2-甲氧基甲氧基-3-羟基联苯 | 256431-54-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲氧基甲氧基-3-羟基联苯
• 英文名称: 2-methoxymethoxy-3-hydroxybiphenyl
• 英文别名: 3-Phenyl-2-(methoxymethoxy)phenol；2-(Methoxymethoxy)-3-phenylphenol
• CAS: 256431-54-6
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: MIVWSFMEYLWFAP-UHFFFAOYSA-N

物化性质

• 沸点：
  359.3±37.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲氧基甲氧基-3-羟基联苯 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 2,3-二羟基联苯
  参考文献：
  名称：

  Directed ortho-metalation and Suzuki–Miyaura cross-coupling connections: regiospecific synthesis of all isomeric chlorodihydroxybiphenyls for microbial degradation studies of PCBs

  摘要：

  单氯DHBs 1a–d 和 2a–c 通过定向邻位金属化和铃木–宫浦交叉偶联的组合以良好的总体产率区域选择性合成。

  DOI：

  10.1039/a907279i
• 作为产物：
  描述：

  邻苯基苯酚 在 sodium hydroxide 、 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 2-甲氧基甲氧基-3-羟基联苯
  参考文献：
  名称：

  Combined Directed ortho Metalation/Suzuki−Miyaura Cross-Coupling Strategies. Regiospecific Synthesis of Chlorodihydroxybiphenyls and Polychlorinated Biphenyls

  摘要：

  The Directed ortho Metalation (DoM)/Suzuki-Miyaura cross-coupling strategy is applied for the regiospecific construction of all isomeric monochloro and selected dichloro and trichloro 2,3-dihydroxybiphenyls (DHBs). The combined methodology highlights iterative DoM processes, hindered Suzuki-Miyaura couplings, and advantages in diversity in approaches from commercial starting materials leading to provision of chloro-DHBs as single isomers in high purity and on a gram scale. The syntheis of several PCBs are also reported.

  DOI：

  10.1021/jo062543i

文献信息

• Elucidation of the catalytic mechanisms of the non-haem iron-dependent catechol dioxygenases: synthesis of carba-analogues for hydroperoxide reaction intermediates
  作者：Christopher J. Winfield、Zeyana Al-Mahrizy、Michael Gravestock、Timothy D. H. Bugg

  DOI：10.1039/b004265j

  日期：——

  The catalytic mechanisms of the non-haem iron-dependent intradiol and extradiol catechol dioxygenases are thought to involve transient hydroperoxide reaction intermediates, formed by reaction of a catechol substrate with dioxygen. The synthesis of carba-analogues of these intermediates is described in which the hydroperoxide functional group (–OOH) is replaced by a hydroxymethyl group (–CH2OH), and

  非血红素依赖铁的内二醇和外二醇儿茶酚双加氧酶的催化机理被认为涉及瞬时的氢过氧化物反应中间体，该中间体是由邻苯二酚底物与双氧反应形成的。描述了这些中间体的碳水化合物类似物的合成，其中氢过氧化物官能团（–OOH）被羟甲基（–CH 2 OH）取代，并且环己二酮骨架简化为环己酮。发现“近端”氢过氧化物的类似物（其中羟甲基相对于环轴向定位）充当了多余的二醇酶2,3-二羟基苯基丙酸酯1,2-二加氧酶的竞争性抑制剂（K i 0.7–7.6 mM）。 （MhpB）来自大肠杆菌，而羟甲基位于赤道的类似物则没有抑制作用。相反，测定与来自假单胞菌属物种的内二醇裂解的原儿茶酸3，4-二加氧酶的比较。仅显示含有赤道羟甲基基团的类似物（IC 50 9.5 mM）具有抑制作用。这些数据支持在二醇外儿茶酚二加氧酶机制中存在近端氢过氧化物中间体，并表明氢过氧化物反应中间体采用的构象可能是决定二醇外和二醇内双加氧酶反应特异性的重要决定因素。
• Bacterial Catabolism of Biphenyls: Synthesis and Evaluation of Analogues
  作者：Sven Nerdinger、Eugene Kuatsjah、Timothy E. Hurst、Inge Schlapp-Hackl、Volker Kahlenberg、Klaus Wurst、Lindsay D. Eltis、Victor Snieckus

  DOI：10.1002/cbic.201800231

  日期：2018.8.16

  Alkylated 2,3‐dihydroxybiphenyls (DHBs) have been prepared on the gram scale by using a Directed ortho Metalation–Suzuki–Miyaura coupling strategy. These compounds were used to investigate the substrate specificity of the meta‐cleavage dioxygenase BphC, a key enzyme in the microbial catabolism of biphenyl. Isolation of the meta‐cleavage products will allow further study of the catabolism of lignin‐derived

  烷基化的2,3-二羟基联苯（地区保健委员会）已通过使用有向制备的克规模邻金属化-铃木-宫浦偶联策略。这些化合物用于研究间位裂解双加氧酶BphC（联苯微生物分解代谢中的关键酶）的底物特异性。分离元裂解产物将有助于进一步研究木质素衍生联苯的分解代谢。
• Combined Directed <b><i>ortho</i></b> Metalation/Suzuki−Miyaura Cross-Coupling Strategies. Regiospecific Synthesis of Chlorodihydroxybiphenyls and Polychlorinated Biphenyls
  作者：S. Nerdinger、C. Kendall、X. Cai、R. Marchart、P. Riebel、M. R. Johnson、C.-F. Yin、N. Hénaff,、L. D. Eltis、V. Snieckus

  DOI：10.1021/jo062543i

  日期：2007.8.1

  The Directed ortho Metalation (DoM)/Suzuki-Miyaura cross-coupling strategy is applied for the regiospecific construction of all isomeric monochloro and selected dichloro and trichloro 2,3-dihydroxybiphenyls (DHBs). The combined methodology highlights iterative DoM processes, hindered Suzuki-Miyaura couplings, and advantages in diversity in approaches from commercial starting materials leading to provision of chloro-DHBs as single isomers in high purity and on a gram scale. The syntheis of several PCBs are also reported.
• Directed ortho-metalation and Suzuki–Miyaura cross-coupling connections: regiospecific synthesis of all isomeric chlorodihydroxybiphenyls for microbial degradation studies of PCBs
  作者：S. Nerdinger、R. Marchhart、P. Riebel、C. Kendall、M. R. Johnson、C.-F. Yin、V. Snieckus、L. D. Eltis

  DOI：10.1039/a907279i

  日期：——

  Monochloro DHBs 1a–d and 2a–c have been regioselectively synthesised in good overall yields by a combination of directed ortho metalation and Suzuki–Miyaura cross-coupling.

  单氯DHBs 1a–d 和 2a–c 通过定向邻位金属化和铃木–宫浦交叉偶联的组合以良好的总体产率区域选择性合成。