8-(4-methoxyphenyl)cinnoline | 1562367-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 8-(4-methoxyphenyl)cinnoline
• 英文别名: 8-(4-Methoxyphenyl)cinnoline
• CAS: 1562367-20-7
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: XBMHNWUCHYKWBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  噌啉 、 4-碘苯甲醚 在 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex 、 zinc(II) chloride 、 三(2-呋喃基)膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以84%的产率得到8-(4-methoxyphenyl)cinnoline
  参考文献：
  名称：

  TMP–Magnesium and TMP–Zinc Bases for the Regioselective Metalation of the Cinnoline Scaffold

  摘要：

  A regioselective functionalization of cinnolines in positions 3 and 8 using metalations has been developed. This involves either the use of a frustrated Lewis pair consisting of BF3 center dot Et2O and TMP2Mg center dot 2LiCl or the in situ generated base TMP2Zn center dot 2MgCl(2)center dot 2LiCl. Successive metalations allow the preparation of 3,8-disubstituted cinnolines. Various functionalizations by acylation, allylation, and cross-coupling reactions with aryl halides or alkenyl iodides were carried out successfully.

  DOI：

  10.1021/ol5001999

文献信息

• TMP–Magnesium and TMP–Zinc Bases for the Regioselective Metalation of the Cinnoline Scaffold
  作者：Thomas Klatt、Daniela Sustac Roman、Thierry León、Paul Knochel

  DOI：10.1021/ol5001999

  日期：2014.2.21

  A regioselective functionalization of cinnolines in positions 3 and 8 using metalations has been developed. This involves either the use of a frustrated Lewis pair consisting of BF3 center dot Et2O and TMP2Mg center dot 2LiCl or the in situ generated base TMP2Zn center dot 2MgCl(2)center dot 2LiCl. Successive metalations allow the preparation of 3,8-disubstituted cinnolines. Various functionalizations by acylation, allylation, and cross-coupling reactions with aryl halides or alkenyl iodides were carried out successfully.