dimethyl 2-benzoylcyclopentane-1,1-dicarboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 2-benzoylcyclopentane-1,1-dicarboxylate
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: SQYDHYXZVLSNHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-dimethyl 2-(5-oxo-5-phenylpentyl)malonate 在 potassium iodide 作用下， 以 甲醇 为溶剂， 以89%的产率得到dimethyl 2-benzoylcyclopentane-1,1-dicarboxylate
  参考文献：
  名称：

  Anodic cyclization of dimethyl 2-(5-aryl-5-oxopentyl)malonates into the corresponding dimethyl 2-aroylcyclopentane-1,1-dicarboxylates

  摘要：

  A wide range of dimethyl 2-(5-aryl-5-oxopentyl)malonates was electrooxidized in methanol, in the presence of catalytic amount of potassium iodide, to give the corresponding dimethyl 2-aroylcyclopentane-1,1-dicarboxylates in high yields.The reactions were carried out under extremely mild reaction conditions, in which the optimal amount of electrolytic current ranged from 2.24 to 2.35 Fmol(-1). The reaction presumably proceeded via a two-electron oxidation process, in which iodide ions played an important role as the electron carrier between the anode and the substrate. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.104

文献信息

• Intramolecular and Intermolecular Mn(III)-Induced Carbon Monoxide Trapping Reactions of Alkynes with Malonate and Cyano Ester Units
  作者：Kazumi Okuro、Howard Alper

  DOI：10.1021/jo9607673

  日期：1996.1.1

  Intra- and intermolecular carbon monoxide trapping reactions of alkynes with malonates and cyano esters were developed using a Mn(III)-induced oxidative system. Phenylacetylene was treated with diethyl ethylmalonate in the presence of Mn(OAc)(3) . 2H(2)O, in AcOH-CH3CN (1:1) under carbon monoxide, affording (Z)-4,4-dicarbethoxy-2-phenyl-2-hexenoic acid. Similarly, intramolecular reactions of 4-alkynylmalonates and cyanoacetates proceeded regio- and stereoselectively under the same conditions to afford the corresponding methylenecycloalkanecarboxylic acids in moderate yields. The reaction involves carbon monoxide trapping of vinyl radicals which are formed by the addition of malonate or cyanoacetate radicals induced by Mn(III) to alkynes.