3-(2-Carboxy-4-methylphenyl)-2-(2-methylbenzyl)propansaeure | 183545-65-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(2-Carboxy-4-methylphenyl)-2-(2-methylbenzyl)propansaeure
• 英文别名: 2-(2-Carboxy-3-(2-methylphenyl)propyl)-5-methylbenzoic acid；2-[2-carboxy-3-(2-methylphenyl)propyl]-5-methylbenzoic acid
• CAS: 183545-65-5
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: POVNCUGONRRCTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-Carboxy-4-methylphenyl)-2-(2-methylbenzyl)propansaeure 在 PPS 作用下， 反应 16.0h， 以72.5%的产率得到4,6'-Dimethyl-2,2'-spirobiindan-1,1'-dion
  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：

  邻甲基氯化苄 在 氢氧化钾 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 30.0h， 生成 3-(2-Carboxy-4-methylphenyl)-2-(2-methylbenzyl)propansaeure
  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

文献信息

• Aromatische Spirane, 23. Mitt.: Darstellung von unsymmetrisch substituierten Dimethyl-2,2?-Spirobiindan-1,1?-dionen
  作者：H. K. Neudeck

  DOI：10.1007/bf00810885

  日期：1996.4

  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).