2-(4-bromophenyl)-2-oxoethyl 2-methylbutanoate | 100713-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-bromophenyl)-2-oxoethyl 2-methylbutanoate
• 英文别名: [2-(4-bromophenyl)-2-oxoethyl] 2-methylbutanoate
• CAS: 100713-31-3
• 化学式: C₁₃H₁₅BrO₃
• 分子量: 299.164
• InChiKey: DWEPOSPZDCKWMK-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C(Solv: water (7732-18-5); methanol (67-56-1))
• 沸点：
  371.9±22.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 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：

  2-甲基丁酸 、 2,4'-二溴苯乙酮 在 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-(4-bromophenyl)-2-oxoethyl 2-methylbutanoate
  参考文献：
  名称：

  Varitatin A, a Highly Modified Fatty Acid Amide from Penicillium variabile Cultured with a DNA Methyltransferase Inhibitor

  摘要：

  A new, highly modified fatty acid amide, varitatin A (1), was isolated from the fungus Penicillium variabile HXQ-H-1 cultivated with the DNA methyltransferase inhibitor 5-azacytidine. The structure including the absolute configuration of 1 was established by analysis of NMR and MS data, together with chemical degradation and Mosher's method based on MPA esters. Compound 1 showed cytotoxicity against HCT-116 cells with an IC50 value of 2.8 mu M and also inhibited the effects of protein tyrosine kinases.

  DOI：

  10.1021/acs.jnatprod.5b00742

文献信息

• Biocatalytic Construction of Quaternary Centers by Aldol Addition of 3,3-Disubstituted 2-Oxoacid Derivatives to Aldehydes
  作者：Roser Marín-Valls、Karel Hernández、Michael Bolte、Teodor Parella、Jesús Joglar、Jordi Bujons、Pere Clapés

  DOI：10.1021/jacs.0c09994

  日期：2020.11.18

  3-methyl-2-oxobutanoate hydroxymethyltransferase from E. coli (KPHMT) and variants thereof. The 3,3,3-trisubstituted 2-oxoacids thus produced were converted into 2-oxolactones and 3-hydroxy acids and directly to ulosonic acid derivatives, all bearing gem-dialkyl, gem-cycloalkyl, and spirocyclic quaternary centers. In addition, some of these reactions use a single enantiomer from racemic nucleophiles to afford

  季碳的拥挤性质阻碍了它们的制备，尤其是在需要立体控制时。在这里，我们报告了一种用于创建具有广泛底物范围的季碳中心的生物催化方法，导致具有这种结构特征的不同化合物类别。关键步骤包括由来自大肠杆菌的金属依赖性 3-甲基-2-氧代丁酸羟甲基转移酶 (KPHMT) 及其变体催化，将 3,3-二取代的 2-含氧酸醛醇加成到醛上。由此产生的 3,3,3-三取代的 2-含氧酸被转化为 2-氧代内酯和 3-羟基酸，并直接转化为 ulosonic 酸衍生物，所有这些衍生物都带有嵴二烷基、嵴环烷基和螺环季铵中心。此外，这些反应中的一些使用来自外消旋亲核试剂的单一对映异构体来提供立体纯的季碳。
• Varitatin A, a Highly Modified Fatty Acid Amide from <i>Penicillium variabile</i> Cultured with a DNA Methyltransferase Inhibitor
  作者：Xueqian He、Zhenzhen Zhang、Yinghan Chen、Qian Che、Tianjiao Zhu、Qianqun Gu、Dehai Li

  DOI：10.1021/acs.jnatprod.5b00742

  日期：2015.11.25

  A new, highly modified fatty acid amide, varitatin A (1), was isolated from the fungus Penicillium variabile HXQ-H-1 cultivated with the DNA methyltransferase inhibitor 5-azacytidine. The structure including the absolute configuration of 1 was established by analysis of NMR and MS data, together with chemical degradation and Mosher's method based on MPA esters. Compound 1 showed cytotoxicity against HCT-116 cells with an IC50 value of 2.8 mu M and also inhibited the effects of protein tyrosine kinases.