methyl (3-phenylisoquinolin-1-ylamino)acetate | 1381953-72-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (3-phenylisoquinolin-1-ylamino)acetate
• 英文别名: methyl 2-(3-phenylisoquinolin-1-ylamino)acetate；Methyl 2-[(3-phenylisoquinolin-1-yl)amino]acetate；methyl 2-[(3-phenylisoquinolin-1-yl)amino]acetate
• CAS: 1381953-72-5
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: MDLWAODFXNHXRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异腈基乙酸甲酯 、 2-phenylethynylbenzaldehyde oxime 在 silver trifluoromethanesulfonate 、 三乙胺 、 gold(I) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以86%的产率得到methyl (3-phenylisoquinolin-1-ylamino)acetate
  参考文献：
  名称：

  Synthesis of 1-Aminoisoquinolines via the Coinage Metal Cocatalyzed Reaction of 2-Alkynylbenzaldoximes with Isocyanoacetates

  摘要：

  An efficient reaction of 2-alkynylbenzaldoximes with 2-isocyanoacetates cocatalyzed by silver triflate and gold(I) chloride is described, providing 1-aminoisoquinolines in good to excellent yields under mild conditions. Mechanistic experiments suggest that the gold(I) cation might play a crucial role in the activation of the isocyanide substrate. The observed reactivity and the unique pathway of substrate activation in the cocatalyzed processes are quite informative for further study.

  DOI：

  10.1055/s-0034-1378654

文献信息

• Facile synthesis of 1-aminoisoquinolines via the tandem reactions of 2-alkynylbenzaldoximes with isothiocyanates
  作者：Wenhai Li、Yue Wang、Tao Lu

  DOI：10.1016/j.tet.2012.06.030

  日期：2012.8

  1-aminoisoquinolines in good to excellent yields is described; this involves the reaction of 2-alkynylbenzaldoximes and isothiocyanates, which is catalyzed by silver triflate in dichloromethane, at room temperature. This transformation involves tandem 6-endo cyclization, [3+2] cycloaddition, and subsequent rearrangement. The simple operational protocol provides a cost-effective, diversity-oriented route to

  本文描述了一种新的，简明而有效的合成1-氨基异喹啉的方法，该方法具有良好的收率和优异的收率。这涉及2-炔基苯甲酰肟和异硫氰酸酯的反应，该反应在室温下由三氟甲磺酸银在二氯甲烷中催化。这种转化涉及串联6-内环化，[3 + 2]环加成，和随后的重排。简单的操作规程为中性，温和条件下的1-氨基异喹啉提供了一种经济高效的，面向多样性的途径。
• Synthesis of 1-Aminoisoquinolines via the Coinage Metal Cocatalyzed Reaction of 2-Alkynylbenzaldoximes with Isocyanoacetates
  作者：Tao Wang、Fei Xiong、Zhiyuan Chen、Rou Li、Danhong Yu、Chenghao Gu

  DOI：10.1055/s-0034-1378654

  日期：——

  An efficient reaction of 2-alkynylbenzaldoximes with 2-isocyanoacetates cocatalyzed by silver triflate and gold(I) chloride is described, providing 1-aminoisoquinolines in good to excellent yields under mild conditions. Mechanistic experiments suggest that the gold(I) cation might play a crucial role in the activation of the isocyanide substrate. The observed reactivity and the unique pathway of substrate activation in the cocatalyzed processes are quite informative for further study.