5-(1-Hydroxy-1-methyl-ethyl)-indan-2,2-dicarboxylic acid dimethyl ester | 136944-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-(1-Hydroxy-1-methyl-ethyl)-indan-2,2-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 5-(2-hydroxypropan-2-yl)-1,3-dihydroindene-2,2-dicarboxylate
• CAS: 136944-63-3
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: KOQBSKLIWHURFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-(2-bromo-allyl)-2-(prop-2-ynyl)-malonic acid dimethyl ester 在 palladium diacetate 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 生成 5-(1-Hydroxy-1-methyl-ethyl)-indan-2,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Palladium-catalyzed tandem bond forming reaction leading to aromatic ring through diene-yne system

  摘要：

  A double cyclization involving palladium-catalyzed intramolecular followed by intermolecular carbon-carbon bond formations starting from vinyl bromides with acetylenes produced aromatic compounds through diene-yne system in high yields.

  DOI：

  10.1016/s0040-4039(00)79893-5

文献信息

• Iridium Complex-Catalyzed [2+2+2] Cycloaddition of α,ω-Diynes with Monoynes and Monoenes
  作者：Satoko Kezuka、Shigeru Tanaka、Toshihito Ohe、Yoshihiko Nakaya、Ryo Takeuchi

  DOI：10.1021/jo051874c

  日期：2006.1.1

  [Ir(cod)Cl](2)/DPPE was found to be a new catalyst for the cycloaddition of alpha,omega-diynes with monoynes to give polysubstituted benzene derivatives in high yields. Internal monoynes as well as terminal monoynes could be used. The reaction tolerates a broad range of functional groups such as alcohol, amine, alkene, ether, halogen, and nitrile. The reaction of 1,6-octadiyne derivatives with 1-alkynes gives ortho products and meta products. The regioselectivity could be controlled by the choice of ligand. The reaction with DPPE was meta selective, with meta selectivity of up to 82%. The reaction with DPPF was ortho selective, with ortho selectivity of up to 88%. We propose a mechanism to account for this regioselective cycloaddition. [Ir(cod)Cl-2]2/DPPE also catalyzed the cycloaddition of alpha-omega-diynes with 2,5-dihydrofuran to give bicyclic cyclohexadiene derivatives. The reaction with 2,3-dihydrofuran and n-butyl vinyl ether gave benzene derivatives instead of cyclohexadiene derivatives. We also propose a mechanism to account for this novel aromatization that includes cleavage of the C-O bond.
• Palladium-catalyzed tandem bond forming reaction leading to aromatic ring through diene-yne system
  作者：Sigeru Torii、Hiroshi Okumoto、Akihiko Nishimura

  DOI：10.1016/s0040-4039(00)79893-5

  日期：1991.8

  A double cyclization involving palladium-catalyzed intramolecular followed by intermolecular carbon-carbon bond formations starting from vinyl bromides with acetylenes produced aromatic compounds through diene-yne system in high yields.