methyl 7-methoxy-3-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate | 1266226-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: methyl 7-methoxy-3-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
• 英文别名: Methyl 7-methoxy-3-methyl-1-oxo-2,4-dihydroisoquinoline-3-carboxylate
• CAS: 1266226-58-7
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: WYCFQFIWPYVPIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  一氧化碳 、 methyl 2-amino-2-methyl-3-(4-methoxyphenyl)propanoate 在 palladium diacetate 、 溶剂黄146 、 对苯醌 作用下， 以72%的产率得到methyl 7-methoxy-3-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
  参考文献：
  名称：

  Preparation of benzolactams by Pd(ii)-catalyzed carbonylation of N-unprotected arylethylamines

  摘要：

  研究人员开发了一种前所未有的 NH2 定向钯（II）催化季芳香族 α-氨基酯羰基化反应，生成 6 元苯内酰胺。与 5 元内酰胺相比，该反应更倾向于 6 元内酰胺。氨基周围的立体阻碍似乎是该过程成功的关键。

  DOI：

  10.1039/c0cc03478a

文献信息

• NH₂ As a Directing Group: From the Cyclopalladation of Amino Esters to the Preparation of Benzolactams by Palladium(II)-Catalyzed Carbonylation of N-Unprotected Arylethylamines
  作者：Joan Albert、Xavier Ariza、Teresa Calvet、Mercé Font-Bardia、Jordi Garcia、Jaume Granell、Andrea Lamela、Blanca López、Manuel Martinez、Laura Ortega、Aleix Rodriguez、David Santos

  DOI：10.1021/om301140t

  日期：2013.1.28

  An unusual NH2-directed Pd(II)-catalyzed carbonylation of quaternary aromatic alpha-amino esters to yield benzolactams has been developed. The steric hindrance around the amino group is pivotal for the success of the process. The stoichiometric cyclometalation of a variety amino esters has been studied in order to evaluate the influence of the different variables (size of the metallacycle, aromatic ring substituents, and steric bulk) in the process, and a complete kinetico-mechanistic study of the cyclopalladation process has been carried out. The experimental results indicate that the full substitution of the carbon in the alpha position of the amino esters plays an important role in their cyclopalladation reaction. The reaction shows a strong bias toward six-membered lactams over the five-membered analogues, which can be explained by a greater reactivity of the six-membered palladacycles.