6-(Bromomethyl)-1-methyl-1H-indole

• 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: 6-(Bromomethyl)-1-methyl-1H-indole
• 英文别名: 6-(bromomethyl)-1-methylindole
• 化学式: C₁₀H₁₀BrN
• 分子量: 224.1
• InChiKey: SJVRWHKCFUBQIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6-(Bromomethyl)-1-methyl-1H-indole 在 4-二甲氨基吡啶 、 氢氧化钾 、 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 7.67h， 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
• 作为产物：
  描述：

  1-甲基-6-吲哚甲酸甲酯 在 lithium aluminium tetrahydride 、 三溴化磷 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 6-(Bromomethyl)-1-methyl-1H-indole
  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

文献信息

• DNA−Protein Cross-Linking:  Model Systems for Pyrimidine−Aromatic Amino Acid Cross-Linking
  作者：Guangxing Sun、Christopher J. Fecko、Robert B. Nicewonger、Watt W. Webb、Tadhg P. Begley

  DOI：10.1021/ol052876m

  日期：2006.2.1

  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.