methyl 5,7-dimethoxy-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylate | 914607-16-2

• 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: methyl 5,7-dimethoxy-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylate
• 英文别名: 1h-Isoindole-4-carboxylic acid,2,3-dihydro-5,7-dimethoxy-1-oxo-,methyl ester；methyl 5,7-dimethoxy-1-oxo-2,3-dihydroisoindole-4-carboxylate
• CAS: 914607-16-2
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: IUFAYMJFJTZFBA-UHFFFAOYSA-N

物化性质

• 熔点：
  228-235 °C(Solv: pentane (109-66-0))
• 沸点：
  516.3±50.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5,7-dimethoxy-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylate 在 三氯化硼 、 sodium hydride 、 1,2-二溴乙烷 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 methyl 5-{2,5-dimethoxy-3-[(4-methoxybenzyloxy)methyl]benzyl}-7-methoxy-2-methyl-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylate
  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：

  4,6-Dimethoxy-2-trifluoromethanesulfonyloxy-isophthalic acid dimethyl ester 在 platinum(IV) oxide 、 tris(dibenzylideneacetone)dipalladium (0) 1,1'-双(二苯基膦)二茂铁 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 40.0~60.0 ℃ 、482.63 kPa 条件下， 反应 6.0h， 生成 methyl 5,7-dimethoxy-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylate
  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.