methyl 2-(2,3-dihydro-1H-inden-4-yl)acetate | 183721-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: methyl 2-(2,3-dihydro-1H-inden-4-yl)acetate
• CAS: 183721-68-8
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: BNYNYDWCTBOCJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-(2,3-dihydro-1H-inden-4-yl)acetate 在 吡啶 、 lithium aluminium tetrahydride 、 甲基碘化镁 、 氯化亚砜 、 magnesium 作用下， 以 乙醚 、 苯 为溶剂， 反应 23.0h， 生成 3-(4-Indanyl)-propansaeure
  参考文献：
  名称：

  Aromatische Spirane, 22. Mitt.: Darstellung von Cyclopenteno-4,5-indan-1-on und 2-Carboxymethyl-bzw. 4-Chlormethyl-indan als Synthone f�r Synthesen von anellierten 2,2?-Spirobiindanonen

  摘要：

  The title compounds were prepared as follows: tert.-butyl-indane (10) was formylated to give a 72:28 mixture of the aldehydes 23a and 23b which were submitted to a Knoevenagel-Doebner condensation to afford the cinnamonic acids 24. From the mixture, the pure stereoisomer 24a was obtained by one crystallization in 57% yield. Its methylester 27a could be quantitatively dealkylated to the methylester 8 by treatment with AlCl3 in toluene. Cyclization to the indanone 9 was then performed via the propionic acid 7 with polyphosphoric acid in 95% yield. From 9 the carboxymethyl derivative 30 was obtained by treatment with dimethylcarbonate and NaH. The second synthone 4-chlormethylindane (19) was prepared from the corresponding alcohol 18 (in 82% yield) which in turn could be obtained from methylester 17 by reduction with LiAlH4. The latter was accessible in 75% yield by dealkylation of ester 13.

  DOI：

  10.1007/bf00813793
• 作为产物：
  描述：

  3-[2-(羧甲基)苯基]丙酸 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 乙醚 、 异丙醇 为溶剂， 80.0 ℃ 、413.69 kPa 条件下， 反应 8.0h， 生成 methyl 2-(2,3-dihydro-1H-inden-4-yl)acetate
  参考文献：
  名称：

  Aromatische Spirane, 22. Mitt.: Darstellung von Cyclopenteno-4,5-indan-1-on und 2-Carboxymethyl-bzw. 4-Chlormethyl-indan als Synthone f�r Synthesen von anellierten 2,2?-Spirobiindanonen

  摘要：

  The title compounds were prepared as follows: tert.-butyl-indane (10) was formylated to give a 72:28 mixture of the aldehydes 23a and 23b which were submitted to a Knoevenagel-Doebner condensation to afford the cinnamonic acids 24. From the mixture, the pure stereoisomer 24a was obtained by one crystallization in 57% yield. Its methylester 27a could be quantitatively dealkylated to the methylester 8 by treatment with AlCl3 in toluene. Cyclization to the indanone 9 was then performed via the propionic acid 7 with polyphosphoric acid in 95% yield. From 9 the carboxymethyl derivative 30 was obtained by treatment with dimethylcarbonate and NaH. The second synthone 4-chlormethylindane (19) was prepared from the corresponding alcohol 18 (in 82% yield) which in turn could be obtained from methylester 17 by reduction with LiAlH4. The latter was accessible in 75% yield by dealkylation of ester 13.

  DOI：

  10.1007/bf00813793

文献信息

• Aromatische Spirane, 22. Mitt.: Darstellung von Cyclopenteno-4,5-indan-1-on und 2-Carboxymethyl-bzw. 4-Chlormethyl-indan als Synthone f�r Synthesen von anellierten 2,2?-Spirobiindanonen
  作者：M. Melmer、H. Neudeck

  DOI：10.1007/bf00813793

  日期：1996.3

  The title compounds were prepared as follows: tert.-butyl-indane (10) was formylated to give a 72:28 mixture of the aldehydes 23a and 23b which were submitted to a Knoevenagel-Doebner condensation to afford the cinnamonic acids 24. From the mixture, the pure stereoisomer 24a was obtained by one crystallization in 57% yield. Its methylester 27a could be quantitatively dealkylated to the methylester 8 by treatment with AlCl3 in toluene. Cyclization to the indanone 9 was then performed via the propionic acid 7 with polyphosphoric acid in 95% yield. From 9 the carboxymethyl derivative 30 was obtained by treatment with dimethylcarbonate and NaH. The second synthone 4-chlormethylindane (19) was prepared from the corresponding alcohol 18 (in 82% yield) which in turn could be obtained from methylester 17 by reduction with LiAlH4. The latter was accessible in 75% yield by dealkylation of ester 13.