<1-13C>Malonsaeure-diethylester | 79341-48-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: <1-13C>Malonsaeure-diethylester
• 英文别名: diethyl <3-13C>methylmalonate；diethyl malonate-<1-13C>；diethyl [carbonyl-13C1]malonate；diethyl malonate-1-13C；[1-¹³C]malonic acid diethyl ester；diethyl (113C)propanedioate
• CAS: 79341-48-3
• 化学式: C₇H₁₂O₄
• 分子量: 161.159
• InChiKey: IYXGSMUGOJNHAZ-PTQBSOBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <1-13C>Malonsaeure-diethylester 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Solution conformations of barbituric acid derivatives: a 3J(13C,1H) NMR study

  摘要：

  The conformations of the 5-alkyl chains of 5,5-dialkylbarbituric acid derivatives in polar and nonpolar media were determined from the magnitudes of the vicinal heteronuclear coupling constants between the alpha-alkyl hydrogens and the carbonyl carbons. The experimental 3J values have been compared to theoretical values, and the conformational populations of the alkyl side chains with respect to the trioxopyrimidine ring have been determined. The results show that all these compounds have a very low barrier to rotation for both butyl and ethyl side chains. The barbiturates that do not have a 1'-methyl group in the butyl side chain, butobarbital and amobarbital, have no preferred conformation for either the butyl or ethyl side chains. However, the compounds with a 1'-methyl group, pentobarbital and alpha-methylamobarbital, exhibit preferred conformation for both alkyl chains. The significance of these results to the relationship between conformations and pharmacological activity is discussed.

  DOI：

  10.1021/jm00375a019
• 作为产物：
  描述：

  乙醇 、 <1-13C>-propanedioic acid 在 硫酸 作用下， 生成 <1-13C>Malonsaeure-diethylester
  参考文献：
  名称：

  A mechanistic study on the amination of 2-chloro-3,5-dinitropyridine with liquid ammonia

  摘要：

  DOI：

  10.1021/jo00366a027

文献信息

• Synthesis of diethyl [carbonyl-11C]malonate from [11C]carbon monoxide by rhodium-promoted carbonylation and its application as a reaction intermediate
  作者：Julien Barletta、Farhad Karimi、Hisashi Doi、Bengt Långström

  DOI：10.1002/jlcr.1098

  日期：2006.8

  Rhodium-mediated carbonylation reaction was applied to synthesize diethyl [carbonyl-C-11]malonate using [C-11]carbon monoxide at low concentration. The synthesis was performed starting with ethyl d ...

  使用低浓度的[C-11]一氧化碳，应用铑介导的羰基化反应合成[羰基-C-11]丙二酸二乙酯。合成是从乙基d开始进行的...
• The Biosynthesis of Monensin-A: Thymine, .BETA.-Aminoisobutyrate and Methacrylate Metabolism in Streptomyces cinnamonensis.
  作者：DAVID O''HAGAN、SARAH V. ROGERS、GORDON R. DUFFIN、KEVIN A. REYNOLDS

  DOI：10.7164/antibiotics.48.1280

  日期：——

  Feeding experiments with isotopically labelled samples of [13C, 2H3-methyl]-thymine, (R, S)-[1-13C]- and (R, S)-[13C-methyl]-β-aminoisobutyrates into monensin-A demonstrate that these metabolites can all contribute to the methylmalonyl-CoA pool in Streptomyces cinnamonensis, and implicate DNA catabolism as a contributory metabolic source of propionate carbon atoms for secondary metabolite biosynthesis. Further, these labelled compounds were unexpectedly incorporated into the butyrate unit of monensin-A, an observation which can be rationalised if β-aminoisobutyrate is converted to methacrylyl-CoA and then reduced to isobutyryl-CoA prior to conversion to butyryl-CoA by the action of isobutyryl-CoA mutase. Feeding experiments with [1-13C]- and [13C-methyl]-methacrylates and [3-13C]-isobutyrate suggest that these metabolites partition similarly between the butyrate and propionate units of monensin-A consistent with the view that isobutyryl-CoA and methacrylyl-CoA have a close metabolic relationship.

  用同位素标记的[13C, 2H3-甲基]-胸腺嘧啶、(R, S)-[1-13C]-和(R, S)-[13C-甲基]-β-氨基丁酸盐样品喂养莫能菌素-A的实验表明，这些代谢物都能为肉桂链霉菌中的甲基丙二酰-CoA池做出贡献，并暗示DNA分解代谢是次生代谢物生物合成中丙酸碳原子的代谢来源。此外，这些标记化合物出乎意料地掺入了莫能菌素-A 的丁酸单元中，如果 β-氨基丁酸转化为甲基丙烯酰-CoA，然后在异丁烯酰-CoA 突变酶的作用下还原为异丁烯酰-CoA，再转化为丁酰-CoA，那么这一观察结果是合理的。用[1-13C]-和[13C-甲基]-甲基丙烯酸酯和[3-13C]-异丁酸进行的饲喂实验表明，这些代谢物在莫能菌素-A 的丁酸酯和丙酸酯单元之间的分配相似，这与异丁酰基-CoA 和甲基丙烯酰基-CoA 的代谢关系密切的观点一致。
• Franke, Wilfried; Schwarz, Helmut; Thies, Helga, Chemische Berichte, 1981, vol. 114, # 8, p. 2808 - 2824
  作者：Franke, Wilfried、Schwarz, Helmut、Thies, Helga、Chandrasekhar, Jayaraman、Raque' Schleyer, Paul von、et al.

  DOI：——

  日期：——
• Synthesis of isotopically labelled DNA degradation products for use in mass spectrometric studies of cellular DNA damage
  作者：Victor C. Nelson

  DOI：10.1002/(sici)1099-1344(199608)38:8<713::aid-jlcr886>3.0.co;2-i

  日期：1996.8

  Thirteen substituted purines and pyrimidines bearing from three to five carbon, nitrogen and/or deuterium isotopic labels have been synthesized in yields ranging from .1 to 70%. Most of the products originate from the same small number of commercially available labelled starting materials, and in several cases one intermediate leads to two products, thus minimizing the expense and time required. The parent compounds are found in tissue as the result of DNA damage often linked with carcinogenesis and mutagenesis. The synthesized compounds serve as internal standards for the study of DNA damage using mass spectrometry.
• BIE D. A. DE; GEURTSEN B.; BERG I. E.; PLAS H. C. VAN DER, J. ORG. CHEM., 51,(1986) N 16, 3209-3211
  作者：BIE D. A. DE、 GEURTSEN B.、 BERG I. E.、 PLAS H. C. VAN DER

  DOI：——

  日期：——