ethyl 2-isopropyl-3-hydroxybutyrate | 152548-75-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl 2-isopropyl-3-hydroxybutyrate
• 英文别名: Ethyl (2S)-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
• CAS: 152548-75-9
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: ZWCVMXGWEOPJGH-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-异丙基乙酰乙酸乙酯 生成 ethyl 2-isopropyl-3-hydroxybutyrate 、 ethyl 2-isopropyl-3-hydroxybutyrate
  参考文献：
  名称：

  Derivatives of the product of Baker's yeast reduction of ethyl 2-alkyl 3-oxobutanoates as precursors of free radical chirons of the 2(S)-hydroxyalkyl moiety

  摘要：

  Baker's yeast reductions of ethyl 2-alkyl 3-oxobutanoates provided ethyl 2-alkyl 3(S)-hydroxybumnoates. Such compounds were used as sources for precursors of 2(S)-ethoxymethoxyalkyl radicals whose reactions towards halogen donors, tin hydride and methyl acrylate have been studied.

  DOI：

  10.1016/s0957-4166(00)80232-3

文献信息

• A recombinant ketoreductase tool-box. Assessing the substrate selectivity and stereoselectivity toward the reduction of β-ketoesters
  作者：Dunming Zhu、Chandrani Mukherjee、J. David Rozzell、Spiros Kambourakis、Ling Hua

  DOI：10.1016/j.tet.2005.10.044

  日期：2006.1

  The substrate selectivity and stereoselectivity of a series of ketoreductases were evaluated toward the reduction of two sets of beta-ketoesters. Both the structural variety at beta-position and the substituent at alpha-position greatly affected the activity and stereoselectivity of these ketoreductases. For the first set of beta-ketoesters, at least one ketoreductase was found that catalyzed the formation of either (D) or (L) enantiomer of beta-hydroxyesters from each substrate with high optical purity, with the only exception of ethyl (D)-3-hydroxy3-phenylpropionate. For the second set of beta-ketoesters with alpha-substituents, the situation is more complex. More commonly, a ketoreductase was found that formed one of the four diastereomers in optically pure form, with only a few cases in which enzymes could be found that formed two or more of the diastereomers in high optical purity. The continued development of new, more diverse ketoreductases will create the capability to produce a wider range of single diastereomers of 2-substituted-3-hydroxy acids and their derivatives. (c) 2005 Elsevier Ltd. All rights reserved.