Ethyl (1R^*,2S^*,3R^*)-1-ethyl-2-hydroxy-2,3-dimethylcyclopentanecarboxylate | 123187-61-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Ethyl (1R^*,2S^*,3R^*)-1-ethyl-2-hydroxy-2,3-dimethylcyclopentanecarboxylate
• 英文别名: ethyl (1RS,2SR,3RS)-1-ethyl-2-hydroxy-2,3-dimethylcyclopentanecarboxylate；ethyl (1S,2R,3S)-1-ethyl-2-hydroxy-2,3-dimethylcyclopentane-1-carboxylate
• CAS: 123187-61-1
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: IRVBSOOKWNKBKR-MVWJERBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Ethyl 2-acetyl-2-ethyl-5-hexenoate 在 1-methoxyethyl-3-methylimidazolium mesylate 作用下， 以 异丙醇 为溶剂， 以75%的产率得到Ethyl (1R^*,2S^*,3R^*)-1-ethyl-2-hydroxy-2,3-dimethylcyclopentanecarboxylate
  参考文献：
  名称：

  A new diastereoselective intramolecular electroreductive coupling of unsaturated β-ketoesters and β-ketoamides in ionic liquids at a tin cathode

  摘要：

  The diastereoselective intramolecular electroreductive coupling of several beta-ketoesters and beta-ketoamides has been accomplished at a tin cathode in ionic liquids and isopropanol (9:1). The ionic liquids used are 1-butyl-3-methylimidazolium bromide [BMIM]Br, 1-butyl-3-methylimidazolium tetrafluoroborate [BMIM]BF4, 1-methoxyethyl-3-methylimidazolium trifluoroacetate [MOEMIM]CF3COO and 1-methoxyethyl-3-methylimidazolium mesylate [MOEMIM]Ms. This methodology offers a clean and green process for the synthesis of functionalized carbocycles in good yields with excellent stereochemical control at three stereogenic centres. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.076

文献信息

• Intramolecular reductive coupling reactions promoted by samarium diiodide
  作者：Gary A. Molander、Caryn Kenny

  DOI：10.1021/ja00203a027

  日期：1989.10

  Samarium diiodide is a useful reagent for promoting intramolecular reductive coupling reactions, generating functionalized carbocycles. Ketone-olefin coupling, pinacolic coupling, and other related reductive coupling reactions are accomplished under mild conditions with samarium diiodide. Products are accessed in high yield, and in many cases excellent stereochemical control is achieved at three contiguous

  二碘化钐是促进分子内还原偶联反应、生成功能化碳环的有用试剂。酮-烯烃偶联、频哪醇偶联和其他相关的还原偶联反应是在温和条件下使用二碘化钐完成的。产品以高产率获得，并且在许多情况下在三个相邻的立体中心实现了出色的立体化学控制。讨论了控制这些反应立体化学结果的因素，并概述了机械方面的考虑。