4-(2-甲氧基苯基)-4-氧代丁酸甲酯 | 99046-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-(2-甲氧基苯基)-4-氧代丁酸甲酯
• 英文名称: 4-oxo-4-(2-methoxyphenyl)butyric acid methyl ester
• 英文别名: methyl 4-(2-methoxyphenyl)-4-oxobutanoate；4-(2-methoxy-phenyl)-4-oxo-butyric acid methyl ester；4-(2-Methoxy-phenyl)-4-oxo-buttersaeure-methylester
• CAS: 99046-13-6
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: SQUAOXHPCJIDJM-UHFFFAOYSA-N

物化性质

• 沸点：
  160 °C(Press: 3 Torr)
• 密度：
  1.168 g/cm3(Temp: 27.5 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  F,Xi
• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  4-(2-甲氧基苯基)-4-氧代丁酸甲酯 在 sodium hydroxide 、 二异丁基氢化铝 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 生成 trans-(RS,SR)-γ-hydroxy-β-methoxy-γ-phenylbutanoic acid lactone
  参考文献：
  名称：

  Stereoselective reduction of .gamma.-oxobutanoic acids using DIBAL-H and zinc chloride

  摘要：

  A variety of gamma-aromatic gamma-ketobutanoic acids can be reduced selectively, under optimized conditions, by the use of DIBAL-H and ZnCl2 to provide the (RS,SR)-gamma-aryl-gamma-hydroxy-beta-methylbutanoic acids. Further evidence has been gathered to support the hypothesis that the reaction proceeds by formation of a seven-membered ring complex with the aluminium or zinc atom bridging the ketone and carboxyl groups which preceeds the reduction step and that this templated reduction accounts for observed high diastereoselectivity. Also we have shown that some gamma-aryl-gamma-butyrolactones can be easily transformed via an oxidative cleavage of the aromatic ring to provide selective synthesis of either cis- or trans-tetrahydro-3-methyl-5-oxo-2-furancarboxylic acid derivatives.

  DOI：

  10.1021/jo00009a030
• 作为产物：
  描述：

  3-(2-羟基苯甲酰基)丙酸 在 甲醇 、 sodium hydroxide 、 mineral acid 作用下， 生成 4-(2-甲氧基苯基)-4-氧代丁酸甲酯
  参考文献：
  名称：

  Trivedi; Nargund, Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1941, vol. 10/3A, p. 99

  摘要：

  DOI：

文献信息

• Mg(OMe)₂ promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters
  作者：Luhao Lai、A-Ni Li、Jiawei Zhou、Yarong Guo、Li Lin、Wei Chen、Rui Wang

  DOI：10.1039/c7ob00131b

  日期：——

  This work concerns the Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters with TMEDA as an additive. The isomerization proceeded under mild conditions and afforded γ-keto esters in high yield (up to 96%) within 2 h. Both (Z)- and (E)-γ-hydroxy-α,β-alkenoic esters were tolerated under the reaction conditions. This transformation involves the in situ formation of a dienolate intermediate

  这项工作涉及以TMEDA作为添加剂的Mg（OMe）2促进的γ-羟基-α，β-链烯酸酯的烯丙基异构化。异构化在温和的条件下进行，并在2小时内以高收率（高达96％）提供了γ-酮酯。在反应条件下，（Z）-和（E）-γ-羟基-α，β-链烯酸酯均被耐受。该转化涉及从容易获得的γ-羟基-α，β-链烯酸酯原位形成二烯酸酯中间体。该原位生成的二烯醇酯可以与苯甲醛反应并经历一种实用，有用的串联烯丙基异构化-羟醛反应，得到更多官能的化合物。
• Copper-catalyzed cascade reactions of α,β-unsaturated esters with keto esters
  作者：Zhengning Li、Chongnian Wang、Zengchang Li

  DOI：10.3762/bjoc.11.23

  日期：——

  A copper-catalyzed cascade reaction of alpha,beta-unsaturated esters with keto esters is reported. It features a copper-catalyzed reductive aldolization followed by a lactonization. This method provides a facile approach to prepare gamma-carboxymethyl-gamma-lactones and delta-carboxymethyl-delta-lactones under mild reaction conditions.

  据报道，铜催化的α，β-不饱和酯与酮酯的级联反应。其特征在于铜催化的还原性醛醇缩合，然后是内酯化。该方法提供了在温和的反应条件下制备γ-羧甲基-γ-内酯和δ-羧甲基-δ-内酯的简便方法。
• γ-烃氧酰基甲基-γ-丁内酯、δ-烃氧酰基甲 基-δ-戊内酯的合成方法
  申请人：大连大学

  公开号：CN104250236B

  公开（公告）日：2017-03-01

  本发明属于化工技术领域，具体涉及一种γ‑烃氧酰基甲基‑γ‑丁内酯、δ‑烃氧酰基甲基‑δ‑戊内酯的合成方法。以CuH化合物为还原剂、与酮酸酯、α,β‑不饱和羧酸酯反应；以CuH化合物为催化剂，酮酸酯、α,β‑不饱和羧酸酯、硅氢化合物或硼氢化合物间反应；由其它铜化合物、膦配体、硅氢化合物或硼氢化合物反应生成催化剂，直接催化硅氢化合物或硼氢化合物与酮酸酯、α,β‑不饱和羧酸酯的反应这三种方法进行合成反应。本发明方法通过串联反应合成，在同一反应容器中连续进行三步反应，不需要分离中间产物、避免了中间分离过程和由此造成的损失，操作简便，提高反应效率，具有良好的应用价值。
• Design and synthesis of 4-aryl-4-oxobutanoic acid amides as calpain inhibitors
  作者：Yong Zhang、Seo Yoon Jung、Changbae Jin、Nam Doo Kim、Ping Gong、Yong Sup Lee

  DOI：10.1016/j.bmcl.2008.11.030

  日期：2009.1

  The involvement of mu-calpain in neurological disorders, such as stroke and Alzheimer's disease has attracted considerable interest in the use of calpain inhibitors as therapeutic agents. 4-Aryl-4-oxobutanoic acid amide derivatives 4 were designed as acyclic variants of mu-calpain inhibitory chromone and quinolinone derivatives. Of the compounds synthesized, 4c-2, which possesses a 2-methoxymethoxy group at the phenyl ring and a primary amide at the warhead region most potently inhibited mu-calpain (IC50 = 0.34 mu M). Our findings suggest that the 4-aryl-4-oxobutanoic acid amide derivatives should be considered as a new family of mu-calpain inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.
• Baddar et al., Journal of the Chemical Society, 1955, p. 461,464
  作者：Baddar et al.

  DOI：——

  日期：——