(R)-5-hydroxy-3-oxo-5-phenyl-pentanoic acid tert-butyl ester | 849905-14-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (R)-5-hydroxy-3-oxo-5-phenyl-pentanoic acid tert-butyl ester
• 英文别名: t-butyl (R)-5-hydroxy-3-oxo-5-phenylpentanoate；t-butyl 5-hydroxy-3-oxo-5-phenylpentanoate；tert-butyl (5R)-5-hydroxy-3-oxo-5-phenylpentanoate
• CAS: 849905-14-2
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: LSIVFPBKSRABCP-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-5-hydroxy-3-oxo-5-phenyl-pentanoic acid tert-butyl ester 在 sodium tetrahydroborate 、 三乙基硼 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (4S,6R)-4-hydroxy-6-phenyltetrahydropyran-2-one
  参考文献：
  名称：

  Asymmetric synthesis of (6R)-4-hydroxy-6-substituted-δ-lactones

  摘要：

  A novel approach for the asymmetric synthesis of (6R)-4-hydroxy-6-substituted-delta-lactones has been achieved using asymmetric reduction of a prochiral ketone in the presence of (S)-(-)-diphenyl-prolinol/borane as a key step. The enantiomeric purity of the products was determined by chiral GC. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2016.12.006
• 作为产物：
  描述：

  苯乙酮 在 sodium tetrahydroborate 、 正丁基锂 、 硼酸三甲酯 、 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 sodium hydride 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 4.92h， 生成 (R)-5-hydroxy-3-oxo-5-phenyl-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric synthesis of (6R)-4-hydroxy-6-substituted-δ-lactones

  摘要：

  A novel approach for the asymmetric synthesis of (6R)-4-hydroxy-6-substituted-delta-lactones has been achieved using asymmetric reduction of a prochiral ketone in the presence of (S)-(-)-diphenyl-prolinol/borane as a key step. The enantiomeric purity of the products was determined by chiral GC. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2016.12.006

文献信息

• The one-pot, multi-component construction of highly substituted tetrahydropyran-4-ones using the Maitland–Japp reaction
  作者：Paul A. Clarke、William H. C. Martin、Jason M. Hargreaves、Claire Wilson、Alexander J. Blake

  DOI：10.1039/b508252h

  日期：——

  A one-pot, multi-component reaction for the synthesis of highly substituted tetrahydropyran-4-ones, based on the long forgotten Maitland–Japp reaction has been realised. Two different aldehydes and a derivative of a β-ketoester can be condensed regioselectively in the presence of a Lewis acid to form tetrahydropyran-4-ones in excellent yields. The diastereoselectively of the reaction was found to be dependant upon the nature of the Lewis acid and the temperature at which the reaction was carried out. This procedure was also extended to the formation of tetrahydropyran-4-ones in greater than 95% enantiomeric excess.

  在被人们遗忘已久的 MaitlandâJapp 反应的基础上，一种用于合成高度取代的四氢吡喃-4-酮的单锅多组分反应得以实现。在路易斯酸的作用下，两种不同的醛和δ-酮的衍生物可以选择性地缩合生成四氢吡喃-4-酮，产量极高。研究发现，反应的非对映选择性取决于路易斯酸的性质和反应的温度。该方法还可用于生成对映体过量率超过 95% 的四氢吡喃-4-酮。
• Revisiting the Maitland–Japp reaction. Concise construction of highly functionalised tetrahydropyran-4-ones
  作者：Paul A. Clarke、William H. C. Martin、Jason M. Hargreaves、Claire Wilson、Alexander J. Blake

  DOI：10.1039/b416247a

  日期：——

  Application of modern synthetic methods to the Maitland–Japp reaction has provided a one pot, one step procedure for the efficient construction of highly substituted tetrahydropyran-4-ones.

  将现代合成方法应用于 MaitlandâJapp 反应，为高效构建高取代度的四氢吡喃-4-酮提供了一锅一步的程序。
• A convenient stereoselective synthesis of 5-hydroxy-3-oxoesters and 3-hydroxy-5-oxoesters
  作者：Anna Żądło-Dobrowolska、Joerg H. Schrittwieser、Barbara Grischek、Dominik Koszelewski、Wolfgang Kroutil、Ryszard Ostaszewski

  DOI：10.1016/j.tetasy.2017.05.005

  日期：2017.6

  A biocatalytic approach was employed for the asymmetric reduction of sterically demanding ketones to prepare 3-hydroxy-5-oxo-5-phenylpentanoates and 5-hydroxy-3-oxo-5-phenylpentanoates. Screening a collection of microorganisms led to the identification of stereocomplementary microbial strains that provide access to both enantiomers of 3-hydroxy-5-oxo-5-phenylpentanoates and 5-hydroxy-3-oxo-5-phenylpentanoates with high enantiomeric excess (up to 99% ee). Moreover, the application of Saccharomyces cerevisiae gave two diastereomers of 3,5-dihydroxy-5-phenylpentanoates with high enantiomeric excess (up to 99% ee). The applicability of the identified strains was demonstrated by transforming the obtained dihydroxy ester into the chemically valuable lactone (4S,6R)-tetrahydro-4-hydroxy-6-phenyl-pyran-2-one. (C) 2017 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of (6R)-4-hydroxy-6-substituted-δ-lactones
  作者：Ravindra D. Gaikwad、Monica D. Rane、Sujata V. Bhat

  DOI：10.1016/j.tetasy.2016.12.006

  日期：2017.1

  A novel approach for the asymmetric synthesis of (6R)-4-hydroxy-6-substituted-delta-lactones has been achieved using asymmetric reduction of a prochiral ketone in the presence of (S)-(-)-diphenyl-prolinol/borane as a key step. The enantiomeric purity of the products was determined by chiral GC. (C) 2016 Published by Elsevier Ltd.