(5R) methyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate | 220757-08-4

• 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: (5R) methyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate
• 英文别名: (5R)-5-hydroxy-3-oxo-5-phenylpentanoic acid methyl ester；5-(R)-phenyl-5-hydroxy-3-oxo-pentanoic acid methyl ester；5-hydroxy-3-oxo-5-phenyl pentanoic acid methyl ester；methyl (5R)-5-hydroxy-3-oxo-5-phenylpentanoate；(R)-methyl 5-hydroxy-3-oxo-5-phenylpentanoate
• CAS: 220757-08-4
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: QNJDSGDMHFINPN-LLVKDONJSA-N

物化性质

• 沸点：
  349.0±27.0 °C(predicted)
• 密度：
  1.187±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

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：

  (5R) methyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate 在 sodium hydroxide 作用下， 反应 0.33h， 以98%的产率得到(R)-3-hydroxy-butanoic acid methyl ester
  参考文献：
  名称：

  A Chemoenzymatic Approach to Optically Active 5-Hydroxy-3-oxo-carboxylates

  摘要：

  酶促水解被应用于某些手性5-羟基-3-氧基羧酸酯的制备，这些化合物是通过形成内酯衍生物和四氢吡喃环用于天然产物合成的潜在前体。

  DOI：

  10.1055/s-2004-817746
• 作为产物：
  描述：

  5-hydroxy-3-oxo-5-phenyl-valeric acid methyl ester 在 4-二甲氨基吡啶 、 水 、 N,N'-二环己基碳二亚胺 、 磷脂酶B 作用下， 以 二氯甲烷 、 异丙醚 为溶剂， 反应 24.0h， 生成 (5R) methyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate
  参考文献：
  名称：

  A Chemoenzymatic Approach to Optically Active 5-Hydroxy-3-oxo-carboxylates

  摘要：

  酶促水解被应用于某些手性5-羟基-3-氧基羧酸酯的制备，这些化合物是通过形成内酯衍生物和四氢吡喃环用于天然产物合成的潜在前体。

  DOI：

  10.1055/s-2004-817746

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).
• An efficient asymmetric aldol reaction of Chan's diene promoted by chiral Ti(IV)–BINOL complex
  作者：Annunziata Soriente、Margherita De Rosa、Marina Stanzione、Rosaria Villano、Arrigo Scettri

  DOI：10.1016/s0957-4166(01)00150-1

  日期：2001.4

  1.3-Bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene (Chan's diene) can be conveniently used in asymmetric aldol reaction with aromatic, heteroaromatic, alpha,beta -unsaturated and aliphatic aldehydes in the presence of catalytic amounts (2-8% mol) of chiral Ti(IV)/(R)-BINOL complex. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates
  作者：Chengfu Xu、Chengye Yuan

  DOI：10.1016/j.tet.2004.12.059

  日期：2005.2

  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.
• 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.