2-(2-Carboxymethyl-3-methylbenzyl)-4-methylindan-1-on | 183545-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(2-Carboxymethyl-3-methylbenzyl)-4-methylindan-1-on
• 英文别名: Methyl 2-methyl-6-((4-methyl-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)benzoate；methyl 2-methyl-6-[(7-methyl-3-oxo-1,2-dihydroinden-2-yl)methyl]benzoate
• CAS: 183545-69-9
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: ZRYSMRATPQWEPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-Carboxymethyl-3-methylbenzyl)-4-methylindan-1-on 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 异丙醇 为溶剂， 反应 6.0h， 生成 2-(2-Methoxycarbonyl-3-methylbenzyl)-4-methylindan
  参考文献：
  名称：

  Aromatische Spirane, 23. Mitt.: Darstellung von unsymmetrisch substituierten Dimethyl-2,2?-Spirobiindan-1,1?-dionen

  摘要：

  Both spirodiketones 7 and 8 were obtained as a mixture (56:44) by treatment of dicarbonic acid 5 with polyphosphoric acid (PPA). 5 was accessible from dimethylester 3, synthesized by retro-Claisen reaction between 1 and 2. In the same way, 30 was obtained via 27. The preparation of the pure spiro compounds 7 and 8, resp., was achieved by aldol reaction between 9 and 10 or 9 and 16, resp. Short treatment of the resulting compounds 11 and 17 with diazomethane yielded the methylbenzoates 12 and 18. Prolonged reaction (several hours) gave the pyrazole compounds 14 and 19, resp., which were also obtained (several days) from phthalides 14 and 20. The latter were formed from the benzylidene compounds 11 and 17, resp., by heating. 11 and 17 (after hydrogenation to 15a and 21a) were cyclized either with PPA or thermically to the spiro compounds 7 and 8. The main product 20 was cyclized thermically to 8 after reduction with zinc to a mixture of 21a and 8 (20:75).

  DOI：

  10.1007/bf00810885
• 作为产物：
  描述：

  4-甲基-1-茚酮 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 2-(2-Carboxymethyl-3-methylbenzyl)-4-methylindan-1-on
  参考文献：
  名称：

  Aromatische Spirane, 23. Mitt.: Darstellung von unsymmetrisch substituierten Dimethyl-2,2?-Spirobiindan-1,1?-dionen

  摘要：

  Both spirodiketones 7 and 8 were obtained as a mixture (56:44) by treatment of dicarbonic acid 5 with polyphosphoric acid (PPA). 5 was accessible from dimethylester 3, synthesized by retro-Claisen reaction between 1 and 2. In the same way, 30 was obtained via 27. The preparation of the pure spiro compounds 7 and 8, resp., was achieved by aldol reaction between 9 and 10 or 9 and 16, resp. Short treatment of the resulting compounds 11 and 17 with diazomethane yielded the methylbenzoates 12 and 18. Prolonged reaction (several hours) gave the pyrazole compounds 14 and 19, resp., which were also obtained (several days) from phthalides 14 and 20. The latter were formed from the benzylidene compounds 11 and 17, resp., by heating. 11 and 17 (after hydrogenation to 15a and 21a) were cyclized either with PPA or thermically to the spiro compounds 7 and 8. The main product 20 was cyclized thermically to 8 after reduction with zinc to a mixture of 21a and 8 (20:75).

  DOI：

  10.1007/bf00810885