4-(dimethoxyphosphoryl)-1,3-dimethylisoquinoline 2-oxide | 1449580-14-6

• 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: 4-(dimethoxyphosphoryl)-1,3-dimethylisoquinoline 2-oxide
• 英文别名: 4-Dimethoxyphosphoryl-1,3-dimethyl-2-oxidoisoquinolin-2-ium
• CAS: 1449580-14-6
• 化学式: C₁₃H₁₆NO₄P
• 分子量: 281.248
• InChiKey: YTTDXDSXNZKIAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(dimethoxyphosphoryl)-1,3-dimethylisoquinoline 2-oxide 在 氯化铵 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以75%的产率得到
  参考文献：
  名称：

  Ir(III)-Catalyzed Synthesis of Isoquinoline N-Oxides from Aryloxime and α-Diazocarbonyl Compounds

  摘要：

  An efficient Ir(III)-catalyzed C-H activation and annulations of aryloxime with a-diazocarbonyl compounds has been developed for the synthesis of substituted isoquinoline N-oxides. The reaction proceeds under mild atmospheric conditions, without any external oxidants and releases N-2 and H2O as the byproducts. In addition, synthetic applications of the N-oxide products have been established by performing further functionalization. An interesting dimeric iridacyclic complex allied through a bis-silver carboxylate bridge has been isolated that efficiently catalyzed the reaction.

  DOI：

  10.1021/acs.orglett.5b03462
• 作为产物：
  描述：

  丙酮基膦酸二甲酯 在 对甲苯磺酰叠氮 、 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 potassium carbonate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 12.0h， 生成 4-(dimethoxyphosphoryl)-1,3-dimethylisoquinoline 2-oxide
  参考文献：
  名称：

  Ir(III)-Catalyzed Synthesis of Isoquinoline N-Oxides from Aryloxime and α-Diazocarbonyl Compounds

  摘要：

  An efficient Ir(III)-catalyzed C-H activation and annulations of aryloxime with a-diazocarbonyl compounds has been developed for the synthesis of substituted isoquinoline N-oxides. The reaction proceeds under mild atmospheric conditions, without any external oxidants and releases N-2 and H2O as the byproducts. In addition, synthetic applications of the N-oxide products have been established by performing further functionalization. An interesting dimeric iridacyclic complex allied through a bis-silver carboxylate bridge has been isolated that efficiently catalyzed the reaction.

  DOI：

  10.1021/acs.orglett.5b03462

文献信息

• Rh(III)-Catalyzed Synthesis of Multisubstituted Isoquinoline and Pyridine <i>N</i>-Oxides from Oximes and Diazo Compounds
  作者：Zhuangzhi Shi、Dennis C. Koester、Mélissa Boultadakis-Arapinis、Frank Glorius

  DOI：10.1021/ja406338r

  日期：2013.8.21

  Multisubstituted isoquinoline and pyridine N-oxides have been prepared by Rh(III)-catalyzed cyclization of oximes and diazo compounds via aryl and vinylic C-H activation. This intermolecular annulation involving tandem C-H activation, cyclization, and condensation steps proceeds under mild conditions, obviates the need for oxidants, releases N-2 and H2O as the byproducts, and displays a broad substituent scope.