3,5-dimethyl-1H-indene-2-carboxylic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 3,5-dimethyl-1H-indene-2-carboxylic acid
• 英文别名: 3,5-dimethyl-indene-2-carboxylic acid
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: GYNRSVPBBSCRSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  3,5-dimethyl-1H-indene-2-carboxylic acid 生成 5-[(1R,2R)-1,6-dimethyl-2,3-dihydro-1H-inden-2-yl]-1H-imidazole;hydrochloride
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-methylbenzyl)-3-oxobutyric acid ethyl ester 在 硫酸 作用下， 以59%的产率得到3,5-dimethyl-1H-indene-2-carboxylic acid
  参考文献：
  名称：

  4-dihydroinden-2-yl-, 4-tetrahydronaphth-2-yl-, and

  摘要：

  一种制备式##STR1##的取代咪唑的方法，其中X为--CH.sub.2 --，--CH.sub.2 CH.sub.2 --或--O--，R.sub.1为H，低烷基或低烯基，OCH.sub.3或OCH.sub.2 CH.sub.3，R.sub.2为H，CH.sub.3，CH.sub.2 CH.sub.3，OCH.sub.3或OH，R.sub.3为H，CH.sub.3，CH.sub.2 CH.sub.3，OCH.sub.3或Hal，R.sub.4为H，CH.sub.3，CH.sub.2 CH.sub.3，OCH.sub.3或Hal，Hal为卤素，它们的无毒酸盐具有有价值的药理活性，特别适用于作为选择性α2-受体拮抗剂。

  公开号：

  US04689339A1

文献信息

• AlBr₃-Mediated Tandem Cyclization–Carboxylation of Allenylbenzenes with CO₂ in the Presence of Pyridines
  作者：Shinya Tanaka、Masafumi Chiba、Yuki Saito、Takaya Yamamoto、Tetsutaro Hattori

  DOI：10.1246/bcsj.20160410

  日期：2017.4.15

  Indene-2-carboxylic acids are prepared from allenylbenzenes and CO2 by an AlBr3-mediated tandem reaction consisting of intramolecular Friedel–Crafts alkylation of allenylbenzenes and subsequent car...

  茚-2-羧酸是由丙二烯基苯和二氧化碳通过AlBr3介导的串联反应制备的，该反应包括丙二烯基苯的分子内Friedel-Crafts烷基化和随后的汽车...
• Cyclization of Arylacetoacetates to Indene and Dihydronaphthalene Derivatives in Strong Acids. Evidence for Involvement of Further Protonation of O,O-Diprotonated β-Ketoester, Leading to Enhancement of Cyclization
  作者：Hiroaki Kurouchi、Hiromichi Sugimoto、Yuko Otani、Tomohiko Ohwada

  DOI：10.1021/ja908749u

  日期：2010.1.20

  The chemical features, such as substrate stability, product distribution, and substrate generality, and the reaction mechanism of Bronsted superacid-catalyzed cyclization reactions of aromatic ring-containing acetoacetates (beta-ketoesters) were examined in detail. While two types of carbonyl cyclization are possible, i.e., keto cyclization and ester cyclization, the former was found to take place exclusively. The reaction constitutes an efficient method to synthesize indene and 3,4-dihydronapthalene derivatives. Acid-base titration monitored with C-13 NMR spectroscopy showed that the acetoacetates are fully O-1,O-3-diprotonated at H-0 = -11. While the five-membered ring cyclization of the arylacetoacetates proceeded slowly at H-0 = -11, a linear increase in the rate of the cyclization was found with increasing acidity in the high acidity region of H-0 = -11.8 to -13.3. Therefore, the O-1,O-3-diprotonated acetoacetates exhibited some cyclizing reactivity, but they are not the reactive intermediates responsible for the acceleration of the cyclization in the high acidity region. The reactive cationic species might be formed by further protonation (or protosolvation) of the O-1,O-3-diprotonated acetoacetates; i.e., they may be tricationic species. Thermochemical data on the acid-catalyzed cyclization of the arylacetoacetates showed that the activation energy is decreased significantly as compared with that of the related acid-catalyzed cyclization reaction of a compound bearing a single functional group, such as a ketone. These findings indicate that intervention of the trication contributes to the activation of the cyclization of arylacetoacetates in strong acid, and the electron-withdrawing nature of the O-protonated ester functionality significantly increases the electrophilicity of the ketone moiety.
• ——
  作者：KARJALAINEN A. J.、 VIRTANEN R. E.、 KURKELA K. O. A.、 KARJALAINEN A.

  DOI：——

  日期：——
• Substituted imidazole derivatives and their preparation and use
  申请人：Farmos-Yhtyma Oy

  公开号：EP0183492B1

  公开（公告）日：1989-11-15
• US4689339A
  申请人：——

  公开号：US4689339A

  公开（公告）日：1987-08-25