Ethyl (1R^*,2R^*)-2-hydroxy-1,2-dimethyl-3-oxocyclopentanecarboxylate | 123187-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl (1R^*,2R^*)-2-hydroxy-1,2-dimethyl-3-oxocyclopentanecarboxylate
• 英文别名: ethyl (1S,2S)-2-hydroxy-1,2-dimethyl-3-oxocyclopentane-1-carboxylate
• CAS: 123187-59-7
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: SUNWHLGKDCHWCZ-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-acetyl-4-cyano-2-methyl-butyric acid ethyl ester 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以65%的产率得到Ethyl (1R^*,2R^*)-2-hydroxy-1,2-dimethyl-3-oxocyclopentanecarboxylate
  参考文献：
  名称：

  Intramolecular Ketone−Nitrile Reductive Coupling Reactions Promoted by Samarium(II) Iodide

  摘要：

  Samarium(II) iodide (SmI2) has been successfully utilized as a reducing agent for the intramolecular coupling of ketones with nitriles. The use of visible light to promote the reductive coupling represents an improvement over previously reported protocols. The procedure also avoids overreduction of the resulting alpha-hydroxy ketones. Monocyclic, fused bicyclic, and bridged bicyclic alpha-hydroxy ketones composed of a number of substitution patterns have been synthesized in moderate to excellent yield via this method. A sequential reaction consisting of a nucleophilic acyl substitution followed by a ketyl-nitrile coupling has also been accomplished.

  DOI：

  10.1021/jo981537m

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。
• Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Naoto Tominaga、Hiroshi Morita

  DOI：10.1021/jo00052a036

  日期：1992.12

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.