2-羟基环戊酮-2-羧酸叔丁酯 | 923569-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-羟基环戊酮-2-羧酸叔丁酯
• 英文名称: tert-butyl 2-hydroxycyclopentanone-2-carboxylate
• 英文别名: Tert-butyl (S)-1-hydroxy-2-oxocyclopentane-1-carboxylate；tert-butyl (1S)-1-hydroxy-2-oxocyclopentane-1-carboxylate
• CAS: 923569-28-2
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: VIJMSAOJQPQRFZ-JTQLQIEISA-N

物化性质

• 沸点：
  280.1±40.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 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：

  tert-butyl 2-oxocyclopentanecarboxylate 在 [(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]-diaquo-palladium(II) bis(triflate) 、 二甲基二环氧乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以88%的产率得到2-羟基环戊酮-2-羧酸叔丁酯
  参考文献：
  名称：

  Palladium-catalysed enantioselective α-hydroxylation of β-ketoesters

  摘要：

  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%。

  DOI：

  10.1039/b907151b

文献信息

• Iron(iii)–salan complexes catalysed highly enantioselective fluorination and hydroxylation of β-keto esters and N-Boc oxindoles
  作者：Xin Gu、Yan Zhang、Zhen-Jiang Xu、Chi-Ming Che

  DOI：10.1039/c4cc01631a

  日期：——

  Chiral iron(III)–salan complexes catalysed highly enantioselective α-fluorination and α-hydroxylation of β-keto esters and N-Boc oxindoles to give the corresponding products in high yields and good-to-excellent ee values under mild reaction conditions.

  手性铁(III)–salan复合物催化了β-酮酯和N-Boc氧杂环戊烯的高度对映选择性α-氟化和α-羟基化反应，在温和的反应条件下获得相应产物，产率高，对映体过量值良好至优异。
• 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.