5-[2,5-dimethoxy-3-(methoxymethyl)benzyl]-7-methoxy-2-methyl-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid | 914607-12-8

• 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: 5-[2,5-dimethoxy-3-(methoxymethyl)benzyl]-7-methoxy-2-methyl-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid
• 英文别名: 5-[[2,5-dimethoxy-3-(methoxymethyl)phenyl]methyl]-7-methoxy-2-methyl-1-oxo-3H-isoindole-4-carboxylic acid
• CAS: 914607-12-8
• 化学式: C₂₂H₂₅NO₇
• 分子量: 415.443
• InChiKey: HFFIEMDAIYSDMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-[2,5-dimethoxy-3-(methoxymethyl)benzyl]-7-methoxy-2-methyl-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid 在 Dimethyl-(2-methyl-3-chlor-allyl)-amin 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  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：

  1-(bromomethyl)-2,5-dimethoxy-3-(methoxymethyl)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 27.5h， 生成 5-[2,5-dimethoxy-3-(methoxymethyl)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