predominant chemical changes induced in sesamol and sesame oil by DBD plasma treatment might enhance biological properties.