2-Carboxymethyl-6,7-dimethyl-indan-1-on | 177166-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-Carboxymethyl-6,7-dimethyl-indan-1-on
• 英文别名: Methyl 4,5-dimethyl-3-oxo-1,2-dihydroindene-2-carboxylate
• CAS: 177166-08-4
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: FHFRXBXDBAGIGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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-Carboxymethyl-6,7-dimethyl-indan-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 14.0h， 以95%的产率得到2-Carboxymethyl-4,5-dimethylindan
  参考文献：
  名称：

  Aromatische Spirane, 20. Mitt.: Darstellung von dimethylsubstituierten 2-Carboxymethyl-indan-1-onen und Benzylchloriden als Synthone f�r Synthesen von di- bis tetramethylierten 2,2?-Spirobiindandionen

  摘要：

  The isomeric dimethyl methylbenzoates 5, obtained from the bromides via Grignard reactions with dimethylcarbonate, were reduced with LiAlH4 to the hydroxymethyl derivatives 6. The latter were then transformed both to the benzylchlorides 7 (with SOCl2) and to the aldehydes 8 (with pyridinium chlorochromate). Knoevenagel-Doebner reaction of 8 afforded the acrylic acids 9 which (after hydrogenation to 11) were cyclized to the desired indanones 12 with polyphosphoric acid. On the other hand, 12c and 12e were prepared from dimethyl 3-chloropropiophenone (14) by warming with sulfuric acid. After NaH-catalyzed reaction with dimethylcarbonate, the indanones 12 gave the ketoesters 15 which then could be hydrogenated to the indanes 16. All reactions proceeded with satisfactory to excellent yields (60-90%).

  DOI：

  10.1007/bf00807400
• 作为产物：
  描述：

  3,4-二甲基苯甲酸甲酯 在 palladium on activated charcoal 哌啶 、 吡啶 、 lithium aluminium tetrahydride 、 PPA 、 氢气 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 25.0~80.0 ℃ 、206.84 kPa 条件下， 反应 73.5h， 生成 2-Carboxymethyl-6,7-dimethyl-indan-1-on
  参考文献：
  名称：

  Aromatische Spirane, 20. Mitt.: Darstellung von dimethylsubstituierten 2-Carboxymethyl-indan-1-onen und Benzylchloriden als Synthone f�r Synthesen von di- bis tetramethylierten 2,2?-Spirobiindandionen

  摘要：

  The isomeric dimethyl methylbenzoates 5, obtained from the bromides via Grignard reactions with dimethylcarbonate, were reduced with LiAlH4 to the hydroxymethyl derivatives 6. The latter were then transformed both to the benzylchlorides 7 (with SOCl2) and to the aldehydes 8 (with pyridinium chlorochromate). Knoevenagel-Doebner reaction of 8 afforded the acrylic acids 9 which (after hydrogenation to 11) were cyclized to the desired indanones 12 with polyphosphoric acid. On the other hand, 12c and 12e were prepared from dimethyl 3-chloropropiophenone (14) by warming with sulfuric acid. After NaH-catalyzed reaction with dimethylcarbonate, the indanones 12 gave the ketoesters 15 which then could be hydrogenated to the indanes 16. All reactions proceeded with satisfactory to excellent yields (60-90%).

  DOI：

  10.1007/bf00807400

文献信息

• Aromatische Spirane, 20. Mitt.: Darstellung von dimethylsubstituierten 2-Carboxymethyl-indan-1-onen und Benzylchloriden als Synthone f�r Synthesen von di- bis tetramethylierten 2,2?-Spirobiindandionen
  作者：H. K. Neudeck

  DOI：10.1007/bf00807400

  日期：1996.2

  The isomeric dimethyl methylbenzoates 5, obtained from the bromides via Grignard reactions with dimethylcarbonate, were reduced with LiAlH4 to the hydroxymethyl derivatives 6. The latter were then transformed both to the benzylchlorides 7 (with SOCl2) and to the aldehydes 8 (with pyridinium chlorochromate). Knoevenagel-Doebner reaction of 8 afforded the acrylic acids 9 which (after hydrogenation to 11) were cyclized to the desired indanones 12 with polyphosphoric acid. On the other hand, 12c and 12e were prepared from dimethyl 3-chloropropiophenone (14) by warming with sulfuric acid. After NaH-catalyzed reaction with dimethylcarbonate, the indanones 12 gave the ketoesters 15 which then could be hydrogenated to the indanes 16. All reactions proceeded with satisfactory to excellent yields (60-90%).

表征谱图