<2-13C>ethyl acetoacetate | 77504-78-0

• 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: <2-13C>ethyl acetoacetate
• 英文别名: ethyl <2-13C>acetoacetate；ethyl [2-¹³C]acetoacetate；[2-13C]ethyl acetoacetate；ethyl 3-oxo(213C)butanoate
• CAS: 77504-78-0
• 化学式: C₆H₁₀O₃
• 分子量: 131.133
• InChiKey: XYIBRDXRRQCHLP-AZXPZELESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  9.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  吡喃-4-酮 、 <2-13C>ethyl acetoacetate 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 15.33h， 以87%的产率得到ethyl 4-hydroxy[1-¹³C]benzoate
  参考文献：
  名称：

  4-HYDROXY[1-13C]BENZOIC ACID

  摘要：

  DOI：

  10.15227/orgsyn.078.0113
• 作为产物：
  描述：

  乙酸乙酯-2-13C 、 乙酰氯 在 正丁基锂 、 六甲基二硅氮烷 作用下， 生成 <2-13C>ethyl acetoacetate
  参考文献：
  名称：

  Late intermediates in the biosynthesis of cocaine: 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate and methyl ecgonine

  摘要：

  Methyl (RS)-[1,2-C-13(2),1-C-14]-4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate was synthesized from a mixture of sodium [1,2-C-13(2)]- and (1-C-14]acetate. This beta-keto ester was administered to intact Erythroxylum coca plants, resulting in the formation of labeled cocaine and methyl ecgonine. The presence of contiguous C-13 atoms in these alkaloids at C-2 and C-9 was established by C-13 NMR spectroscopy, and the presence of C-14 at C-9 was established by a chemical degradation. These results are consistent with our new hypothesis for the biosynthesis of cocaine, which involves the intermediacy of 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate (rather than 2-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate) in the formation of the tropane moiety of cocaine. Support for this biogenetic scheme was also obtained by a biomimetic synthesis of 2-carbomethoxy-3-tropinone by the oxidation of methyl 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate with mercuric acetate. The formation of labeled cocaine and methyl ecgonine in leaf cuttings of Erythroxylum coca was observed after incubation with. [9-C-14]-2-carbomethoxy-3-tropinone. The degree of incorporation of this precursor into cocaine was significantly increased by the concomitant administration of the N-acetylcysteamine thioester of benzoic acid, with a corresponding reduction in the degree of incorporation into methyl ecgonine.

  DOI：

  10.1021/ja00024a039

文献信息

• Townsend, Craig A.; Christensen, Siegfried B.; Davis, Steven G., Journal of the Chemical Society. Perkin transactions I, 1988, p. 839 - 862
  作者：Townsend, Craig A.、Christensen, Siegfried B.、Davis, Steven G.

  DOI：——

  日期：——
• Bisfuran formation in aflatoxin biosynthesis: the fate of the averufin side chain
  作者：Craig A. Townsend、Siegfried B. Christensen、Steven G. Davis

  DOI：10.1021/ja00386a069

  日期：1982.11
• DALESSANDRO G.; SLEITER G., J. LABELLED COMPOUNDS AND RADIOPHARM., 1980, 17, NO 6, 813-824
  作者：DALESSANDRO G.、 SLEITER G.

  DOI：——

  日期：——