3'-羟基-5-甲氧基-3,4-亚甲二氧基联苯 | 136051-64-4

• 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: 3'-羟基-5-甲氧基-3,4-亚甲二氧基联苯
• 英文名称: 3'-hydroxy-5-methoxy-3,4-methylenedioxybiphenyl
• 英文别名: 3-(7-methoxybenzo[d][1,3]dioxol-5-yl)phenol；3-(7-Methoxy-1,3-benzodioxol-5-yl)phenol
• CAS: 136051-64-4
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: RZEQCWOSRBVTLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴-2-羟基-3-甲氧基苯甲醛 在 palladium 10% on activated carbon 、 双氧水 、 potassium carbonate 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3'-羟基-5-甲氧基-3,4-亚甲二氧基联苯
  参考文献：
  名称：

  Suzuki–Miyaura Coupling of Halophenols and Phenol Boronic Acids: Systematic Investigation of Positional Isomer Effects and Conclusions for the Synthesis of Phytoalexins from Pyrinae

  摘要：

  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.

  DOI：

  10.1021/jo500675a

文献信息

• 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.