(±)-ethyl-8,9-dimethoxy-4-methyl-5-oxo-4,5,5a,6-tetrahydronaphtho[3,2,1-cd]indole-5a-carboxylate | 1431885-18-5

• 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: (±)-ethyl-8,9-dimethoxy-4-methyl-5-oxo-4,5,5a,6-tetrahydronaphtho[3,2,1-cd]indole-5a-carboxylate
• CAS: 1431885-18-5
• 化学式: C₂₁H₂₁NO₅
• 分子量: 367.401
• InChiKey: ZEVYEXKPBYMJJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (±)-ethyl 3-(2-bromo-4,5-dimethoxybenzyl)-1-methyl-2-oxoindoline-3-carboxylate 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以76%的产率得到(±)-ethyl-8,9-dimethoxy-4-methyl-5-oxo-4,5,5a,6-tetrahydronaphtho[3,2,1-cd]indole-5a-carboxylate
  参考文献：
  名称：

  DDQ-mediated Direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious Approach to the Tetracyclic Core of Ergot Alkaloids

  摘要：

  An efficient route to 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position has been developed via a DDQ-mediated Intramolecular-Dehydrogenative-Coupling (IDC). The methodology involves a one-pot C-alkylation of beta-N-arylamido esters (7) concomitant with dehydrogenative-coupling in the presence of stoichiometric amount of DDQ. A tentative mechanistic route has been proposed for the oxidative coupling. The methodology provides a two-step entry to the ergoline structure of ergot alkaloids.

  DOI：

  10.1021/ol400899e