ethyl 3,3-dibromopyruvate | 76179-25-4

• 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: ethyl 3,3-dibromopyruvate
• 英文别名: Ethyl 3,3-dibromo-2-oxopropanoate
• CAS: 76179-25-4
• 化学式: C₅H₆Br₂O₃
• 分子量: 273.909
• InChiKey: MNNLKNXLOUVIKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  ethyl 3,3-dibromopyruvate 在 重水 、 碳酸氢钠 作用下， 以100%的产率得到ethyl 3-deuterio-3,3-dibromopyruvate
  参考文献：
  名称：

  Synthesis of (E)- and (Z)-3-deuteriophosphoenolpyruvate

  摘要：

  DOI：

  10.1021/jo00289a063
• 作为产物：
  描述：

  3-溴丙酮酸乙酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 ethyl 3,3-dibromopyruvate
  参考文献：
  名称：

  Synthesis of (E)- and (Z)-[2-((Dimethoxyphosphinyl)oxy)-3-ethoxy-3-oxo-1-propenyl]bromobis(triphenylphosphine)palladium and the X-ray Crystal Structure Determination for the E-Isomer

  摘要：

  We report the preparation of (E)- and (Z)-[2-((dimethoxyphosphinyl)oxy)-3-ethoxy-3-oxo-1-propenyl]- bromobis(triphenylphosphine)palladium from the corresponding ethyl (E)- and(Z)-3-bromo-2[(dimethoxyphosphinyl)oxy]propenoate and the X-ray crystal structure determination for (E)-[2-((dimethoxyphosphinyl)oxy)-3-ethoxy-3-oxo- 1-propenyl]bromobis(triphenylphosphine)palladium. The (E)-palladium complex was reduced to (E)-3-[H-2]phosphoenolpyruvate by treatment with a mixture of trifluoroacetic acid-d/trifluoroacetic anhydride under strict anhydrous conditions. The H-1-NMR spectrum of the E-isomer obtained from the reduction of the palladium complex was identical to the H-1-NMR spectra of(E)-3-[H-2]phosphoenolpyruvate previously prepared by two different synthetic strategies. The X-ray structure of the palladium phosphoenolpyruvate analogue is the first X-ray structure of any 3-substituted phosphoenolpyruvate analogue reported and along with its synthesis and transformation interrelates the stereochemistry of several S-substituted phosphoenolpyruvate analogues.

  DOI：

  10.1021/jo00098a043

文献信息

• Optimization of imidazole amide derivatives as cannabinoid-1 receptor antagonists for the treatment of obesity
  作者：Roger A. Smith、Zahra Fathi、Furahi Achebe、Christiana Akuche、Su-Ellen Brown、Soongyu Choi、Jianmei Fan、Susan Jenkins、Harold C.E. Kluender、Anish Konkar、Rico Lavoie、Ronald Mays、Jennifer Natoli、Stephen J. O’Connor、Astrid A. Ortiz、Ning Su、Christy Taing、Susan Tomlinson、Theresa Tritto、Gan Wang、Stephan-Nicholas Wirtz、Wai Wong、Xiao-Fan Yang、Shihong Ying、Zhonghua Zhang

  DOI：10.1016/j.bmcl.2007.03.011

  日期：2007.5

  Several imidazole-based cyclohexyl amides were identified as potent CB-1 antagonists, but they exhibited poor oral exposure in rodents. Incorporation of a hydroxyl moiety on the cyclohexyl ring provided a dramatic improvement in oral exposure, together with a ca. 10-fold decrease in potency. Further optimization provided the imidazole 2-hydroxy-cyclohexyl amide 45, which exhibited hCB-1 K-i = 3.7 nM and caused significant appetite suppression and robust, dose-dependent reduction of body weight gain in industry-standard rat models. (c) 2007 Elsevier Ltd. All rights reserved.
• GORE, MAKARAND P.;NANJAPPAN, PALANIAPPAGOWNDER;HOOPS, GEOFFREY C.;WOODARD+, J. ORG. CHEM., 55,(1990) N, C. 758-760
  作者：GORE, MAKARAND P.、NANJAPPAN, PALANIAPPAGOWNDER、HOOPS, GEOFFREY C.、WOODARD+

  DOI：——

  日期：——
• Synthesis of (E)- and (Z)-[2-((Dimethoxyphosphinyl)oxy)-3-ethoxy-3-oxo-1-propenyl]bromobis(triphenylphosphine)palladium and the X-ray Crystal Structure Determination for the E-Isomer
  作者：Garry D. Dotson、Jeffrey W. Kampf、Ronald W. Woodard

  DOI：10.1021/jo00098a043

  日期：1994.9

  We report the preparation of (E)- and (Z)-[2-((dimethoxyphosphinyl)oxy)-3-ethoxy-3-oxo-1-propenyl]- bromobis(triphenylphosphine)palladium from the corresponding ethyl (E)- and(Z)-3-bromo-2[(dimethoxyphosphinyl)oxy]propenoate and the X-ray crystal structure determination for (E)-[2-((dimethoxyphosphinyl)oxy)-3-ethoxy-3-oxo- 1-propenyl]bromobis(triphenylphosphine)palladium. The (E)-palladium complex was reduced to (E)-3-[H-2]phosphoenolpyruvate by treatment with a mixture of trifluoroacetic acid-d/trifluoroacetic anhydride under strict anhydrous conditions. The H-1-NMR spectrum of the E-isomer obtained from the reduction of the palladium complex was identical to the H-1-NMR spectra of(E)-3-[H-2]phosphoenolpyruvate previously prepared by two different synthetic strategies. The X-ray structure of the palladium phosphoenolpyruvate analogue is the first X-ray structure of any 3-substituted phosphoenolpyruvate analogue reported and along with its synthesis and transformation interrelates the stereochemistry of several S-substituted phosphoenolpyruvate analogues.
• 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.
• Synthesis of (E)- and (Z)-3-deuteriophosphoenolpyruvate
  作者：Makarand P. Gore、Palaniappagownder Nanjappan、Geoffrey C. Hoops、Ronald W. Woodard

  DOI：10.1021/jo00289a063

  日期：1990.1