(S)-ethyl 1-hydroxy-2-oxocyclopentanecarboxylate | 1141700-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-ethyl 1-hydroxy-2-oxocyclopentanecarboxylate
• 英文别名: ethyl 2-hydroxycyclopentanone-2-carboxylate；ethyl (1S)-1-hydroxy-2-oxocyclopentane-1-carboxylate
• CAS: 1141700-04-0
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: ICBBCTSZGFAHNS-QMMMGPOBSA-N

物化性质

• 沸点：
  260.9±40.0 °C(predicted)
• 密度：
  1.277±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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-氧代环戊羧酸乙酯 在 R-3,3'-二(三苯基硅基)联萘酚膦酸酯 、 4-氯亚硝基苯 作用下， 以 苯 为溶剂， 以83%的产率得到(S)-ethyl 1-hydroxy-2-oxocyclopentanecarboxylate
  参考文献：
  名称：

  Lu, Min; Zhu, Di; Lu, Yunpeng, Journal of the American Chemical Society, 2009, vol. 131, p. 4562 - 4563

  摘要：

  DOI：

文献信息

• Palladium-catalysed enantioselective α-hydroxylation of β-ketoesters
  作者：Alexander M. R. Smith、Denis Billen、King Kuok (Mimi) Hii

  DOI：10.1039/b907151b

  日期：——

  Highly enantioselective α-hydroxylation of cyclic and acyclic 1,3-ketoesters can be achieved with up to 98% ee using a dicationic palladium(II) catalyst and dimethyldioxirane as oxidant.

  使用双阳离子钯(II) 催化剂和二甲基二氧杂环己烷作为氧化剂，可以实现环状和无环1,3-酮酯的高度对映选择性α-羟基化，EE 高达 98%。
• Delineating Origins of Stereocontrol in Asymmetric Pd-Catalyzed α-Hydroxylation of 1,3-Ketoesters
  作者：Alexander M. R. Smith、Henry S. Rzepa、Andrew J. P. White、Denis Billen、King Kuok (Mimi) Hii

  DOI：10.1021/jo1002906

  日期：2010.5.7

  Systematic studies of reaction conditions and subsequent optimization led to the identification of important parameters for stereoselectivity in the asymmetric alpha-hydroxylation reaction of 1,3-ketoesters. Enantioselectivities of up to 98% can be achieved for cyclic substrates and 88% for acyclic ketoesters. Subsequently, the combination of cyclic/acyclic ketoester, catalyst, and oxidant was found to have a profound effect on reaction rates and turnover-limiting steps. The stereochemistry of the reaction contradicts that observed for other similar electrophilic substitution reactions. This was rationalized by transition-state modeling, which revealed a number of cooperative weak interactions between oxidant, ligand, and counterion, together with C-H/pi interactions that cumulatively account for the unusual stereoselectivity.