Acetamino-cyan-essigsaeure | 89188-25-0

• 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: Acetamino-cyan-essigsaeure
• 英文别名: Acetamido-cyanoessigsaeure；acetylamino-cyano-acetic acid；Acetamino-malonsaeure-mononitril；Acetylamino-cyan-essigsaeure；N-Acetyl-3-nitriloalanine；2-acetamido-2-cyanoacetic acid
• CAS: 89188-25-0
• 化学式: C₅H₆N₂O₃
• mdl: MFCD19217524
• 分子量: 142.114
• InChiKey: YRDRLZUCWMJXLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Acetamino-cyan-essigsaeure 在 lithium hydroxide 、 acylase 作用下， 生成 α-Cyan-glycin
  参考文献：
  名称：

  Synthesis and properties of .alpha.-cyanoamino acids. .alpha.-Cyanoglycine, L-.beta.-cyano-.beta.-alanine, and L-.gamma.-cyano-.gamma.-aminobutyric acid

  摘要：

  DOI：

  10.1021/jo00824a024
• 作为产物：
  描述：

  N-乙酰基-2-氰基甘氨酸乙酯 生成 Acetamino-cyan-essigsaeure
  参考文献：
  名称：

  Synthesis and properties of .alpha.-cyanoamino acids. .alpha.-Cyanoglycine, L-.beta.-cyano-.beta.-alanine, and L-.gamma.-cyano-.gamma.-aminobutyric acid

  摘要：

  DOI：

  10.1021/jo00824a024

文献信息

• King, Journal of the American Chemical Society, 1947, vol. 69, p. 2740
  作者：King

  DOI：——

  日期：——
• Studies in Chemotherapy. XIII. Antimalarials. Halogenated Sulfanilamidoheterocycles
  作者：J. P. English、J. H. Clark、J. W. Clapp、Doris Seeger、R. H. Ebel

  DOI：10.1021/ja01207a033

  日期：1946.3
• CN115557951
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and properties of .alpha.-cyanoamino acids. .alpha.-Cyanoglycine, L-.beta.-cyano-.beta.-alanine, and L-.gamma.-cyano-.gamma.-aminobutyric acid
  作者：Charlotte Ressler、G. R. Nagarajan、Makoto Kirisawa、D. V. Kashelikar

  DOI：10.1021/jo00824a024

  日期：1971.12
• Characterization of Metabolites of Fungicidal Cymoxanil in a Sensitive Strain of Botrytis cinerea
  作者：Frederique Tellier、Rene Fritz、Lucien Kerhoas、Paul-Henri Ducrot、Jacques Einhorn、Abel Carlin-Sinclair、Pierre Leroux

  DOI：10.1021/jf8010917

  日期：2008.9.10

  The metabolism of cymoxanil [1-(2-cyano-2-methoxyiminoacetyl)-3-ethyl urea] by a very sensitive strain of Botrytis cinerea toward this fungicide was studied by using [2-(14)C]-cymoxanil. Labeled cymoxanil was added either in a culture of this strain or in its enzymatic extract. The main metabolites, detected in biological samples, were isolated and identified by mass and NMR spectrometry. Their identification allowed us to show that this strain quickly metabolized cymoxanil according to at least three enzymatic pathways: (i) cyclization leading, after hydrolysis, to ethyl parabanic acid, (ii) reduction giving demethoxylated cymoxanil, and (iii) hydrolysis and reduction followed by acetylation leading to N-acetylcyanoglycine. In a cell-free extract of the same strain, only the first and the second enzymatic reactions, quoted above, occurred. Biological tests showed that, among all the metabolites, only N-acetylcyanoglycine is fungitoxic toward this sensitive strain.