5-hydroxyindan-2,2-dicarboxylic acid dimethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-hydroxyindan-2,2-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 5-hydroxy-1,3-dihydroindene-2,2-dicarboxylate；dimethyl 5-hydroxy-1,3-dihydroindene-2,2-dicarboxylate
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: AZIBPVANZLNDGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Dimethyl 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1,3-dihydroindene-2,2-dicarboxylate 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以93%的产率得到5-hydroxyindan-2,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of bi- and tricyclic arylboronates via Cp*RuCl-catalyzed cycloaddition of α,ω-diynes with ethynylboronate

  摘要：

  在存在5-10摩尔%的Cp*RuCl(cod)的情况下，1,6-和1,7-二炔与乙炔基硼酸盐在常温下反应，以64-93%的分离产率产生了双环和三环芳基硼酸盐。

  DOI：

  10.1039/b506977g

文献信息

• Intramolecular Reactions of Alkynes with Furans and Electron Rich Arenes Catalyzed by PtCl₂:  The Role of Platinum Carbenes as Intermediates
  作者：Belén Martín-Matute、Cristina Nevado、Diego J. Cárdenas、Antonio M. Echavarren

  DOI：10.1021/ja029125p

  日期：2003.5.1

  On the basis of DFT calculations, a cyclopropyl platinacarbene complex was found as the key intermediate in the process. The cyclopropane and dihydrofuran rings of this intermediate open to form a carbonyl compound, which reacts with the platinum carbene to form an oxepin, which is in equilibrium with an arene oxide. When the reaction is carried out in the presence of water, dicarbonyl compounds are

  5-(2-呋喃基)-1-炔烃与 PtCl(2) 作为催化剂反应生成苯酚。根据 DFT 计算，发现环丙基铂卡宾配合物是该过程的关键中间体。该中间体的环丙烷和二氢呋喃环开环形成羰基化合物，该化合物与铂卡宾反应形成氧杂环庚烷，其与芳烃氧化物处于平衡状态。当反应在水存在下进行时，得到二羰基化合物，这支持了所提出的机理。炔烃与呋喃或富电子芳烃的其他环化产生明显的弗里德尔-克拉夫茨型反应的产物，尽管这些过程也可以通过涉及环丙基铂卡宾形成的途径进行。
• Synthesis of arylboronates via Cp*RuCl-catalyzed cycloaddition of alkynylboronates
  作者：Yoshihiko Yamamoto、Kozo Hattori、Jun-ichi Ishii、Hisao Nishiyama

  DOI：10.1016/j.tet.2006.02.068

  日期：2006.5

  In the presence of 5-10 mol% Cp*RuCI(cod), 1,6- and 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bicyclic arylboronates in 64-93% isolated yields. 1,6-Diynes bearing a boronate terminal also underwent cycloaddition with monoalkynes to give the corresponding bicyclic arylboronates. (c) 2006 Elsevier Ltd. All rights reserved.
• PtII-Catalyzed Intramolecular Reaction of Furans with Alkynes
  作者：Belén Martín-Matute、Diego J. Cárdenas、Antonio M. Echavarren

  DOI：10.1002/1521-3773(20011217)40:24<4754::aid-anie4754>3.0.co;2-9

  日期：2001.12.17
• A New Route to Substituted Phenols by Cationic Rhodium(I)/BINAP Complex-Catalyzed Decarboxylative [2 + 2 + 2] Cycloaddition
  作者：Hiromi Hara、Masao Hirano、Ken Tanaka

  DOI：10.1021/ol900123d

  日期：2009.3.19

  A new route to substituted phenols has been developed by cationic rhodium(I)/BINAP complex-catalyzed decarboxylative [2 + 2 + 2] cycloadditions of 1,6- and 1,7-diynes with commercially available vinylene carbonate.