6,7-dimethoxy-3-methyl-4-phenylisoquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6,7-dimethoxy-3-methyl-4-phenylisoquinoline
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: CUPFGFIRPUZTDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘-4,5-二甲氧基苯甲醛 在 palladium diacetate 、 水 、 sodium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 6,7-dimethoxy-3-methyl-4-phenylisoquinoline
  参考文献：
  名称：

  Synthesis of Isoquinolines and Pyridines by the Palladium-Catalyzed Iminoannulation of Internal Alkynes

  摘要：

  A wide variety of substituted isoquinoline, tetrahydroisoquinoline, 5,6-dihydrobenz[f]isoquinoline, pyrindine, and pyridine heterocycles have been prepared in good to excellent yields via annulation of internal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst. The best results are obtained by employing 5 mol % of Pd(OAc)(2), an excess of the alkyne, 1 equiv of Na2CO3 as a base, and 10 mol % of PPh3 in DMF as the solvent. This annulation methodology is particularly effective for aryl- or alkenyl-substituted alkynes. When electron-rich imines are employed, this chemistry can be extended to alkyl-substituted alkynes. Trimethylsilyl-substituted alkynes also undergo this annulation process to afford monosubstituted heterocyclic products absent the silyl group.

  DOI：

  10.1021/jo0105540

文献信息

• Palladium-catalyzed annulation of internal alkynes in aqueous medium
  作者：Wei Jie Ang、Chih-Hsuan Tai、Lee-Chiang Lo、Yulin Lam

  DOI：10.1039/c3ra46010j

  日期：——

  To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for carbo- and heteroannulation of internal alkynes with functionalized aryl halides in aqueous medium. A uniform reaction condition for these annulation reactions was also developed.

  为了促进前催化剂的回收和再利用，我们开发了一种氟溶性的、基于肟的钯环化合物1，并证明它是非常高效且多功能的前催化剂，适用于内部炔烃与功能化芳基卤化物在水相介质中的碳环化和杂环化反应。同时，我们还开发了这些环化反应的统一反应条件。