Diethyl 2-bromo-2-fluoro-3-oxobutanedioate | 2707-82-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: Diethyl 2-bromo-2-fluoro-3-oxobutanedioate
• 英文别名: diethylbromofluorooxaloacetate；Fluor-brom-aethoxalyl-essigsaeure-aethylester；Brom-fluor-oxalessigsaeure-diethylester；Bromfluoroxalessigsaeurediethylester
• CAS: 2707-82-6
• 化学式: C₈H₁₀BrFO₅
• 分子量: 285.067
• InChiKey: QCXOQJVDTYDTCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Diethyl 2-bromo-2-fluoro-3-oxobutanedioate 在 sodium ethanolate 作用下， 以 乙醚 、 苯 为溶剂， 生成 2,4-Difluor-2-aethoxalyl-acetessigsaeure-aethylester
  参考文献：
  名称：

  648.有机氟化合物。第十六部分。乙草酰氟乙酸乙酯的制备与反应

  摘要：

  DOI：

  10.1039/jr9600003225
• 作为产物：
  描述：

  2-氟-3-氧-丁酸-1,4-二乙酯 在 溴 作用下， 以 苯 为溶剂， 生成 Diethyl 2-bromo-2-fluoro-3-oxobutanedioate
  参考文献：
  名称：

  648.有机氟化合物。第十六部分。乙草酰氟乙酸乙酯的制备与反应

  摘要：

  DOI：

  10.1039/jr9600003225
• 作为试剂：
  描述：

  丙二酸二乙酯 在 Diethyl 2-bromo-2-fluoro-3-oxobutanedioate 作用下， 以 苯 为溶剂， 生成 溴代丙二酸二乙酯
  参考文献：
  名称：

  648.有机氟化合物。第十六部分。乙草酰氟乙酸乙酯的制备与反应

  摘要：

  DOI：

  10.1039/jr9600003225

文献信息

• A Convenient Synthesis of Ethyl (Diethoxyphosphoryl) fluoroacetate from Ethyl Fluoroacetate
  作者：Elias Elkik、Michèle Imbeaux

  DOI：10.1055/s-1989-27412

  日期：——

  A new synthesis of ethyl (diethoxyphosphoryl)fluoroacetate starting from ethyl fluoroacetate is described for a mole scale. This synthesis does not require the use of special equipment for fluorine chemistry since no hydrogen fluoride is evolved.

  以氟乙酸乙酯为起始原料，以摩尔为尺度，描述了一种新的乙基（二乙氧基磷酰）氟乙酸酯合成方法。由于不产生氟化氢，该合成方法不需要使用氟化学的特殊设备。
• Ife,R.J. et al., Journal of the Chemical Society. Perkin transactions I, 1976, p. 1776 - 1783
  作者：Ife,R.J. et al.

  DOI：——

  日期：——
• Bergmann,E.D.; Shahak,I., Journal of the Chemical Society, 1960, p. 462 - 463
  作者：Bergmann,E.D.、Shahak,I.

  DOI：——

  日期：——
• Probing the Stereochemistry of <i>E. coli</i> 3-Deoxy-<scp>d</scp>-<i>arabino</i>-heptulosonate 7-Phosphate Synthase (Phenylalanine-Sensitive)-Catalyzed Synthesis of KDO 8-P Analogues
  作者：Appavu K. Sundaram、Ronald W. Woodard

  DOI：10.1021/jo991529l

  日期：2000.9.1

  The five-carbon phosphorylated monosaccharide analogues, D-arabinose 5-phosphate, D-ribose B-phosphate, and 2-deoxy-D-ribose 5-phosphate, were separately condensed with (Z)- and (E)-[3-H-2]-phosphoenolpyruvate (PEP) in the presence of Escherichia coli 3-deoxy-D-arabino-heptulosonate 7-phosphate (DAH 7-P) synthase (phe) to give in the case of (Z)-[3-H-2]-PEP (3S)-[3-H-2]-3-deoxy-D-manno-octulosonate S-phosphate, (3S)-[3-H-2]-3-deoxy-D-altro-octulosonate 8-phosphate, and (3S)-[3-H-2]-3,5-dideoxy-D-altro-octulosonate 8-phosphate, respectively, whereas incubation with (E)-[3(2)H]-PEP gives the corresponding (3R)-monosaccharides. These results are in complete agreement with the observed facial selectivity of DAH 7-P synthase for its normal substrates D-erythrose 4-phosphate and PEP and provide direct evidence that DAH 7-P synthase (phe) catalyzes the si face addition of the C3 of PEP to the re face of C1 of the phosphorylated monosaccharides tested. Products formed by DAH 7-P synthase (phe)-catalyzed condensation of(Z)- and (E)-[3-F]-PEP with E 4-P were completely characterized by H-1 and F-19 NMR analysis for the first time. Results of our studies suggest that disappearence of the double bond between C2 and C3 of PEP and formation of a bond between C3 of PEP and C1 of the phosphorylated monosaccharide tested occur in concert during the DAH 7-P synthase-catalyzed condensation reaction.
• ELKIK, ELIAS;IMBEAUX, MICHELE, SYNTHESIS,(1989) N1, C. 862-864
  作者：ELKIK, ELIAS、IMBEAUX, MICHELE

  DOI：——

  日期：——