benzyl 2,3-dioxobutanoate | 93552-78-4

• 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: benzyl 2,3-dioxobutanoate
• 英文别名: benzyl 2,3-dioxobutyrate
• CAS: 93552-78-4
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: AFHZIVYYVKBHAB-UHFFFAOYSA-N

物化性质

• 沸点：
  327.1±35.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 2,3-dioxobutanoate 在 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.0h， 生成 benzyl (αS,6S,7S)-7-(1-acetoxyethyl)-3-methyl-2-isoxacephem-4-carboxylate
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure 2-Isoxacephems

  摘要：

  (alphaR,6R,7R)-7-(1-Acetoxyethyl)-3-methyl-2-isoxacephem-4-carboxylic acid and its enantiomer have been prepared. The ring systems were formed from the corresponding enantiomerically pure N-unsubstituted beta-lactams. The reduction of methyl [(alphaR,2S,3R)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate] has been solved via a hemi-acetal. The structure and the configuration of a new stereogenic center in this intermediate was predicted by using 2D NMR technique and unambiguously proven by x-ray.

  DOI：

  10.1007/s00706-003-0135-9
• 作为产物：
  描述：

  乙酰丙酮苄酯 在 BANT sensitizer 、 氧气 作用下， 以 氘代氯仿 为溶剂， 反应 26.0h， 生成 benzyl 2,3-dioxobutanoate
  参考文献：
  名称：

  单线态氧反应产生的邻位三羰基产物：在合成咔唑中的应用。

  摘要：

  通过使β-二羰基前体与DMF乙缩醛反应形成烯胺，可轻松形成邻三羰基体系，然后通过光氧化将其裂解。此过程可用于形成卡巴瑟姆。

  DOI：

  10.1016/0040-4039(84)80120-3

文献信息

• Vicinal Tricarbonyl products from singlet oxygen reactions.
  作者：Harry H. Wasserman、William T. Han

  DOI：10.1016/0040-4039(84)80120-3

  日期：1984.1

  Vicinal tricarbonyl systems are readily formed by reacting β-dicarbonyl precursors with DMF acetal to form enamines which are then cleaved by photooxidation. This procedure may be applied to the formation of carbacephams.

  通过使β-二羰基前体与DMF乙缩醛反应形成烯胺，可轻松形成邻三羰基体系，然后通过光氧化将其裂解。此过程可用于形成卡巴瑟姆。
• Displacement of Dinitrogen by Oxygen: A Methodology for the Catalytic Conversion of Diazocarbonyl Compounds to Ketocarbonyl Compounds by 2,6-Dichloropyridine-<i>N</i>-oxide
  作者：Yang Yu、Qiang Sha、Hui Cui、Kory S. Chandler、Michael P. Doyle

  DOI：10.1021/acs.orglett.7b03912

  日期：2018.2.2

  Dirhodium(II) catalyzed dinitrogen extrusion from diazocarbonyl compounds by 2,6-dichloropyridine-N-oxide forms ketocarbonyl compounds in near-quantitative yields. Reactions occur at room temperature, and the pyridine product does not coordinate with dirhodium(II) to inhibit catalysis. Anhydrous tricarbonyl compounds, as well as dicarbonyl compounds, are conveniently prepared by this methodology, and

  重氮（II）催化的重氮通过2,6-二氯吡啶-N-氧化物从重氮羰基化合物中挤出，以接近定量的产率形成酮羰基化合物。反应在室温下发生，并且吡啶产物不与二氢吡啶鎓（II）配位以抑制催化作用。通过这种方法可以方便地制备无水三羰基化合物以及二羰基化合物，并且它们已就地用于催化烯和羟醛的转化。
• Greff, Zoltan; Horvath, Zoltan; Nyitrai, Jozsef, Journal of Chemical Research, Miniprint, 1990, # 6, p. 1201 - 1258
  作者：Greff, Zoltan、Horvath, Zoltan、Nyitrai, Jozsef、Kajtar-Peredy, Maria、Brlik, Janos

  DOI：——

  日期：——
• Synthesis of thienamycin-like 2-iso-oxacephems with optional stereochemistry
  作者：Zsuzsanna Sánta、József Nagy、József Nyitrai

  DOI：10.1016/j.tetasy.2006.11.034

  日期：2006.11

  All four traps-stereoisomers of 7-(1-hydroxyethyl)-2-iso-oxacephem-4-carboxylic acids, which are the 2-iso-oxacephem analogues of Thienamycin, have been synthesized. (alpha R,6R,7R)- and (alpha S,6S,7S)-7-(1-hydroxyethyl)-3-methyl-2-iso-oxacephem-4-carboxylic acids have been prepared starting from L- and D-threonine, the configuration at the a-position was inverted by using Mitsunobu reactions providing the (alpha S,6R,7R)- and (alpha R,6S,7S)-diastereomers of the compounds above. A synthetic route to the cis-annelated analogues was also worked out. (c) 2006 Elsevier Ltd. All rights reserved.
• Alkenyl tricarbonyl derivatives of α-amino acids as trielectrophiles. Formation of heterocyclic-substituted products
  作者：Harry H Wasserman、Yun Oliver Long、Rui Zhang、Jonathan Parr

  DOI：10.1016/s0040-4039(02)00548-8

  日期：2002.4

  Alkenyl tricarbonyl esters have been prepared by reaction of mono aldehydes of dibasic amino acids with tricarbonyl esters. These systems undergo reaction with diamines and other dinucleophiles by a combination of Michael addition and nucleophilic attack at the electrophilic central carbonyl to form pyrrole derivatives. These monoaldehydes may also be used to incorporate imidazole and furan residues into the amino acid starting materials. (C) 2002 Elsevier Science Ltd. All rights reserved.