N-butylisoquinolin-1-amine | 46396-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-butylisoquinolin-1-amine
• CAS: 46396-73-0
• 化学式: C₁₃H₁₆N₂
• 分子量: 200.283
• InChiKey: MOYDPHICGXAWEG-UHFFFAOYSA-N

物化性质

• 沸点：
  350.0±17.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲腈 在 aluminum (III) chloride 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver trifluoromethanesulfonate 、 三甲基乙酸钾 作用下， 以 甲苯 为溶剂， 反应 26.0h， 生成 N-butylisoquinolin-1-amine
  参考文献：
  名称：

  通过 Rh 催化的苯甲酰胺与碳酸亚乙烯酯的 [4 + 2] 环化合成氨基异喹啉

  摘要：

  开发了一种用于合成 1-氨基异喹啉衍生物的新策略。这种 Rh(III) 催化的 [4 + 2] 环化反应使用苯甲脒作为有效的导向基团，使用碳酸亚乙烯酯作为乙炔替代物。此外，该反应底物范围广，收率好，只产生碳酸根阴离子作为副产物。

  DOI：

  10.1016/j.cclet.2021.04.058

文献信息

• A mild and metal-free synthesis of 2- and 1-alkyl/aryl/dialkyl-aminoquinolines and isoquinolines
  作者：Yerramsetti Nanaji、Seema Kirar、Sandip V. Pawar、Ashok Kumar Yadav

  DOI：10.1039/c9ra10397j

  日期：——

  A simple synthetic strategy has been developed for the synthesis of 2- and 1-alkyl/aryl/dialkylaminoquinolines and isoquinolines from the easily available quinoline and isoquinoline-N-oxides, different amines, triflic anhydride as activating agent and acetonitrile as solvent in a one-pot reaction under metal-free conditions at 0 °C to room temperature.

  开发了一种简单的合成策略，用于从容易获得的喹啉和异喹啉-N-氧化物、不同的胺、作为活化剂的三氟甲磺酸酐和作为溶剂的乙腈中合成2-和1-烷基/芳基/二烷基氨基喹啉和异喹啉。 -0℃至室温下无金属条件下的罐式反应。
• Synthesis of Bulky and Electron-Rich MOP-type Ligands and Their Applications in Palladium-Catalyzed C−N Bond Formation
  作者：Xiaomin Xie、Tony Y. Zhang、Zhaoguo Zhang

  DOI：10.1021/jo060945k

  日期：2006.8.1

  A series of 2-dialkylphosphino-2'-alkoxy-1,1'-binaphthyl ligands ( 6a-c and 8a-c) have been prepared conveniently by a lithium-initiated ring-opening reaction of dinaphthofuran, followed by selective phosphorylation. These compounds displayed a remarkable air and moisture stability, both in solid form and in solution. Application of these phosphine ligands in palladium-catalyzed C-N bond forming reactions revealed the crucial roles of the steric bulk of the substituents on the phosphorus atom governing the catalytic activity. Specifically, 2-di-tert-butylphosphino-2'-isopropoxy-1, 1'-binaphthyl ( 8b) proved to be the most effective for the aminations of aryl halides with primary amines, while the less bulky 2-dicyclohexyl-2'-methoxy-1,1'-binaphthyl ( 6a) was more effective for the aminations with secondary amines. The steric and electronic effects of the ligands were analyzed to account for these observations.