2-羟基-4-氧代-2-(4-甲氧基苯基)戊酸甲酯 | 1018902-02-7

• 分子结构分类: 有机化合物
• 中文名称: 2-羟基-4-氧代-2-(4-甲氧基苯基)戊酸甲酯
• 英文名称: 2-hydroxy-4-oxo-2-(4-methoxylphenyl)pentanoic acid methyl ester
• 英文别名: (R)-methyl 2-hydroxy-2-(4-methoxyphenyl)-4-oxopentanoate；methyl (2R)-2-hydroxy-2-(4-methoxyphenyl)-4-oxopentanoate
• CAS: 1018902-02-7
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: LPRBZRUQDWJRFO-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 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：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-methoxyphenylglyoxylate methyl ester 、 丙酮 在 (1S,2S)-N,N'-bis[(S)-prolyl]-1,2-bis(1-methylpyridin-2-yl)ethane-1,2-diamine bis(triflate) bis(trifluoroacetate) 作用下， 以 neat (no solvent) 为溶剂， 反应 24.17h， 以95%的产率得到2-羟基-4-氧代-2-(4-甲氧基苯基)戊酸甲酯
  参考文献：
  名称：

  （1,2-二氨基乙烷-1,2-二基）双（N-甲基吡啶鎓）盐作为设计可循环使用的基于脯氨酰胺的有机催化剂的前瞻平台

  摘要：

  在酮-酮，酮-醛和醛-醛体系中，在纯净条件下开发了一种用于不对称交叉羟醛反应的新型高效且高度可回收的有机催化剂。该催化剂具有两个脯氨酰胺片段和一个C 2对称的（1,2-二氨基乙烷-1,2-二基）双（N-甲基吡啶鎓）基团。在超过830小时（25个循环）的工作时间内，该催化剂保持了高活性和出色的立体选择性。从头开始的理论研究解释了所设计的非对映异构有机催化剂的产物的绝对构型和不同的立体诱导水平。

  DOI：

  10.1021/acs.joc.5b01555

文献信息

• In Situ Formed Bifunctional Primary Amine-Imine Catalyst for Asymmetric Aldol Reactions of α-Keto Esters
  作者：Xi Zhu、Aijun Lin、Ling Fang、Wei Li、Chengjian Zhu、Yixiang Cheng

  DOI：10.1002/chem.201100200

  日期：2011.7.18

  In prime condition: The hydrolysis of a chiral diimine precursor can be carried out by a Brønsted acid to form an in situ primary amine–imine intermediate as a bifunctional primary aminocatalyst, which promoted direct asymmetric aldol reactions between α‐keto esters and ketones in high yields (up to 88 %) and with excellent enantioselectivities (see scheme; R1, R2, R4=alkyl; R3=aryl).

  在最佳条件下：手性二亚胺前体的水解可通过布朗斯台德酸进行，形成原位伯胺-亚胺中间体，作为双官能伯氨基催化剂，从而促进α-酮酯与酮之间的直接不对称醛醇缩合反应。产率（高达88％）并且具有优异的对映选择性（参见方案； R 1，R 2，R 4＝烷基； R 3＝芳基）。
• Facile preparation of optically pure diamines and their applications in asymmetric aldol reactions
  作者：Quan-Zhong Liu、Xue-Lian Wang、Shi-Wei Luo、Bao-Lei Zheng、Da-Bin Qin

  DOI：10.1016/j.tetlet.2008.10.085

  日期：2008.12

  A family of optically pure diamines with tertiary-primary amine motif has been synthesized from optically pure binaphthol and amino acids. The catalysts are highly tunable in structure and has demonstrated high efficiency in direct aldol reactions. Thus, a variety of aldehydes or methyl 2-oxoacetates reacted with acetone in the presence of 10 mol% of catalyst and 20 mol% TFA furnishing the desired, alcohols in up to 99% yield with excellent enantioselectivities (up to 96% ee). (C) 2008 Elsevier Ltd. All rights reserved.
• Asymmetric aldol reactions in ketone/ketone systems catalyzed by ionic liquid-supported C2-symmetrical organocatalyst
  作者：Sergei V. Kochetkov、Alexander S. Kucherenko、Sergei G. Zlotin

  DOI：10.1016/j.mencom.2015.05.002

  日期：2015.5

  Ionic liquid-supported (1,S,2S)- and (1R,2R)-1,2-bis[(S)-prolinamido]-1,2-diphenylethanes act as organocatalysts in asymmetric aldol reactions of acetone with a-keto esters or trifluoroacetophenone providing high yields and from moderate to high enantioselectivity. Recycling of the catalyst with a gradual decrease in conversion and ee values is possible.