{2,5-dimethoxy-3-[(4-methoxybenzyloxy)methyl]phenyl}methanol | 914607-26-4

• 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: {2,5-dimethoxy-3-[(4-methoxybenzyloxy)methyl]phenyl}methanol
• 英文别名: [2,5-Dimethoxy-3-[(4-methoxyphenyl)methoxymethyl]phenyl]methanol
• CAS: 914607-26-4
• 化学式: C₁₈H₂₂O₅
• 分子量: 318.37
• InChiKey: XVWIFBRWDKFUSO-UHFFFAOYSA-N

物化性质

• 沸点：
  458.9±40.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {2,5-dimethoxy-3-[(4-methoxybenzyloxy)methyl]phenyl}methanol 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以73%的产率得到1-(bromomethyl)-2,5-dimethoxy-3-[(4-methoxybenzyloxy)methyl]benzene
  参考文献：
  名称：

  Studies on the Total Synthesis of Lactonamycin:  Synthesis of the CDEF Ring System

  摘要：

  A concise and efficient synthesis of the tetracyclic CDEF ring system of lactonamycin (1) is described. The key step involved the Lewis acid mediated, intramolecular Friedel-Crafts acylation of carboxylic acid 6 to produce the tetracyclic CDEF core structure of target 1. The synthesis of 6 was carried out using a high-yielding Negishi coupling of benzyl bromide 7 with triflate 8, which was accessible in 11 steps and 31% overall yield on a multigram scale starting from trihydroxy acid 9.

  DOI：

  10.1021/jo0613378
• 作为产物：
  描述：

  2,6-bis(hydroxymethyl)-4-methoxyphenol 在 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.0h， 生成 {2,5-dimethoxy-3-[(4-methoxybenzyloxy)methyl]phenyl}methanol
  参考文献：
  名称：

  Studies on the Total Synthesis of Lactonamycin:  Synthesis of the CDEF Ring System

  摘要：

  A concise and efficient synthesis of the tetracyclic CDEF ring system of lactonamycin (1) is described. The key step involved the Lewis acid mediated, intramolecular Friedel-Crafts acylation of carboxylic acid 6 to produce the tetracyclic CDEF core structure of target 1. The synthesis of 6 was carried out using a high-yielding Negishi coupling of benzyl bromide 7 with triflate 8, which was accessible in 11 steps and 31% overall yield on a multigram scale starting from trihydroxy acid 9.

  DOI：

  10.1021/jo0613378

文献信息

• Studies on the Total Synthesis of Lactonamycin:  Synthesis of the CDEF Ring System
  作者：Hermut Wehlan、Eva Jezek、Nathalie Lebrasseur、Grégoire Pavé、Emmanuel Roulland、Andrew J. P. White、Jeremy N. Burrows、Anthony G. M. Barrett

  DOI：10.1021/jo0613378

  日期：2006.10.1

  A concise and efficient synthesis of the tetracyclic CDEF ring system of lactonamycin (1) is described. The key step involved the Lewis acid mediated, intramolecular Friedel-Crafts acylation of carboxylic acid 6 to produce the tetracyclic CDEF core structure of target 1. The synthesis of 6 was carried out using a high-yielding Negishi coupling of benzyl bromide 7 with triflate 8, which was accessible in 11 steps and 31% overall yield on a multigram scale starting from trihydroxy acid 9.