(5S) ethyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate | 848900-98-1

• 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: (5S) ethyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate
• 英文别名: ethyl 5-hydroxy-3-oxo-5-phenylpentanoate；ethyl (5S)-5-hydroxy-3-oxo-5-phenylpentanoate
• CAS: 848900-98-1
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: RWMIZRRUNPQFSQ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (5S) ethyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate 在 sodium hydroxide 作用下， 反应 0.33h， 以98%的产率得到(S)-4-hydroxy-6-phenyl-5,6-dihydro-2-pyrone
  参考文献：
  名称：

  Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates

  摘要：

  A simple and convenient method was reported for the preparation of optically active beta-hydroxy-beta-arylpropionates, delta-hydroxy-delta-aryl-beta-oxo-pentanoates and their butyryl derivatives via CRL-catalyzed hydrolysis. The optically active products are potential precursors of some chiral pharmaceuticals and natural products. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.059
• 作为产物：
  描述：

  (5S) ethyl δ-chloroacetyloxy-δ-phenyl-β-oxo-pentanoate 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (5S) ethyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate
  参考文献：
  名称：

  Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates

  摘要：

  A simple and convenient method was reported for the preparation of optically active beta-hydroxy-beta-arylpropionates, delta-hydroxy-delta-aryl-beta-oxo-pentanoates and their butyryl derivatives via CRL-catalyzed hydrolysis. The optically active products are potential precursors of some chiral pharmaceuticals and natural products. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.059

文献信息

• A Concise Total Synthesis of Diospongins A and B
  作者：Gowravaram Sabitha、Pannala Padmaja、Jhillu S. Yadav

  DOI：10.1002/hlca.200890242

  日期：2008.12

  The total synthesis of the diarylheptanoids (−)-diospongin A (1) and B (2) was achieved stereoselectively via the δ-lactone intermediate 6. The key reactions involved are a stereoselective reduction of β-keto ester and the Horner–Wadsworth–Emmons and intramolecular oxy-Michael reactions.

  所述二芳基庚的全合成（ - ） - diospongin A（1）和B（2）中的立体选择性地实现经由所述δ -内酯中间体6。涉及的关键反应是β-酮酯的立体选择性还原和霍纳-沃兹沃思-埃蒙斯分子内和分子内的氧-迈克尔反应。
• Organocatalytic Asymmetric Peroxidation of γ,δ-Unsaturated β-Keto Esters—A Novel Route to Chiral Cycloperoxides
  作者：Mary C. Hennessy、Hirenkumar Gandhi、Timothy P. O’Sullivan

  DOI：10.3390/molecules28114317

  日期：——

  A methodology for the asymmetric peroxidation of γ,δ-unsaturated β-keto esters is presented. Using a cinchona-derived organocatalyst, the target δ-peroxy-β-keto esters were obtained in high enantiomeric ratios of up to 95:5. Additionally, these δ-peroxy esters can be readily reduced to chiral δ-hydroxy-β-keto esters without impacting the β-keto ester functionality. Importantly, this chemistry opens

  介绍了 γ,δ-不饱和 β-酮酯的不对称过氧化方法。使用金鸡纳衍生的有机催化剂，以高达 95:5 的高对映体比例获得了目标 δ-过氧-β-酮酯。此外，这些 δ-过氧酯可以很容易地还原为手性 δ-羟基-β-酮酯，而不会影响 β-酮酯的功能。重要的是，这种化学通过一种新的 P2O5 介导的相应 δ-过氧-β-羟基酯的环化，为手性 1,2-二氧戊环（许多生物活性天然产物中的常见基序）开辟了一条简洁的途径。
• 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.