(S)-3-methyl-5-oxo-5-phenyl-pentanoic acid methyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-methyl-5-oxo-5-phenyl-pentanoic acid methyl ester
• 英文别名: methyl (3S)-3-methyl-5-oxo-5-phenylpentanoate；(S)-methyl 3-methyl-5-oxo-5-phenylpentanoate；methyl (S)-3-methyl-5-oxo-5-phenylpentanoate
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: ALNDZUCXUVJBGY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 4-bromo-3-methylbut-2-enoate 在 lithium aluminium tetrahydride 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-3-methyl-5-oxo-5-phenyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Biocatalyzed preparation of the optically enriched stereoisomers of 4-methyl-2-phenyl-tetrahydro-2H-pyran (Doremox^®)

  摘要：

  使用逆向翻译技术，将英文翻译成中文： 通过适当衍生物的对映选择性面包酵母还原和脂肪酶介导的动力学分辨法，制备了玫瑰氧化物类似物Doremox®的四种立体异构体，其对映体富集。关键词：酵母，脂肪酶，气味剂，还原，动力学分辨。

  DOI：

  10.1139/v02-042

文献信息

• Asymmetric Conjugate Addition of Silyl Enol Ethers Catalyzed by Tethered Bis(8-quinolinolato) Aluminum Complexes
  作者：Norito Takenaka、Joshua P. Abell、Hisashi Yamamoto

  DOI：10.1021/ja0668320

  日期：2007.1.1

  aluminum(III) complexes effectively catalyze the highly enantioselective Mukaiyama−Michael reaction of silyl enol ethers, including tetrasubstituted enolates that give rise to enantioenriched α-carbonyl all-carbon-substituted quaternary stereocenters. The present catalyst also promotes the conjugate addition of N-benzylindole to α,β-unsaturated acylphosphonates with high enantioselectivity (indole Friedel−Crafts

  新的手性系链双（8-羟基喹啉）（TBOx）铝（III）配合物有效催化甲硅烷基烯醇醚的高度对映选择性 Mukaiyama-Michael 反应，包括产生对映体富集的 α-羰基全碳取代四元立体中心的四取代烯醇化物。本催化剂还促进了 N-苄基吲哚与具有高对映选择性的 α,β-不饱和酰基膦酸酯的共轭加成（吲哚 Friedel-Crafts 烷基化反应）。
• The preparation of novel chiral auxiliaries SAMIQ/RAMIQ and their application in the asymmetric Michael addition
  作者：Xuan Pan、Zhanzhu Liu

  DOI：10.1016/j.tet.2014.05.049

  日期：2014.8

  A pair of novel chiral auxiliaries SAMIQ/RAMIQ was synthesized from L- or D-phenylalanine methyl ester hydrochloride over six steps in 45.8% and 44.4% yield, respectively. The SAMIQ-/RAMIQ-hydrazone methodology was applied for the asymmetric Michael addition of ketones to alpha,beta-unsaturated carboxylic acid methyl esters, which afforded 3-substituted-5-oxo-alkanoates in moderate to good yield (65-82%) with excellent enantioselectivity (ee=95.3%similar to>99.5%). (C) 2014 Elsevier Ltd. All rights reserved.
• Ni(II) Tol-BINAP-Catalyzed Enantioselective Michael Reactions of β-Ketoesters and Unsaturated <i>N</i>-Acylthiazolidinethiones
  作者：David A. Evans、Regan J. Thomson、Francisco Franco

  DOI：10.1021/ja053820q

  日期：2005.8.1

  The enantioselective addition of beta-ketoesters to unsaturated N-acylthiazolidinethiones catalyzed by Ni(II) Tol-BINAP Lewis acid complexes is reported. Notable features of this reaction are its operation simplicity, the obviated need for the addition of an external base, and the ease with which the adducts are converted into a range of potentially useful derivatives. In particular, the dihydropyrone adducts are versatile scaffolds for further stereoselective elaboration.
• Highly Enantioselective Catalytic Thiolysis of Prochiral Cyclic Dicarboxylic Anhydrides Utilizing a Bifunctional Chiral Sulfonamide
  作者：Takashi Honjo、Shigeki Sano、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.1002/anie.200501408

  日期：2005.9.12
• N-Heterocyclic Carbene Catalyzed CC Bond Cleavage in Redox Esterifications of Chiral Formylcyclopropanes
  作者：Stephanie S. Sohn、Jeffrey W. Bode

  DOI：10.1002/anie.200601919

  日期：2006.9.11