(1S,2R)-2-Methyl-5-oxo-cyclopentanecarboxylic acid benzyl ester | 144407-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R)-2-Methyl-5-oxo-cyclopentanecarboxylic acid benzyl ester
• 英文别名: benzyl (1S,2R)-2-methyl-5-oxocyclopentane-1-carboxylate
• CAS: 144407-31-8
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: KJQJPZUXPHDPBD-MFKMUULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  巴豆醛 、 (1S,2R)-2-Methyl-5-oxo-cyclopentanecarboxylic acid benzyl ester 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 15.0h， 生成 (1S,2R)-2-Methyl-1-((R)-1-methyl-3-oxo-propyl)-5-oxo-cyclopentanecarboxylic acid benzyl ester 、 (1S,2R)-2-Methyl-1-((S)-1-methyl-3-oxo-propyl)-5-oxo-cyclopentanecarboxylic acid benzyl ester
  参考文献：
  名称：

  Ouvrard, Nicole; Rodriguez, Jean; Santelli, Maurice, Angewandte Chemie, 1992, vol. 104, # 12, p. 1658 - 1660

  摘要：

  DOI：

文献信息

• Very mild and efficient one-pot access to the valuable 2-hydroxybicyclo[3.2.1]octan-8-one ring system
  作者：Nicole Ouvrard、Philippe Ouvrard、Jean Rodriguez、Maurice Santelli

  DOI：10.1039/c39930000571

  日期：——

  Cyclic β-ketoesters undergo, in a one-pot process, a facile tandem Michael addition–regioselective aldol cyclization with α,β-unsaturated aldehydes in acetone at room temperature in the presence of 1.5 equiv. of K2CO3 to afford 2-hydroxybicyclo[3.2.1]octan-8-ones in synthetically useful yields.

  室温下，在 1.5 等量 K2CO3 的存在下，环状 β 酮在丙酮中与 α,β-不饱和醛发生简单的串联迈克尔加成-区域选择性醛醇环化反应，得到 2-羟基双环[3.2.1]辛烷-8-酮，合成收率高。
• One-Pot Base-Promoted Tandem Michael Addition-Intramolecular Aldolization. Stereoselective Synthesis and Reactivity of 2-Hydroxybicyclo[3.2.1]octan-8-ones
  作者：Marie-Helene Filippini、Robert Faure、Jean Rodriguez

  DOI：10.1021/jo00126a044

  日期：1995.10

  alpha-Substituted cyclopentanones 1 react with alpha,beta-unsaturated aldehydes 2 by a facile base-promoted (K2CO3, Cs2CO3, DBU) tandem Michael addition-intramolecular aldol cyclization to give, in synthetically useful yields (30-99%), highly substituted, stereodefined and optically active 2-hydroxybicyclo[3.2.1]octan-8-ones 3-19. A generally separable mixture of isomers, in which the one bearing an equatorial hydroxy group predominates, is obtained with simple aldehydes. In the case of prostereogenic Michael accepters one diastereomer usually prevails from as little as 75% to as much as >97%. This high axial-C-4 stereoselectivity results from a diastereoselective Michael addition and can be easily reversed by simple adaptation of the reaction conditions. The structures of the products rest upon NMR spectroscopy and chemical transformations. The synthetic potential of hydroxybicyclo[3.2.1]octanes is illustrated by transformations of 25-28, especially by their facile conversion to functionalized and stereodefined cycloheptanes 30, 32, 35-42.