1-(bromomethyl)-2,5-dimethoxy-3-[(4-methoxybenzyloxy)methyl]benzene | 914607-34-4

• 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: 1-(bromomethyl)-2,5-dimethoxy-3-[(4-methoxybenzyloxy)methyl]benzene
• 英文别名: 1-(Bromomethyl)-2,5-dimethoxy-3-[(4-methoxyphenyl)methoxymethyl]benzene
• CAS: 914607-34-4
• 化学式: C₁₈H₂₁BrO₄
• 分子量: 381.266
• InChiKey: HKHRDMUAJZHQMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(bromomethyl)-2,5-dimethoxy-3-[(4-methoxybenzyloxy)methyl]benzene 在 lithium hydroxide 、 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 30.0h， 生成 5-{2,5-dimethoxy-3-[(4-methoxybenzyloxy)methyl]benzyl}-7-methoxy-2-methyl-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid
  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：

  {2,5-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

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.