garcibiphenyl C

• 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: garcibiphenyl C
• 英文别名: 3,5-dimethoxy-[1,1'-biphenyl]-4,4'-diol；Garcibiphenyl C；4-(4-hydroxyphenyl)-2,6-dimethoxyphenol
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: KMMVLPSUFLSVAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  C₂₁H₂₀O₄ 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 生成 garcibiphenyl C
  参考文献：
  名称：

  铁催化的溴酚与芳基格氏试剂的室温交叉偶联

  摘要：

  本文报道了各种溴酚与芳基格氏试剂的室温铁催化偶联反应，该反应具有较宽的底物范围和较高的官能团耐受性。首次将简单的Fe（acac）3 / PBu 3 / Ti（OEt）4的组合用作溴酚或其Na或K盐的联芳基偶联的有效催化剂，脱溴和醚化副反应很好压抑。使用本方案可轻松合成各种双酚，包括天然产物garbibiphenyl C以及药用双氟尼醛及其乙酯。

  DOI：

  10.1002/adsc.201900839

文献信息

• <i>meso</i>-Tetraphenylporphyrin Iron Chloride Catalyzed Selective Oxidative Cross-Coupling of Phenols
  作者：Hadas Shalit、Anna Libman、Doron Pappo

  DOI：10.1021/jacs.7b05898

  日期：2017.9.27

  A novel catalytic system for oxidative cross-coupling of readily oxidized phenols with poor nucleophilic phenolic partners based on an iron meso-tetraphenylporphyrin chloride (Fe[TPP]Cl) complex in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) was developed. The unique chemoselectivity of this reaction is attributed to the coupling between a liberated phenoxyl radical with an iron-ligated phenolic coupling

  基于 1,1,1,3,3,3-六氟丙烷-2 中的铁内消旋四苯基卟啉氯化物 (Fe[TPP]Cl) 络合物，用于易氧化酚与弱亲核酚伙伴的氧化交叉偶联的新型催化系统-ol (HFIP) 被开发出来。该反应独特的化学选择性归因于释放的苯氧基自由基与铁连接的酚偶联伙伴之间的偶联。这些条件可用于制备由被烷基或卤化物基团取代的反应性较低的酚单元组装而成的一长串不对称双酚。
• Suzuki–Miyaura Coupling of Halophenols and Phenol Boronic Acids: Systematic Investigation of Positional Isomer Effects and Conclusions for the Synthesis of Phytoalexins from Pyrinae
  作者：Bernd Schmidt、Martin Riemer

  DOI：10.1021/jo500675a

  日期：2014.5.2

  The Suzuki-Miyaura couplings of o-, m-, and p-halophenols with o-, m-, and p-phenol boronic acids were investigated for all combinations under standardized conditions, using Pd/C as a heterogeneous catalyst and water as a solvent. In the case of iodophenols, conventional heating was used, while for bromophenols significantly better results could be obtained using microwave irradiation. This systematic study revealed that 2,4'-biphenol is particularly difficult to access, irrespective of the starting materials used, but that these difficulties can be overcome by using different additives. The conclusions drawn from this investigation allowed us to identify conditions for the protecting group-free or minimized total synthesis of biaryl-type phytoalexins. These compounds possess antibacterial activity and are produced by fruit trees as a response to microbial infection.
• Iron‐Catalyzed Room Temperature Cross‐Couplings of Bromophenols with Aryl Grignard Reagents
  作者：Li‐Chen Xu、Kun‐Ming Liu、Xin‐Fang Duan

  DOI：10.1002/adsc.201900839

  日期：2019.12.3

  Herein we report a room temperature Fe‐catalyzed coupling reaction of various bromophenols with aryl Grignard reagents, which exhibits a wide substrate scope and high functional group tolerance. For the first time, the combination of simple Fe(acac)3/PBu3/Ti(OEt)4 has been used as an effective catalyst for the biaryl couplings of bromophenols or their Na or K salts with debromination and etherification

  本文报道了各种溴酚与芳基格氏试剂的室温铁催化偶联反应，该反应具有较宽的底物范围和较高的官能团耐受性。首次将简单的Fe（acac）3 / PBu 3 / Ti（OEt）4的组合用作溴酚或其Na或K盐的联芳基偶联的有效催化剂，脱溴和醚化副反应很好压抑。使用本方案可轻松合成各种双酚，包括天然产物garbibiphenyl C以及药用双氟尼醛及其乙酯。