(5S) methyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate | 245344-29-0

• 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) methyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate
• 英文别名: methyl (5S)-5-hydroxy-3-oxo-5-phenylpentanoate
• CAS: 245344-29-0
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: QNJDSGDMHFINPN-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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) methyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate 在 zinc(II) tetrahydroborate 、 2-iodoxybenzoic acid 、 camphor-10-sulfonic acid 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  通过不对称的醛醇缩合反应全合成（-）-双甘氨酸A和（+）-cryptofolione

  摘要：

  基于从Chan's二烯开始的不对称醛醇缩合反应，已经描述了两个独特的吡喃酮骨架双皂甙A和隐叶酮的立体选择性合成。合成策略包括对映选择性Mukaiyama羟醛，非对映选择性还原δ-羟基-β-酮酸酯，一连串的脱保护序列以及分子内的oxa-Michael反应以获得双桥皂苷A以及使用闭环易位反应形成不对称的烯丙基化和内酯形成获得隐氟利酮。

  DOI：

  10.1016/j.tetlet.2010.12.070
• 作为产物：
  描述：

  (5S) methyl 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) methyl 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

• Nonlinear effects and auto-induction in the asymmetric aldol condensation of synthetic equivalents of acetoacetic esters
  作者：Rosaria Villano、Margherita De Rosa、Concetta Salerno、Annunziata Soriente、Arrigo Scettri

  DOI：10.1016/s0957-4166(02)00539-6

  日期：2002.9

  (+)-NLEs, have been detected in the Ti(IV)/BINOL complex-mediated catalytic asymmetric aldol reaction of three different masked acetoacetate esters. The use of a different procedure for the catalyst preparation disclosed the occurrence of aldol condensation of Chan's diene through an auto-inductive process.

  在三种不同掩蔽的乙酰乙酸酯的Ti（IV）/ BINOL络合物介导的催化不对称羟醛反应中已检测到正非线性效应（+）-NLE。使用不同的方法制备催化剂表明通过自动感应方法发生了陈氏二烯的醛醇缩合反应。
• A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions
  作者：Syun-ichi Kiyooka、Mostofa A. Hena

  DOI：10.1021/jo990342r

  日期：1999.7.1

  A shortening of the reaction path can be realized by using a series of the chiral oxazaborolidinone-promoted aldol reaction with respect to the practical synthesis of the (+)-acutiphycin seco acid derivative 5. The linear strategy is based on the utilization of five aldol reactions with a sequence of silyl nucleophiles, 7, 8, 35, 10, and 11, in the presence of stoichiometric amounts of the promoter, 1 or 2. The construction of the relative configuration between the stereogenic centers is diastereoselectively controlled by the stereochemistry of the promoter used in the enantioselective aldol reaction, which is nearly independent of that of the substrate (promoter control).
• Achiral additives dramatically enhance enantioselectivities in the BINOL–Ti(IV) complex catalyzed aldol condensations of aldehydes with Chan’s diene
  作者：Qinyao Xu、Jianghui Yu、Fengyan Han、Juan Hu、Weiping Chen、Liping Yang

  DOI：10.1016/j.tetasy.2010.01.008

  日期：2010.2

  Achiral additives can dramatically enhance the enantioselectivities in the BINOL-Ti(IV) complex catalyzed aldol condensations of aldehydes with Chan's diene. The best results were obtained by using 2.0 equiv of LiCl with respect to (S)-BINOL/Ti(Oi-Pr)(4) as the additive. In the presence of 4.0 mol % of LiCl and 2.0 mol % of BINOL/Ti(Oi-Pr)(4), all aldehydes tested gave delta-hydroxy-beta-ketoesters as almost pure single enantiomers. Moreover, the present catalyst system was highly effective on reducing the catalyst loadings to 0.1 mol %. Published by Elsevier Ltd.
• A new procedure for the enantioselective vinylogous aldol reaction of Chan’s diene
  作者：Rosaria Villano、Maria Rosaria Acocella、Antonio Massa、Laura Palombi、Arrigo Scettri

  DOI：10.1016/j.tetasy.2006.12.016

  日期：2006.12

  Chiral delta-hydroxy-delta-ketoesters are easily available through the enantio selective vinylogous aldol reaction of Chan's diene promoted by a SiCl4/chiral phosphoramide catalytic system. The procedure is conveniently exploited for a very rapid approach to (+)-kavain, a natural bio-active alpha-pyrone compound. (c) 2007 Elsevier Ltd. All rights reserved.
• Solvent-free asymmetric vinylogous aldol reaction of Chan's diene with aromatic aldehydes catalyzed by hydrogen bonding
  作者：Rosaria Villano、Maria Rosaria Acocella、Antonio Massa、Laura Palombi、Arrigo Scettri

  DOI：10.1016/j.tet.2009.01.112

  日期：2009.7

  Chan's diene proved to react with aromatic aldehydes under organocatalytic conditions in presence of a chiral naphthyl-TADDOL derivative to give vinylogous aldols (up to 65% ee) with complete gamma-selectivity. A further process of hetero-Diels-Alder cycloaddition, leading to chiral pyran-4-one derivatives (up to 60% ee), was favoured by electron-withdrawing substituents on the aromatic ring. (C) 2009 Elsevier Ltd. All rights reserved.