5-[5-Methoxy-2-oxo-1,2-dihydro-indol-(3E)-ylidene]-1-methyl-imidazolidine-2,4-dione | 137920-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-[5-Methoxy-2-oxo-1,2-dihydro-indol-(3E)-ylidene]-1-methyl-imidazolidine-2,4-dione
• CAS: 137920-71-9
• 化学式: C₁₃H₁₁N₃O₄
• 分子量: 273.248
• InChiKey: MSWGVPVFLAHUOU-MDZDMXLPSA-N

物化性质

• 密度：
  1.462±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.54
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  87.74
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  5-甲氧基靛红 、 diethyl 1-methyl-2,4-dioxoimidazolidine-5-phosphonate 在 三乙胺 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以59%的产率得到5-[5-Methoxy-2-oxo-1,2-dihydro-indol-(3E)-ylidene]-1-methyl-imidazolidine-2,4-dione
  参考文献：
  名称：

  Diethyl 2,4-dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons reagents for the mild and efficient preparation of C-5 unsaturated hydantoin derivatives

  摘要：

  The phosphonates 19 and 20 were prepared from hydantoin and 1-methylhydantoin, respectively, by way of bromination at C-5 and a subsequent Michaelis-Arbuzov reaction with triethyl phosphite. The Horner-Wadsworth-Emmons-type reagents 19 and 20 were found to react readily with aromatic and aliphatic aldehydes, in the presence of a base, to produce C-5 unsaturated hydantoin derivatives 22 and 26, generally in high yield. The products 22 and 26 were frequently isolated as mixtures of E and Z isomers depending upon the identity of the aldehyde and phosphonate. The isomeric configuration of the products was determined from an analysis of NMR spectral data. Long-range C-13-H-1 coupling constants between the C-4 carbonyl of the hydantoin ring and the olefinic proton were found to be diagnostic of isomer geometry. Conditions were also developed that allowed coupling of 19 and 20 with cyclic and acyclic ketones and alpha-dicarbonyl compounds to afford the corresponding olefinic products. C-5 unsaturated hydantoin derivatives are of synthetic utility as precursors to alpha-amino acid derivatives, pyruvates, and the imidazo[4,5-b]quinolin-2-one heterocyclic ring system, a class of potent inhibitors of low Km cAMP phosphodiesterase and the chromophore present in the siderophore azotobactin.

  DOI：

  10.1021/jo00024a036