2,3-bis-(methoxymethoxy)-1,1’-biphenyl | 256431-55-7

• 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: 2,3-bis-(methoxymethoxy)-1,1’-biphenyl
• 英文别名: 2,3-bis(methoxymethoxy)biphenyl；1,2-Bis(methoxymethoxy)-3-phenylbenzene
• CAS: 256431-55-7
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: GSJNJLBAAHFXCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-bis-(methoxymethoxy)-1,1’-biphenyl 在 盐酸 、 正丁基锂 、 四甲基乙二胺 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 3-氯-6-苯基苯-1,2-二醇
  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 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 2,3-bis-(methoxymethoxy)-1,1’-biphenyl
  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

• 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。