6-tert-Butylindan-4-carbonsaeure | 5020-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-tert-Butylindan-4-carbonsaeure
• 英文别名: 6-t-butylindane-4-carboxylic acid；6-tert-Butyl-indancarbonsaeure-(4)；6-(1,1-Dimethylethyl)-2,3-dihydro-1H-indene-4-carboxylic acid；6-tert-butyl-2,3-dihydro-1H-indene-4-carboxylic acid
• CAS: 5020-63-3
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: OUAGETWGIKLGEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  184.5-185.5 °C
• 沸点：
  335.7±41.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-tert-Butylindan-4-carbonsaeure 在 lithium aluminium tetrahydride 、 三氯化铝 、 硫酸 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 127.0h， 生成 (2,3-dihydro-1H-inden-4-yl)methanol
  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：

  茚满 在 三氯化铝 、 sodium hypobromide 作用下， 以 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 6-tert-Butylindan-4-carbonsaeure
  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

• 2-Substituted oxazolo[4,5-b]pyridine anti-inflammatory agents
  申请人：Merck & Co., Inc.

  公开号：US04011326A1

  公开（公告）日：1977-03-08

  Oxazolo[4,5-b]pyridine substituted in the 2-position with a polyhydrobicycloaryl group are topical anti-inflammatory agents. They are prepared by condensing a 2-amino-3-hydroxypyridine with the appropriate carboxylic compound.

  2-聚氢化双环芳基氧唑并[4,5-b]吡啶是一种局部抗炎药，其在2位被聚氢化双环芳基基团取代。该药物通过将2-氨基-3-羟基吡啶与适当的羧酸化合物缩合制备而成。
• Giovannini,E.; Rubanis,N., Helvetica Chimica Acta, 1966, vol. 49, p. 561 - 564
  作者：Giovannini,E.、Rubanis,N.

  DOI：——

  日期：——
• US4011326A
  申请人：——

  公开号：US4011326A

  公开（公告）日：1977-03-08
• 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.