4-(1-Methyl-1H-indol-6-yl)-3-oxo-butyric acid ethyl ester | 879219-85-9

• 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: 4-(1-Methyl-1H-indol-6-yl)-3-oxo-butyric acid ethyl ester
• CAS: 879219-85-9
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: FOVKDRMXDIYBIN-UHFFFAOYSA-N

物化性质

• 沸点：
  401.4±25.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(1-Methyl-1H-indol-6-yl)-3-oxo-butyric acid ethyl ester 、 尿素 以 二甲基亚砜 为溶剂， 反应 24.0h， 以8%的产率得到6-[(1-Methyl-1H-indol-6-yl)methyl]-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  DNA−Protein Cross-Linking:  Model Systems for Pyrimidine−Aromatic Amino Acid Cross-Linking

  摘要：

  We have synthesized simple model systems to explore the possibility of photo-cross-linking between the pyrimidine bases and the side chains of the aromatic amino acids. Thymine/phenylalanine and thymine/tyrosine models gave cross-links, and thymine/tryptophan models gave complex mixtures; the cytosine/phenylalanine model was unreactive. The quantum yields for the model cross-linking reactions were 18-46 times smaller than those for thymine dimer formation. Biphotonic excitation contributes little to the yield of these reactions.

  DOI：

  10.1021/ol052876m
• 作为产物：
  描述：

  1-甲基-6-吲哚甲酸甲酯 在 4-二甲氨基吡啶 、 氢氧化钾 、 lithium aluminium tetrahydride 、 三溴化磷 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 11.17h， 生成 4-(1-Methyl-1H-indol-6-yl)-3-oxo-butyric acid ethyl ester
  参考文献：
  名称：

  DNA−Protein Cross-Linking:  Model Systems for Pyrimidine−Aromatic Amino Acid Cross-Linking

  摘要：

  We have synthesized simple model systems to explore the possibility of photo-cross-linking between the pyrimidine bases and the side chains of the aromatic amino acids. Thymine/phenylalanine and thymine/tyrosine models gave cross-links, and thymine/tryptophan models gave complex mixtures; the cytosine/phenylalanine model was unreactive. The quantum yields for the model cross-linking reactions were 18-46 times smaller than those for thymine dimer formation. Biphotonic excitation contributes little to the yield of these reactions.

  DOI：

  10.1021/ol052876m