1-(3-butenyl)-9H-β-carboline | 1613694-39-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(3-butenyl)-9H-β-carboline
• 英文别名: 1-but-3-enyl-9H-pyrido[3,4-b]indole
• CAS: 1613694-39-5
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: FRYFDTHLCWDTPS-UHFFFAOYSA-N

物化性质

• 熔点：
  177-179 °C
• 沸点：
  408.5±30.0 °C(predicted)
• 密度：
  1.169±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-butenyl)-9H-β-carboline 在 sodium hydroxide 作用下， 以 甲醇 、 四氯化碳 、 乙醇 为溶剂， 反应 24.75h， 生成 1-(3-butenyl)-2-vinyl-9H-β-carbolinium triflate
  参考文献：
  名称：

  Efficient Synthesis of an Indoloquinolizinium Alkaloid Selective DNA-Binder by Ring-Closing Metathesis

  摘要：

  Two total syntheses of the indolo[2,3-a]quinolizinium cation have been accomplished through the application of two ring-closing metathesis reactions to form the pyridinium ring. One of these approaches provides the tetracyclic cation in only five steps from commercially available harmane. Fluorescence-based thermal denaturation experiments, as well as spectrofluorimetric titration, circular dichroism measurements, and theoretical simulations, showed a consistent DNA-binding capacity by intercalation with a marked preference for AT-rich sequences.

  DOI：

  10.1021/ol5013668
• 作为产物：
  描述：

  N-(2-(1H-indol-3-yl)ethyl)pent-4-enamide 在 三氟甲磺酸酐 、 三苯基氧化膦 、 manganese(IV) oxide 作用下， 以 氯苯 为溶剂， 反应 4.5h， 以8%的产率得到1-(3-butenyl)-9H-β-carboline
  参考文献：
  名称：

  Efficient Synthesis of an Indoloquinolizinium Alkaloid Selective DNA-Binder by Ring-Closing Metathesis

  摘要：

  Two total syntheses of the indolo[2,3-a]quinolizinium cation have been accomplished through the application of two ring-closing metathesis reactions to form the pyridinium ring. One of these approaches provides the tetracyclic cation in only five steps from commercially available harmane. Fluorescence-based thermal denaturation experiments, as well as spectrofluorimetric titration, circular dichroism measurements, and theoretical simulations, showed a consistent DNA-binding capacity by intercalation with a marked preference for AT-rich sequences.

  DOI：

  10.1021/ol5013668

文献信息

• Efficient Synthesis of an Indoloquinolizinium Alkaloid Selective DNA-Binder by Ring-Closing Metathesis
  作者：Beatriz Abarca、Raul Custodio、Ana M. Cuadro、David Sucunza、Alberto Domingo、Francisco Mendicuti、Julio Alvarez-Builla、Juan J. Vaquero

  DOI：10.1021/ol5013668

  日期：2014.7.3

  Two total syntheses of the indolo[2,3-a]quinolizinium cation have been accomplished through the application of two ring-closing metathesis reactions to form the pyridinium ring. One of these approaches provides the tetracyclic cation in only five steps from commercially available harmane. Fluorescence-based thermal denaturation experiments, as well as spectrofluorimetric titration, circular dichroism measurements, and theoretical simulations, showed a consistent DNA-binding capacity by intercalation with a marked preference for AT-rich sequences.