phenylmethyl 3-methyl-2-oxobutanoate | 76585-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenylmethyl 3-methyl-2-oxobutanoate
• 英文别名: benzyl 3-methyl-2-oxobutanoate；3-Methyl-2-oxo-butyric acid benzyl ester；benzyl 3-methyl-2-ketobutyrate
• CAS: 76585-78-9
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: KKLBVJNMBJECIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenylmethyl 3-methyl-2-oxobutanoate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三乙胺 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 4.17h， 生成 phenylmethyl (2S,5Z)-2-(1-methylethyl)-4-oxo-5-(phenylmethylene)-1,3-dioxolane-2-carboxylate
  参考文献：
  名称：

  Guignardic Acid, a Novel Type of Secondary Metabolite Produced by the Endophytic FungusGuignardia sp.: Isolation, Structure Elucidation, and Asymmetric Synthesis

  摘要：

  A UV-guided fractionation of the AcOEt extract of the fermentation broth of Guignardia sp., an endophytic fungus from the leaves of the tropical tree Spondias mombin, resulted in the identification of the new metabolite (-)-(2S,5Z)-2-(1-methylethyl)-4-oxo-5-(phenylmethylene)-1,3-dioxolane-2-carboxylic acid (1), isolated as NHT4+ salt 1a. The metabolite 1 was designated (-)-(S)-guignardic acid. This first member of a new class of natural compounds contains a dioxolanone moiety formed by fusion of 2-oxo-3-phenylpropanoic acid (phenylpyruvic acid) and 3-methyl-2-oxobutanoic acid (dimethylpyruvic acid), products of the oxidative deamination of phenylalanine and valine. respectively. The structure of 1a was deduced from spectral data (UV. IR, MS. H-1- and C-13-NMR) and confirmed by asymmetric synthesis.

  DOI：

  10.1002/1522-2675(20011219)84:12<3766::aid-hlca3766>3.0.co;2-z
• 作为产物：
  描述：

  sodium 3-methyl-2-oxobutyrate 、 苯甲醇 在 氯化亚砜 作用下， 反应 0.5h， 以82%的产率得到phenylmethyl 3-methyl-2-oxobutanoate
  参考文献：
  名称：

  Guignardic Acid, a Novel Type of Secondary Metabolite Produced by the Endophytic FungusGuignardia sp.: Isolation, Structure Elucidation, and Asymmetric Synthesis

  摘要：

  A UV-guided fractionation of the AcOEt extract of the fermentation broth of Guignardia sp., an endophytic fungus from the leaves of the tropical tree Spondias mombin, resulted in the identification of the new metabolite (-)-(2S,5Z)-2-(1-methylethyl)-4-oxo-5-(phenylmethylene)-1,3-dioxolane-2-carboxylic acid (1), isolated as NHT4+ salt 1a. The metabolite 1 was designated (-)-(S)-guignardic acid. This first member of a new class of natural compounds contains a dioxolanone moiety formed by fusion of 2-oxo-3-phenylpropanoic acid (phenylpyruvic acid) and 3-methyl-2-oxobutanoic acid (dimethylpyruvic acid), products of the oxidative deamination of phenylalanine and valine. respectively. The structure of 1a was deduced from spectral data (UV. IR, MS. H-1- and C-13-NMR) and confirmed by asymmetric synthesis.

  DOI：

  10.1002/1522-2675(20011219)84:12<3766::aid-hlca3766>3.0.co;2-z

文献信息

• Novel imidazoles
  申请人：Bolton Louis Gary

  公开号：US20050239857A1

  公开（公告）日：2005-10-27

  Novel imidazoles are provided. The compounds are useful as HMGCo-A Reductase Inhibitor. Also provided are pharmaceutical compositions of the compounds. Methods of making and methods of using the compounds are also provided.

  提供了新型咪唑类化合物。这些化合物可用作HMGCo-A还原酶抑制剂。还提供了这些化合物的药物组合物。还提供了制备这些化合物的方法和使用这些化合物的方法。
• Metallo-beta-lactamase inhibitors
  申请人：Chikauchi Ken

  公开号：US20080090825A1

  公开（公告）日：2008-04-17

  A new metallo-β-lactamase inhibitor which acts as a medicament for inhibiting the inactivation of β-lactam antibiotics and recovering anti-bacterial activities is disclosed. The maleic acid derivatives having the general formula (I) have metallo-β-lactamase inhibiting activities. It is possible to recover the anti-bacterial activities of β-lactam antibiotics against metallo-β-lactamase producing bacteria by combining the compound of the general formula (I) with β-lactam antibiotics.

  一种新的金属β-内酰胺酶抑制剂，作为一种药物用于抑制β-内酰胺类抗生素的失活并恢复抗菌活性。具有一般式（I）的马来酸衍生物具有金属β-内酰胺酶抑制活性。通过将一般式（I）的化合物与β-内酰胺类抗生素结合，可以恢复β-内酰胺酶产生细菌对β-内酰胺类抗生素的抗菌活性。
• [EN] PROCESS FOR PRODUCING CARBOXYLIC ACID ESTER<br/>[FR] PROCÉDÉ DE PRODUCTION D'UN ESTER D'ACIDE CARBOXYLIQUE
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2012176930A1

  公开（公告）日：2012-12-27

  An object of the present invention is to provide a new process which can produce a carboxylic acid ester from an aldehyde. The object is achieved by a process for producing a carboxylic acid ester, including the step of mixing a compound represented by the formula (2-1): (wherein R2 represents an alkyl group optionally having a substituent, or the like; R3 and R4 each represent independently an alkyl group optionally having a substituent, or the like, or R3 and R4 are taken together to form a divalent hydrocarbon group optionally having a substituent, or the like; Y represents a group represented by -S- or a group represented by -N(R5)-; R5 represents an alkyl group optionally having a substituent, or the like, or R5 is taken together with R4 to form a divalent hydrocarbon group optionally having a substituent; and X- represents an anion), a base, an alcohol, oxygen and an aldehyde to oxidize the aldehyde.

  本发明的一个目的是提供一种新的过程，可以从醛中产生羧酸酯。该目的通过一种生产羧酸酯的过程实现，包括混合以下公式表示的化合物（2-1）的步骤：（其中R2代表一个烷基基团，可选地具有取代基，或类似物；R3和R4分别独立地代表一个烷基基团，可选地具有取代基，或类似物，或者R3和R4结合在一起形成一个二价碳氢基团，可选地具有取代基，或类似物；Y代表一个由-S-表示的基团或由-N(R5)-表示的基团；R5代表一个烷基基团，可选地具有取代基，或类似物，或R5与R4结合在一起形成一个二价碳氢基团，可选地具有取代基；X-代表一个阴离子），一种碱，一种醇，氧气和一种醛来氧化该醛。
• Chiral 2,6-Bis(oxazolinyl)pyridine−Rare Earth Metal Complexes as Catalysts for Highly Enantioselective 1,3-Dipolar Cycloaddition Reactions of 2-Benzopyrylium-4-olates
  作者：Hiroyuki Suga、Kei Inoue、Shuichi Inoue、Akikazu Kakehi、Motoo Shiro

  DOI：10.1021/jo049007f

  日期：2005.1.1

  enantioselectivity were obtained in 1,3-dipolar cycloadditions of 2-benzopyrylium-4-olate generated from the Rh2(OAc)4-catalyzed decomposition of o-methoxycarbonyl-α-diazoacetophenone. This reaction utilized chiral 2,6-bis(oxazolinyl)pyridine (Pybox)−rare earth metal triflate complexes as chiral Lewis acid catalysts. The reactions with several benzyloxyacetaldehyde derivatives catalyzed by a Sc(III)−Pybox-i-Pr

  从Rh 2（OAc）4催化的邻甲氧基羰基-α-二重氮苯乙酮的分解反应生成的2-苯并吡啶-4-醇酸酯的1，3-偶极环加成反应中，获得了显着水平的对映选择性。该反应利用手性2，6-双（恶唑啉基）吡啶（Pybox）-稀土金属三氟甲磺酸盐配合物作为手性路易斯酸催化剂。由Sc（III）-Pybox- i- Pr配合物（10 mol％）催化的几种苄氧基乙醛衍生物的反应顺利进行，以高对映选择性（至多93％ee）选择性地产生内加合物。对于与丙酮酸苄酯的反应，Sc（III）-Pybox- i-Pr复合物（10摩尔％）的三氟乙酸（10摩尔％）的存在下有效地催化的反应，得到外-adduct同时具有高diastereo-和对映选择性（94％ee）的。该催化体系可有效地用于与其他几种具有高外向和对映选择性（高达95％ee）的α-酮酸酯的反应。与用羰基化合物的反应，镱（III）-Pybox-PH复合物（10摩尔％）被
• [EN] PROCESS FOR PRODUCING CARBOXYLIC ACID ESTER<br/>[FR] PROCÉDÉ DE PRODUCTION D'ESTER D'ACIDE CARBOXYLIQUE
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2012026617A1

  公开（公告）日：2012-03-01

  The present invention relates to a process for producing a carboxylic acid ester, comprising a step of oxidizing an aldehyde by mixing an alcohol, carbon dioxide, the aldehyde and at least one compound selected from the group consisting of compounds represented by the formulae (2-1) and (2-2): wherein R2 represents an alkyl group optionally having a substituent or the like; R3 and R4 each independently represents an alkyl group optionally having a substituent or the like or R3 and R4 are linked together to form a divalent hydrocarbon group optionally having a substituent or the like; Y represents a group of -S- or a group of -N(R5)-, wherein R5 represents an alkyl group optionally having a substituent or the like, or R5 is linked to R4 to form a divalent hydrocarbon group optionally having a substituent; and R8 represents an alkyl group.

  本发明涉及一种生产羧酸酯的方法，包括通过混合醇、二氧化碳、醛和来自由式（2-1）和（2-2）所代表的化合物组成的群体中至少选取一种化合物，氧化醛的步骤：其中R2代表可能具有取代基等的烷基基团；R3和R4各自独立地代表可能具有取代基等的烷基基团，或者R3和R4连接在一起形成可能具有取代基等的二价碳氢基团；Y代表一个-S-基团或一个-N(R5)-基团，其中R5代表可能具有取代基等的烷基基团，或者R5连接到R4形成可能具有取代基的二价碳氢基团；R8代表一个烷基基团。